AU2001249792A1 - Topical compositions containing prostaglandin E1 - Google Patents

Topical compositions containing prostaglandin E1

Info

Publication number: AU2001249792A1
Authority: AU; Australia
Prior art keywords: accordance; topical composition; composition; penetration enhancer; prostaglandin
Prior art date: 2000-04-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

AU2001249792A

Other languages

English (en)

Inventor

Nadir Buyuktimkin

Servet Buyuktimkin

James L. Yeager

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nexmed Holdings Inc

Original Assignee

Nexmed Holdings Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-04-04

Filing date

2001-04-04

Publication date

2001-10-15

2001-04-04 Application filed by Nexmed Holdings Inc filed Critical Nexmed Holdings Inc

2001-10-15 Publication of AU2001249792A1 publication Critical patent/AU2001249792A1/en

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 161
230000000699 topical effect Effects 0.000 title claims description 53
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 title claims description 6
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 title description 3
229960000711 alprostadil Drugs 0.000 title description 3
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 title 1
150000003180 prostaglandins Chemical class 0.000 claims description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
HSMMSDWNEJLVRY-INIZCTEOSA-N dodecyl (2s)-2-(dimethylamino)propanoate Chemical compound CCCCCCCCCCCCOC(=O)[C@H](C)N(C)C HSMMSDWNEJLVRY-INIZCTEOSA-N 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 28
239000003961 penetration enhancing agent Substances 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 26
150000002634 lipophilic molecules Chemical class 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
-1 alkyl (N,N-disubstituted amino) -acetate Chemical class 0.000 claims description 19
MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 claims description 18
239000007853 buffer solution Substances 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 16
229920001282 polysaccharide Polymers 0.000 claims description 15
229920002125 Sokalan® Polymers 0.000 claims description 14
239000003995 emulsifying agent Substances 0.000 claims description 14
150000004676 glycans Chemical class 0.000 claims description 14
239000005017 polysaccharide Substances 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 13
229920000161 Locust bean gum Polymers 0.000 claims description 10
235000010420 locust bean gum Nutrition 0.000 claims description 10
239000000711 locust bean gum Substances 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
229920000926 Galactomannan Polymers 0.000 claims description 9
OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical group O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
229960001631 carbomer Drugs 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 claims description 3
KTPHASGENPMMQK-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(C)CN(C)C KTPHASGENPMMQK-UHFFFAOYSA-N 0.000 claims description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
KIPQYJOLEGBNHQ-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)CN(C)C KIPQYJOLEGBNHQ-UHFFFAOYSA-N 0.000 claims description 2
229920002907 Guar gum Polymers 0.000 claims description 2
229930006000 Sucrose Natural products 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
IHSPMDXQWYKHOA-UHFFFAOYSA-N dodecyl 2-(dimethylamino)acetate Chemical compound CCCCCCCCCCCCOC(=O)CN(C)C IHSPMDXQWYKHOA-UHFFFAOYSA-N 0.000 claims description 2
239000000665 guar gum Substances 0.000 claims description 2
235000010417 guar gum Nutrition 0.000 claims description 2
229960002154 guar gum Drugs 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
229920005862 polyol Polymers 0.000 claims description 2
150000003077 polyols Chemical class 0.000 claims description 2
239000005720 sucrose Substances 0.000 claims description 2
IPWWTXFQEUNUNX-UHFFFAOYSA-N dodecyl 2-(dimethylamino)propanoate;hydrochloride Chemical group Cl.CCCCCCCCCCCCOC(=O)C(C)N(C)C IPWWTXFQEUNUNX-UHFFFAOYSA-N 0.000 claims 4
NNWXNIVENWLRQA-UHFFFAOYSA-N dodecyl 2-(dimethylamino)propanoate;sulfuric acid Chemical group OS(O)(=O)=O.CCCCCCCCCCCCOC(=O)C(C)N(C)C NNWXNIVENWLRQA-UHFFFAOYSA-N 0.000 claims 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
230000035515 penetration Effects 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000004615 ingredient Substances 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
230000000052 comparative effect Effects 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000003814 drug Substances 0.000 description 12
239000003623 enhancer Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 11
239000002585 base Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
239000000376 reactant Substances 0.000 description 8
238000005809 transesterification reaction Methods 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
230000002459 sustained effect Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000000872 buffer Substances 0.000 description 6
230000001186 cumulative effect Effects 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
241000270295 Serpentes Species 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
UPGMLKNCPUCDSU-UHFFFAOYSA-N ethyl 2-(dimethylamino)propanoate Chemical compound CCOC(=O)C(C)N(C)C UPGMLKNCPUCDSU-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000008901 benefit Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000011068 loading method Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000013459 approach Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 2
