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PL130564B1 - Process for preparing unit pharmaceutical dose containing lyophilized sodium piperacylin - Google Patents

Process for preparing unit pharmaceutical dose containing lyophilized sodium piperacylin Download PDF

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PL130564B1
PL130564B1 PL1982235509A PL23550982A PL130564B1 PL 130564 B1 PL130564 B1 PL 130564B1 PL 1982235509 A PL1982235509 A PL 1982235509A PL 23550982 A PL23550982 A PL 23550982A PL 130564 B1 PL130564 B1 PL 130564B1
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concentration
water
lyophilized
piperacillin sodium
solution
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PL235509A1 (en
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American Cyanamid Co
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425Thiazoles
    • A61K31/429Thiazoles condensed with heterocyclic ring systems
    • A61K31/43Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents

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  • Veterinary Medicine (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Przedmiotem wynalazku jest sposób wytwarza¬ nia dawki jednostkowej do podawania pozajelito¬ wego zawierajacej sól sodowa kwasu 6-(2-)4-etylo- -2,3-diokso-l-piperazynokarboksyamido)-2-fenylo- acet*amido)-3,3-dimetylo-7-okso-4-tia-l-azabicy- klo[3.2.0]heptano-2-karboksylowego, zwana dalej piperacylina sodu. Sól ta jest opisana w opisie pa¬ tentowym Stanów Zjednoczonych Ameryki nr 4112090, w którym wykazano jej wykorzystywanie jako srodka przeciwbakteryjnego.Konwencjonalny sposób wytwarzania liofilizowa¬ nej dawki leku do podawania pozajelitowego pole¬ ga na wytworzeniu 200 mg/ml wodnego roztVoru pochodnej penicyliny, napelnieniu tym roztworem ampulek w ilosci 5 ml na ampulke a nastepnie lio¬ filizowaniu zawartosci ampulek. Wysuszony placek jest odpowiednikiem jednego gramu pochodnej pe¬ nicyliny. Gdy lekarz przygotowuje sie do podania leku, odtwarza fiolke 3,3 ml wody lub innego od¬ powiedniego rozcienczalnika. Pochodna penicyliny zajmuje miejsce 0,7 ml rozcienczalnika na gram pochodnej. Koncowy produkt stanowi zatem 4,0 ml odtworzonej pochodnej penicyliny o stezeniu 250 mg/ml. Nastepnie lekarz pobiera odpowiednia ilosc roztworu z fiolki do strzykawki i podaje odpowied¬ nia dawke pacjentowi.Trudnosc przy stosowaniu powyzszej kompozycji pozajelitowej stanowi fakt, ze lekarz musi poda¬ wac 4 ml roztworu na 1 gram dawki. Piperacyli¬ na podobnie jak wiele pochodnych penicyliny jest 10 15 20 25 30 l\ipertbniczna a zatem powoduje ból przy iniekcji domiesniowej. Ponadto limit dawki do iniekcji do ramienia wynosi okolo 2 ml, poniewaz umiesnienie zwykle nie znosi wiekszych objetosci sródmiazszo- wych. Dlatego dawka 4 ml narzuca koniecznosc mniej dogodnych iniekcji do posladków. Nawet przy iniekcji do posladków, duza dawka 4 ml sprawia, ze zwieksza sie czas rozprowadzania leku.Celem wynalazku jest opracowanie takiej formy pozajelitowej dawki jednostkowej piperacyliny so¬ du, która zmniejszy objetosc dawki do iniekcji w porównaniu ze znana dawka przez zapewnienie wiekszego stezenia produkfu koncowego.Trudnosc z wytwarzaniem stezonego odtwarzane¬ go preparatu liofilizowanej leku polega na tym, ze gdy stezenie koncowego produktu rosnie, wzrasta takze czas odtwarzania. Dla stezenia produkfu kon¬ cowego 400 mg/ml czas odtwarzania wynosi kilka minut przy ciaglym wytrzasaniu. Czas wymagany do odtwarzania takich produktów prowadzil do zniechecenia do ich stosowania, powodujac, ze