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
240000008886 Ceratonia siliqua Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
235000017367 Guainella Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
208000018262 Peripheral vascular disease Diseases 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000013019 agitation Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
238000012377 drug delivery Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000012844 infrared spectroscopy analysis Methods 0.000 description 2
230000000622 irritating effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000149 penetrating effect Effects 0.000 description 2
239000004584 polyacrylic acid Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012453 solvate Substances 0.000 description 2
230000008093 supporting effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
230000037317 transdermal delivery Effects 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
VTCLFBZXKIZNKS-UHFFFAOYSA-N 2,6-diamino-5-iminopyrimidin-4-one Chemical compound NC1=NC(=O)C(=N)C(N)=N1 VTCLFBZXKIZNKS-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
235000013912 Ceratonia siliqua Nutrition 0.000 description 1
108090000317 Chymotrypsin Proteins 0.000 description 1
125000003423 D-mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
229920000569 Gum karaya Polymers 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
102000019280 Pancreatic lipases Human genes 0.000 description 1
108050006759 Pancreatic lipases Proteins 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
206010040880 Skin irritation Diseases 0.000 description 1
241000934878 Sterculia Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
239000000420 anogeissus latifolia wall. gum Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
WMHOESUUCMEQMS-UHFFFAOYSA-L bis[(2,2,2-trifluoroacetyl)oxy]mercury Chemical compound [Hg+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F WMHOESUUCMEQMS-UHFFFAOYSA-L 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
229910000011 cadmium carbonate Inorganic materials 0.000 description 1
GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 1
CNYFJCCVJNARLE-UHFFFAOYSA-L calcium;2-sulfanylacetic acid;2-sulfidoacetate Chemical compound [Ca+2].[O-]C(=O)CS.[O-]C(=O)CS CNYFJCCVJNARLE-UHFFFAOYSA-L 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000002144 chemical decomposition reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 1
229960002376 chymotrypsin Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000000254 damaging effect Effects 0.000 description 1
238000002716 delivery method Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
229960001673 diethyltoluamide Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
150000004862 dioxolanes Chemical class 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
IPWWTXFQEUNUNX-NTISSMGPSA-N dodecyl (2s)-2-(dimethylamino)propanoate;hydrochloride Chemical compound Cl.CCCCCCCCCCCCOC(=O)[C@H](C)N(C)C IPWWTXFQEUNUNX-NTISSMGPSA-N 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
FGBGMOBXVFWPCI-UHFFFAOYSA-N ethyl dodecanoate;tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCC(=O)OCC FGBGMOBXVFWPCI-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000004907 flux Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000451 gelidium spp. gum Substances 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
235000019314 gum ghatti Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
KUQWZSZYIQGTHT-UHFFFAOYSA-N hexa-1,5-diene-3,4-diol Chemical compound C=CC(O)C(O)C=C KUQWZSZYIQGTHT-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
230000001976 improved effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
229940074928 isopropyl myristate Drugs 0.000 description 1
235000010494 karaya gum Nutrition 0.000 description 1
239000000231 karaya gum Substances 0.000 description 1
229940039371 karaya gum Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
229940116369 pancreatic lipase Drugs 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
231100000435 percutaneous penetration Toxicity 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000012466 permeate Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical group CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
229940107644 prostin vr Drugs 0.000 description 1
239000008213 purified water Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
210000003370 receptor cell Anatomy 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
230000037380 skin damage Effects 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
238000002791 soaking Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000003860 topical agent Substances 0.000 description 1
RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Gynecology & Obstetrics (AREA)
Reproductive Health (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Urology & Nephrology (AREA)
Inorganic Chemistry (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

AU2001249792A 2000-04-04 2001-04-04 Topical compositions containing prostaglandin E1 Abandoned AU2001249792A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US09542668		2000-04-04
US09/542,668 US6414028B1 (en)	1997-11-05	2000-04-04	Topical compositions containing prostaglandin E1
PCT/US2001/010699 WO2001074279A1 (fr)	2000-04-04	2001-04-04	Compositions topiques contenant de la prostaglandine e¿1?

Publications (1)

Publication Number	Publication Date
AU2001249792A1 true AU2001249792A1 (en)	2001-10-15

Family

ID=24164793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001249792A Abandoned AU2001249792A1 (en)	2000-04-04	2001-04-04	Topical compositions containing prostaglandin E1

Country Status (15)

Country	Link
US (1)	US6414028B1 (fr)
EP (1)	EP1278495A4 (fr)
JP (1)	JP2004514646A (fr)
KR (1)	KR20030060769A (fr)
CN (1)	CN1203895C (fr)
AU (1)	AU2001249792A1 (fr)
BR (1)	BR0109863A (fr)
CA (1)	CA2405293A1 (fr)
HU (1)	HUP0302452A2 (fr)
IL (1)	IL152084A0 (fr)
MX (1)	MXPA02009798A (fr)
NZ (1)	NZ522363A (fr)
TR (1)	TR200202308T2 (fr)
WO (1)	WO2001074279A1 (fr)
ZA (1)	ZA200208803B (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050004226A1 (en) *	1998-12-10	2005-01-06	Nexmed (Holdings), Inc.	Compositions and methods for amelioration of human female sexual dysfunction
US6825234B2 (en)	1998-12-10	2004-11-30	Nexmed (Holdings) , Inc.	Compositions and methods for amelioration of human female sexual dysfunction
EA008720B1 (ru) *	1998-12-10	2007-06-29	Нексмед (Холдингс), Инк.	Применение композиции на основе простагландина для лечения расстройства сексуального возбуждения у женщин
US6693135B2 (en) *	2000-01-10	2004-02-17	Nexmed (Holdings) Incorporated	Prostaglandin compositions and methods of treatment for male erectile dysfunction
US7105571B2 (en) *	2000-01-10	2006-09-12	Nexmed Holdings, Inc.	Prostaglandin compositions and methods of treatment for male erectile dysfunction
US6673841B2 (en) *	2001-12-20	2004-01-06	Whan In Pharm. Co., Ltd.	Alprostadil alkyl ester-containing composition for external application
CA2468631A1 (fr) *	2002-02-15	2003-08-28	Nexmed (Holdings), Inc.	Composition de prostaglandine pour le traitement des troubles de l'erection
GB0222522D0 (en)	2002-09-27	2002-11-06	Controlled Therapeutics Sct	Water-swellable polymers
US6841574B2 (en) *	2003-01-03	2005-01-11	Nexmed Holdings, Inc.	Topical stabilized prostaglandin E compound dosage forms
US20050181030A1 (en) *	2003-01-03	2005-08-18	Mo Y. J.	Topical stabilized prostaglandin E compound dosage forms
AU2004224413A1 (en) *	2003-03-21	2004-10-07	Nexmed (Holdings), Inc.	Prostaglandin compositions for the treatment of erectile dysfunction
KR20050119136A (ko) *	2003-03-21	2005-12-20	넥스메드 홀딩스 인코포레이티드	프로스타글란딘 조성물에 의한 혈관형성 촉진 및 방법
EP1608378A1 (fr) *	2003-04-02	2005-12-28	Nexmed (Holdings), Inc.	Compositions de prostaglandine et leur utilisation dans le traitement du spasme vasculaire
GB0315671D0 (en) *	2003-07-04	2003-08-13	Chelsea And Westminster Nhs Tr	Improvements in or relating to organic compounds
US20060204526A1 (en) *	2003-08-13	2006-09-14	Lathrop Robert W	Emulsive composition containing Dapsone
US20050113274A1 (en) *	2003-11-22	2005-05-26	Nadir Buyuktimkin	Hydrocarbyl aminohydrocarbonoates and aminohydrocarbonol hydrocarbonoates as antimicrobial and antiviral agents
GB0417401D0 (en) *	2004-08-05	2004-09-08	Controlled Therapeutics Sct	Stabilised prostaglandin composition
EP1998742A2 (fr) *	2006-03-08	2008-12-10	Nuviance, INC.	Composition de médicament à libération transdermique et compositions topiques pour application cutanée
GB0613333D0 (en)	2006-07-05	2006-08-16	Controlled Therapeutics Sct	Hydrophilic polyurethane compositions
GB0613638D0 (en)	2006-07-08	2006-08-16	Controlled Therapeutics Sct	Polyurethane elastomers
US7560489B2 (en) *	2006-10-11	2009-07-14	Nexmed Holdings, Inc.	Stabilized prostaglandin E composition
GB0620685D0 (en)	2006-10-18	2006-11-29	Controlled Therapeutics Sct	Bioresorbable polymers
JP5297631B2 (ja) *	2007-11-13	2013-09-25	花王株式会社	皮膚外用組成物
US9220701B2 (en)	2008-10-03	2015-12-29	Nexmed Holdings, Inc.	Stabilized composition for treating psoriasis
MX2012012824A (es) *	2010-05-04	2013-07-03	Nexmed Holdings Inc	Composiciones de productos terapeuticos de moleculas pequeñas.
BR112013025744A2 (pt)	2011-04-07	2016-08-16	Nexmed Holdings Inc	composicões para tratamento da doença de raynaud
ITRM20120036A1 (it)	2012-02-02	2013-08-03	Robert Davis Steigerwalt Jr	Applicazione transdermica di prostaglandina e1 per il trattamento dell¿ischemia oculare.
MY209082A (en) *	2020-03-11	2025-06-19	Advansix Resins & Chemicals Llc	Surfactants for healthcare products
US11912930B2 (en)	2020-03-11	2024-02-27	Advansix Resins & Chemicals Llc	Formulation for the recovery of hydrocarbons including a surfactant system