sto¬ sowano preparaty bardziej rozcienczone ze wszy¬ stkimi ich niekorzystnymi cechami opisanymi po¬ wyzej.Innym celem wynalazku jest sporzadzenie formy liofilizowanej dawki pozajelitowej piperacyliny so¬ du o wyzszym stezeniu, w której produkt konco¬ wy bedzie latwiej odtwarzany.Pozajelitowa dawka jednostkowa otrzymywana sposobem wedlug wynalazku zawiera sypki, puszy- 130 564130 564 3 4 sty, porowaty placek liofilizowanej soli sodowej kwasu 6-(2-)4-etylo-2,3-diokso-l-piperazynokarbo- ksyamido)-2-fenyloacetamido)-3,3^dimetylo-7-okso- -4-tia-l-azabicyklo[3.2.0]heptano-2-karboksylowego zwanej piperacylina sodu. Okreslenie „porowaty placek", oznacza liofilizowany placek który zajmuje wieksza objetosc niz „placek standardowy".Wedlug wynalazku, sposób wytwarzania jedno¬ stkowej farmaceutycznej dawki do podawania po¬ zajelitowego zawierajacej piperacyline sodu obej¬ muje przygotowanie roztworu piperacyliny sadu w wodzie, napelnienie tym roztworem pojemnika do wymaganej ilosci i liofilizacje, przy czym cecha znamienna jest to, ze roztwór piperacyliny sodu w wodzie przygotowuje sie w stezeniu od 100 mg/ml do 135 mg/ml, korzystnie 125 mg/ml. Na konkret¬ nym przykladzie, realizacja rozwiazania objetego zastrzezeniem wyglada nastepujaco: piperacyline sodu rozpuszcza sie w wodzie do stezenia 126 mg/ml. 8 ml tego roztworu napelnia sie fiolke do calkowi¬ tej ilosci 1 g piperacyliny sodu w fiolce. Stosuje sie fiolki, poniewaz dobrze znosza proces liofilizacji i nadaja sie do zamykania odpowiednimi korkami, które pozwalaja na pobieranie zawartosci strzykaw¬ ka.Nastepnie piperacyline sodu zamraza sie i lio¬ filizuje w fiolkach zgodnie ze znanym standardo¬ wym procesem. Podczas liofilizacji, suszony subli¬ macyjnie placek zachowuje objetosc cieklej dawki i tworzy krystaliczna sypka mase o ukierunkowa¬ nej strukturze, zamknieta pod próznia. Poniewaz objetosc nalanej cieczy wynosi 8 ml, liofilizowany placek jest duzo wiekszy i luzniejszy („porowaty placek") niz 5 ml-owy placek otrzymywany trady¬ cyjnie, liofilizowane fiolki uszczelnia sie odpowied¬ nimi koreczkami.Gdy lekarz przygotowuje sie do podawania leku, odtwarza liofilizowany placek 2,5 ml odpowiednie¬ go rozcienczalnika. Przykladami odpowiednich roz¬ cienczalników sa na przyklad woda lub chlorowo¬ dorek lidocainy, miejscowy srodek znieczulajacy, który mozna dodawac dla przeciwdzialania bólowi przy iniekcji spowodowanemu hipertondczna wla¬ sciwoscia piperacyliny. Czas niezbedny do odtwo- 10 15 20 25 30 35 40 rzenia 1 g liofilizowanej piperacyliny sodu wynosi okolo 35 sekund przy wytrzasaniu. Koncowy pro¬ dukt zawiera 2,5 ml roztworu o stezeniu 400 mg/ml, piperacyliny sodu i dawke iniekcyjna 2,5 ml/g w przeciwienstwie do dawki poprzedniej wynoszacej 4 ml/g.Opisany powyzej sposób mozna modyfikowac otrzymujac wieksza lub mniejsza ilosc koncowego produktu przez proporcjonalne zwiekszenie lub zmniejszenie ilosci 125 mg/ml cieczy wprowadzanej do fiolki przed liofilizacja, i przez proporcjonalne zwiekszenie lub zmniejszenie ilosci rozcienczalni¬ ka potrzebnego do odtworzenia koncowego produk¬ tu o stezeniu koncowym 400 mg/ml.Opisany powyzej proces mozna równiez modyfi¬ kowac stosujac ciecz do napelniania o stezeniu wyzszym lub nizszym niz 125 mg/ml chociaz z mniejszym powodzeniem. Wieksze stezenie cieczy zwieksza gestosc liofilizowanego placka i zwieksza takze czas odtwarzania niezbedny do rozpuszczenia piperacyliny do stezenia 400 mg/ml lecz niewspól¬ miernie wiele. Na przyklad, zwiekszenie stezenia napelnianej cieczy o 15% powoduje zwiekszenie cza¬ su odtwarzania ponad 100%. (patrz Przyklad III).Alternatywnie mozna stosowac nizsze stezenie cie¬ czy lecz nizsze stezenie cieczy powoduje wieksza objetosc cieczy niezbedna do otrzymania danej ilo¬ sci liofilizowanej leku i wymaga wiekszej fiolki do liofilizacji. Jezeli stosuje sie bardziej rozcienczona ciecz, niezbedna jest bardzo duza fiolka do napel¬ nienia jej proporcjonalnie wieksza objetoscia cieczy i koncowy produkt po odtworzeniu do stezenia 400 mg/ml bedzie zajmowal tylko stosunkowo niewiel¬ ka czesc calej objetosci fiolki. Praktycznie, stezenie cieczy powinno byc w zakresie 100—(135 mg/ml, ko¬ rzystnie okolo 125 mg/ml.Przedmiot wynalazku jest blizej objasniony w przykladach wykonania, które nie ograniczaja jego zakresu.Przyklad I. Oznaczanie optymalnego stezenia koncowego produktu — 2 g/fiolke.Sól sodowa kwasu 6-/2^(4-el!ylo-2,3-diokso-l-pipe- razynokarboksyamido)-2-fenyloacetamido/-3,3-di- metylo-7-okso-4-tia-l-azabicykio [3.2.0]heptano-2- Tablica I Prób¬ ka 1 1 % a 4 Ilosc ml wfcdy do odtwo¬ rzenia 8,6 6,6 3,6 2,6 a | 1,93..Kon¬ cowa obje¬ tosc ml 10 8 5 4 3,33 Koncowe stezenie w mg/ml 200 200 400 £00 600 | Sredni czas rozpuszcza¬ nia min 0,5 0,5 . 2,0 5,75 25—30 pH 5,87 5,95 6,09 6,16 6^27 Gejstosc 1,0.72 1,090 1,141 1,173 1,206 Lepkosc cp 2,6 3,8 1$,2 65 314 | Czas napelniania strzykawki 26 prób dobry dobry dostatecz- i ny slaby slaby | 21 prób dobry dobry dobry 1 dostatecz- 1 ny 1 slaby 1 Kazdy gram piperacyliny sodu zajmuje miejsce 0,7 ml wody Badanie czasu napelniania strzykawki: dobry 5— 15 sekund do nabrania 1 ml dostateczny 20—30 sekund do nabrania 1 ml slaby 1 minuty do nabrania 1 ml5 130 564 6 -karboksylowego rozpuszczono w wodzie do steze¬ nia 200 mg/ml. 10 ml tego roztworu napelniono kaz¬ da z pieciu fiolek i liofilizowano je standardowa metoda. Nastepnie kazdy z tych liofilizowanych placków odtwarzano za pomoca róznych ilosci wo¬ dy otrzymujac serie koncowych stezen piperacyli- ny sodu uwzgledniajac fakt, ze kazdy gram pipe- racyliny sodu zajmuje miejsce 0,7 ml wody. Bada¬ no pH, gestosc i lepkosc tych produktów standar¬ dowymi metodami. Czas rozpuszczania mierzono wytrzasajac w reku fiolki zawierajace liofilizowa¬ ny placek i wode dodana do odtworzenia i mierzac czas niezbedny do przejscia piperacyliny sodu do roztworu. Okreslano równiez czas konieczny do na¬ brania 1 ml koncowego produktu z fiolki do strzy¬ kawki. Wyniki zestawiono w Tablicy I.Przyklad II. Oznaczanie optymalnego steze¬ nia koncowego produktu — 1 g/fiolke.Sposobem opisanym w Przykladzie I napelniono Tablica II Prób¬ ka V 2 3 4 i5 • Ilosc ml wody do odtwo¬ rzenia 4,3 3,3 1,8 1,3 0,97 Kon¬ cowa obje¬ tosc ml 5 4 2,5 2,0 1,67 Koncowe stezenie w mg/ml 200 250 400 500 600 Sredni czas rozpuszcza¬ nia min 0,75 0,75 2,75 8,5 25—30 PH 5,83 5,92 6,0^ 6,16 6,26 Gestosc 1,073 1,090 1,141 1,175 1,208 Lepkosc cp 2,6 3,8 16,2 65 317 Czas napelniania strzykawki 26 prób dofbry dobry dostatecz¬ ny slaby slaby 21 prób dobry dobry dobry dostatecz¬ ny slaby | Kazdy ml piperacyliny sodu zajmuje miejsce 0,7 ml wody Badanie czasu napelniania strzykawki: dobry 5—15 sekund do nabrania 1 ml dostateczny 20—30 sekund do nabrania 1 ml slaby 1 minuty do nabrania 1 ml Tablica III Próbka i 2 1 3 1 4 Stezenie napelniania mg/ml 200 166,7 142,9 125 Ilosc ml we fiolce 5 6 7 8 Odtwarzanie ilosc ml wody 1,8 1,8 1,8 1,8 stezenie koncowe mg/ml 400 400 400 400 Sredni czas odtwarzania 1 min 42 sek 1 min 16 sek 36 sek 15 sek [ Kazdy gram piperacyliny sodu zajmuje miejsce 0,7 ml wody Tablica IV Oznaczenie fiolki 1 2 3 4 6 Ilosc ml