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK243084A (da)	1983-05-26	1984-11-27	Takeda Chemical Industries Ltd	Perkutane farmaceutiske praeparater til udvortes brug
GB8416638D0 (en)	1984-06-29	1984-08-01	Beecham Group Plc	Topical treatment and composition
US4732892A (en)	1985-07-12	1988-03-22	American Home Products Corporation	L-α-amino acids as transdermal penetration enhancers
US4771004A (en)	1986-08-29	1988-09-13	Iprx, Inc.	Method for in vitro determination of transdermal absorption
US4808414A (en)	1986-09-29	1989-02-28	Nelson Research & Development Co.	Amide penetration enhancers for transdermal delivery of systemic agents
US4865848A (en)	1987-02-26	1989-09-12	Alza Corporation	Skin permeation enhancer compositions using sucrose esters
US4980378A (en)	1988-06-01	1990-12-25	Odontex, Inc.	Biodegradable absorption enhancers
US5082866A (en)	1988-06-01	1992-01-21	Odontex, Inc.	Biodegradable absorption enhancers
US5534260A (en)	1989-02-23	1996-07-09	University Of Utah	Percutaneous drug delivery system
US4973468A (en)	1989-03-22	1990-11-27	Cygnus Research Corporation	Skin permeation enhancer compositions
JP3202777B2 (ja)	1992-01-24	2001-08-27	リンテック株式会社	経皮吸収促進剤及びテープ製剤
ATE399004T1 (de)	1993-12-13	2008-07-15	Avanir Pharmaceuticals	Formulierungen aus c-20 bis c-28 alkoholen und saccharoseestern
US6083996A (en) *	1997-11-05	2000-07-04	Nexmed Holdings, Inc.	Topical compositions for NSAI drug delivery
US6046244A (en) *	1997-11-05	2000-04-04	Nexmed Holdings, Inc.	Topical compositions for prostaglandin E1 delivery
US5942545A (en) *	1998-06-15	1999-08-24	Macrochem Corporation	Composition and method for treating penile erectile dysfunction
JP2002523144A (ja) *	1998-08-20	2002-07-30	スリーエムイノベイティブプロパティズカンパニー	包帯への噴霧および薬物送達システム
US6118020A (en) *	1999-05-19	2000-09-12	Nexmed Holdings, Inc.	Crystalline salts of dodecyl 2-(N,N-dimethylamino)-propionate
US6323241B1 (en) *	2000-01-10	2001-11-27	Nexmed (Holdings) Inc.	Prostaglandin compositions and methods of treatment for male erectile dysfunction