roztworu o stezeniu 125 mg/ml 8,64 17,28 25,92 34,24 50,56 | Ilosc mg we fiolce iiiii Ilosc ml do1 odtworzenia do 400 mg/ml 2,0 4,0 6,0 7,8 11,6 Stezenie konco¬ we w mg/ml 400 400 400 404 400 1 kazda z pieciu fiolek 5 ml 200 mg/ml roztworu pi¬ peracyliny sodu i liofilizowano do otrzymania 1 g/fiolke. Nastepnie fiolki rozcienczano jak powy¬ zej i przeprowadzono takie same badania. Wyniki •5 przedstawiono w Tablicy II.W oparciu o duze zwiekszenie czasu rozpuszcza¬ nia i gestosci i duze zmniejszenie czasu napelnia¬ nia strzykawki w zakresie stezen 400 i 500 mg/ml w Przykladach I i II, stwierdzono, ze 400 mg/ml jest 10 najwyzszym praktycznym stezeniem stosowanym do odtworzenia.Przyklad III. Zaleznosc stezenia cieczy napel¬ niany i czasu odtwarzania.Sporzadzono roztwory piperacyliny sodu w czte- 15 rech róznych stezeniach 2G0, 166,7, 142,9 i 125 mg/ml przez rozcienczenie woda. Odpowiednia iloscia kaz¬ dej cieczy napelniono fiolki tak, aby kazda zawie¬ rala 1 gram piperacyliny sodu. Przygotowano 4 fiolki, które nastepnie liofilizowano. Po liofilizacji7 130 564 8 kazdy 1 g-owy placek odtworzono 1,8 ml wody do koncowej objetosci 2,5 ml o stezeniu roztworu 400 mg/ml. Mierzono czas odtwarzania i wyniki przedstawiono w Tablicy III.Przyklad IV. W Tablicy IV- przedstawiono ilosc roztworu o stezeniu 125 mg/ml konieczna do otrzymania liofilizowanego produktu, który po od¬ tworzeniu bedzie mial koncowe stezenie 400 mg/ml.Kazdy gram piperacyliny sodu zajmuje miejsce 0,7 g wody. Stezenie koncowe uwzglednia nadwyz¬ ke dla kompensowania nieszczelnosci strzykawki i produkt pozostaje we fiolce.Zastrzezenie patentowe Sposób wytwarzania jednostkowej farmaceutycz- 5 nej dawki do podawania pozajelitowego zawiera¬ jacej piperacyline sodu obejmujacy przygotowanie roztworu piperacyliny sodu w wodzie, napelnienie tym roztworem pojemnika do wymaganej ilosci i liofilizacje, znamienny tym, ze roztwór pipera¬ cyliny sodu w wodzie przygotowuje sie w stezeniu od 100 mg/ml do 135 mg/ml, korzystnie 125 mg/ml. 10 ZGK 1761/1131/5 — 85 egz.Cena 100 zl PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PLThe invention relates to a method for preparing a unit dose for parenteral administration containing the sodium salt of 6-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, hereinafter referred to as piperacillin sodium. This salt is described in U.S. Patent No. 4,112,090, which demonstrates its use as an antibacterial agent. The conventional method for preparing a lyophilized dosage form for parenteral administration involves preparing a 200 mg/ml aqueous solution of the penicillin derivative, filling this solution into ampoules at a concentration of 5 ml per ampoule, and then freeze-drying the contents of the ampoules. The dried cake is equivalent to one gram of the penicillin derivative. When a physician prepares to administer the drug, the vial is reconstituted with 3.3 ml of water or other suitable diluent. The penicillin derivative takes up 0.7 ml of diluent per gram of derivative. The final product is therefore 4.0 ml of reconstituted penicillin derivative at a concentration of 250 mg/ml. The physician then withdraws the appropriate amount of solution from the vial into a syringe and administers the appropriate dose to the patient. A difficulty with using this parenteral formulation is that the physician must administer 4 ml of solution per 1 gram dose. Piperacillin, like many penicillin derivatives, is 10, 15, 20, 25, 30 l/min and therefore causes pain upon intramuscular injection. Furthermore, the dose limit for injection into the arm is approximately 2 ml, as the musculature usually cannot tolerate larger interstitial volumes. Therefore, a 4 ml dose necessitates less convenient injection into the buttocks. Even when injected into the buttocks, the large dose of 4 ml increases the drug's dissolution time. The aim of the invention is to develop a parenteral unit dose form of piperacillin sodium that reduces the injection volume compared to the known dose by providing a higher final product concentration. The difficulty in producing a concentrated reconstituted lyophilized drug formulation is that as the final product concentration increases, the reconstitution time also increases. For a final product concentration of 400 mg/ml, the reconstitution time is several minutes with constant shaking. The time required to reconstitute such products has led to a discouragement in their use, resulting in the use of more dilute preparations with all their disadvantages described above. Another object of the invention is to prepare a lyophilized parenteral dosage form of piperacillin sodium of higher concentration, in which the final product is more easily reconstituted. The parenteral dosage unit obtained by the method of the invention comprises a free-flowing, fluffy, porous cake of lyophilized sodium salt of 6-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-3 ...-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-(2-)4-ethyl-2,3-dioxo-1-piperazinecarboxamido) -4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, called piperacillin sodium. The term "porous cake" means a lyophilized cake which occupies a larger volume than a "standard cake". According to the invention, a method for preparing a unit pharmaceutical dosage for parenteral administration containing piperacillin sodium comprises preparing a solution of piperacillin sodium in water, filling this solution into a container to the required quantity and lyophilizing it, wherein the characteristic feature is that the solution of piperacillin sodium in water is prepared in a concentration of 100 mg/ml to 135 mg/ml, preferably 125 mg/ml. In a specific example, the implementation of the claimed solution is as follows: piperacillin sodium is dissolved in water to a concentration of 126 mg/ml. Eight ml of this solution is filled into a vial, to a total of 1 g of piperacillin sodium per vial. Vials are used because they tolerate lyophilization well and are suitable for closure with suitable stoppers, which allow withdrawal of the contents with a syringe. The piperacillin sodium is then frozen and lyophilized in the vials according to a known standard process. During lyophilization, the freeze-dried cake retains the volume of the liquid dose and forms a crystalline, freeze-dried mass with a directional structure, sealed under vacuum. Because the volume of liquid poured is 8 ml, the lyophilized cake is much larger and looser ("porous cake") than the 5 ml cake obtained traditionally, the lyophilized vials are sealed with suitable stoppers. When the physician prepares to administer the drug, the lyophilized cake is reconstituted with 2.5 ml of a suitable diluent. Examples of suitable diluents are water or lidocaine hydrochloride, a local anesthetic that can be added to counteract pain on injection caused by the hypertonic properties of piperacillin. The time required to reconstitute 1 g of lyophilized piperacillin sodium is approximately 35 seconds upon shaking. The final product contains 2.5 ml of a 400 mg/ml solution of piperacillin sodium