2000
- 2000-04-04 US US09/542,668 patent/US6414028B1/en not_active Expired - Lifetime
2001
- 2001-04-04 IL IL15208401A patent/IL152084A0/xx unknown
- 2001-04-04 BR BR0109863-2A patent/BR0109863A/pt not_active IP Right Cessation
- 2001-04-04 CN CNB018103162A patent/CN1203895C/zh not_active Expired - Fee Related
- 2001-04-04 TR TR2002/02308T patent/TR200202308T2/xx unknown
- 2001-04-04 HU HU0302452A patent/HUP0302452A2/hu unknown
- 2001-04-04 KR KR1020027013295A patent/KR20030060769A/ko not_active Withdrawn
- 2001-04-04 EP EP01923062A patent/EP1278495A4/fr not_active Withdrawn
- 2001-04-04 JP JP2001572026A patent/JP2004514646A/ja not_active Withdrawn
- 2001-04-04 AU AU2001249792A patent/AU2001249792A1/en not_active Abandoned
- 2001-04-04 CA CA002405293A patent/CA2405293A1/fr not_active Abandoned
- 2001-04-04 NZ NZ52236301A patent/NZ522363A/xx unknown
- 2001-04-04 WO PCT/US2001/010699 patent/WO2001074279A1/fr not_active Ceased
2002
- 2002-10-04 MX MXPA02009798A patent/MXPA02009798A/es unknown
- 2002-10-30 ZA ZA200208803A patent/ZA200208803B/en unknown

Also Published As

Publication number	Publication date
CN1203895C (zh)	2005-06-01
ZA200208803B (en)	2003-12-19
KR20030060769A (ko)	2003-07-16
JP2004514646A (ja)	2004-05-20
TR200202308T2 (tr)	2005-07-21
BR0109863A (pt)	2004-09-28
EP1278495A4 (fr)	2006-03-22
CA2405293A1 (fr)	2001-10-11
CN1449270A (zh)	2003-10-15
US6414028B1 (en)	2002-07-02
WO2001074279A1 (fr)	2001-10-11
EP1278495A1 (fr)	2003-01-29
MXPA02009798A (es)	2003-05-27
HK1059558A1 (en)	2004-07-09
IL152084A0 (en)	2003-05-29
NZ522363A (en)	2004-12-24
HUP0302452A2 (hu)	2003-11-28

Publication	Publication Date	Title
US6414028B1 (en)	2002-07-02	Topical compositions containing prostaglandin E1
EP1028708B1 (fr)	2010-01-20	Compositions topiques pour l'administration de prostaglandine e1
EP1585483B1 (fr)	2010-05-19	Formes posologiques de compose topique stabilise de prostaglandine e
US4847260A (en)	1989-07-11	Composition for percutaneous administration
EP0788794A1 (fr)	1997-08-13	Composition pour preparation a usage externe
EP0600395A1 (fr)	1994-06-08	Gel anti-inflammatoire et analgésique de diclofenac
CZ102797A3 (cs)	1998-10-14	Sloučeniny na bázi omega-aminokyselin, způsob jejich přípravy jejich použití jako akcelerantů transdermální penetrace a akceleranty transdermální penetrace těmito sloučeninami tvořené
JPH0611715B2 (ja)	1994-02-16	経皮吸収促進剤およびこれを含有する外用剤
CA2442479C (fr)	2005-12-13	Compositions topiques d'apport de prostaglandine e1
EP0309624B1 (fr)	1992-03-11	Composition pour améliorer l'administration percutanée d'un médicament
JP3098275B2 (ja)	2000-10-16	トルナフテート含有液剤
WO2010049485A2 (fr)	2010-05-06	Formulations topiques de 3-(2,2,2-trimethylhydrazinium) propionate dihydrate
HK1034678B (en)	2005-10-14	Topical compositions for prostaglandin e1 delivery
HK1059558B (en)	2006-01-13	Topical compositions containing prostaglandin e1