and an injection dose of 2.5 ml/g as opposed to the previous dose of 4 ml/g. The process described above can be modified to produce a larger or smaller amount of the final product by proportionally increasing or decreasing the amount of 125 mg/ml liquid introduced into the vial prior to lyophilization, and by proportionally increasing or decreasing the amount of diluent required to reconstitute the final product with a final concentration of 400 mg/ml. The process described above can also be modified to use a fill liquid with a concentration higher or lower than 125 mg/ml, although with less success. Higher liquid concentrations increase the density of the lyophilized cake and also increase the reconstitution time required to dissolve piperacillin to a concentration of 400 mg/ml, but not by much. For example, increasing the fill liquid concentration by 15% increases the reconstitution time by more than 100%. (See Example III). Alternatively, lower liquid concentrations can be used, but lower liquid concentrations result in a larger volume of liquid required to obtain a given amount of lyophilized drug and require a larger lyophilization vial. If a more dilute liquid is used, a very large vial is required to fill the proportionally larger volume of liquid and the final product when reconstituted to a concentration of 400 mg/ml will occupy only a relatively small fraction of the total volume of the vial. Practically, the concentration of the liquid should be in the range of 100-135 mg/ml, preferably about 125 mg/ml. The subject of the invention is explained in more detail in the examples which do not limit its scope. Example I. Determination of the optimal final concentration of the product - 2 g/vial. 6-[2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-acid sodium salt. Table I Sample 1 1 % a 4 Amount ml of water to be reconstituted 8.6 6.6 3.6 2.6 a | 1.93. Final Volume ml 10 8 5 4 3.33 Final concentration in mg/ml 200 200 400 00 600 | Mean dissolution time min 0.5 0.5 2.0 5.75 25—30 pH 5.87 5.95 6.09 6.16 6^27 Density 1.0.72 1.090 1.141 1.173 1.206 Viscosity cp 2.6 3.8 1$.2 65 314 | Syringe filling time 26 trials good good sufficient weak weak | 21 trials good good good 1 sufficient 1 1 weak 1 Each gram of piperacillin sodium takes up 0.7 ml of water Time test Syringe filling time: good 5-15 seconds to draw up 1 ml sufficient 20-30 seconds to draw up 1 ml weak 1 minute to draw up 1 ml 5 130 564 6-carboxylic acid was dissolved in water to a concentration of 200 mg/ml. 10 ml of this solution was filled into each of five vials and lyophilized by standard methods. Each of these lyophilized cakes was then reconstituted with various amounts of water to obtain a series of final concentrations of piperacillin sodium, taking into account that each gram of piperacillin sodium takes up the space of 0.7 ml of water. The pH, density, and viscosity of these products were tested by standard methods. Dissolution time was measured by shaking the vials containing the lyophilized The cake and water added for reconstitution were measured and the time required for piperacillin sodium to go into solution was measured. The time required to draw 1 ml of the final product from the vial into the syringe was also determined. The results are summarized in Table I. Example II. Determination of the optimal final product concentration — 1 g/vial. The method described in Example I was used to fill Table II Sample V 2 3 4 and 5 • Amount ml of water to be reconstituted 4.3 3.3 1.8 1.3 0.97 Final volume ml 5 4 2.5 2.0 1.67 Final concentration in mg/ml 200 250 400 500 600 Mean dissolution time min 0.75 0.75 2.75 8.5 25—30 PH 5.83 5.92 6.0^ 6.16 6.26 Density 1.073 1.090 1.141 1.175 1.208 Viscosity cp 2.6 3.8 16.2 65 317 Syringe filling time 26 tests good good sufficient weak weak 21 tests good good good sufficient weak | Each ml of piperacillin sodium takes up 0.7 ml of water Syringe filling time test: good 5—15 seconds to draw up 1 ml sufficient 20—30 seconds to draw up 1 ml weak 1 minute to draw up 1 ml Table III Sample and 2 1 3 1 4 Filling concentration mg/ml 200 166.7 142.9 125 Amount ml in vial 5 6 7 8 Reconstitution Amount ml of water 1.8 1.8 1.8 1.8 Final concentration mg/ml 400 400 400 400 Average reconstitution time 1 min 42 sec 1 min 16 sec 36 sec 15 sec [ Each gram of piperacillin sodium takes up 0.7 ml of water Table IV Vial designation 1 2 3 4 6 Amount ml of solution with a concentration of 125 mg/ml 8.64 17.28 25.92 34.24 50.56 | Amount mg in vial iiiii Amount ml to be reconstituted to 400 mg/ml 2.0 4.0 6.0 7.8 11.6 Concentration Final in mg/ml 400 400 400 404 400 1 Each of five vials of 5 ml of a 200 mg/ml piperacillin sodium solution was lyophilized to obtain 1 g/vial. The vials were then diluted as above and the same tests were performed. The results are shown in Table II. Based on the large increases in dissolution time and density and the large decreases in syringe filling time over the 400 and 500 mg/ml concentration ranges in Examples I and II, 400 mg/ml was found to be the highest practical concentration used for reconstitution. Example III. Relationship of Filling Liquid Concentration to Reconstitution Time. Piperacillin sodium solutions were prepared at four different concentrations. 200, 166.7, 142.9, and 125 mg/ml by dilution with water. Appropriate amounts of each liquid were filled into vials so that each contained 1 gram of piperacillin sodium. Four vials were prepared and then lyophilized. After lyophilization, each 1 g cake was reconstituted with 1.8 ml of water to a final volume of 2.5 ml with a solution concentration of 400 mg/ml. The reconstitution time was measured and the results are presented in Table III. Example IV. Table IV shows the amount of 125 mg/ml solution necessary to obtain a lyophilized product that will have a final concentration of 400 mg/ml after reconstitution. Each gram of piperacillin sodium takes the place of 0.7 g of water. Final concentration includes an overfill to compensate for syringe leakage and the product remains in the vial. Patent claim: A method for manufacturing a unit pharmaceutical dose for parenteral administration containing piperacillin sodium, comprising preparing a solution of piperacillin sodium in water, filling a container with this solution to the required quantity and lyophilizing it, characterized in that the solution of piperacillin sodium in water is prepared in a concentration of 100 mg/ml to 135 mg/ml, preferably 125 mg/ml. 10 ZGK 1761/1131/5 — 85 copies. Price PLN 100. PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL PL

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US6207661B1 (en) 1999-02-22 2001-03-27 Baxter International Inc. Premixed formulation of piperacillin sodium and tazobactam sodium injection
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ITMI20051630A1 (en) * 2005-09-02 2007-03-03 Acs Dobfar Spa INJECTABLE STERILE PHARMACEUTICAL FORMULATION CONTAINING AT LEAST TWO ACTIVE PRINCIPLES
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IL47168A (en) * 1974-05-09 1979-07-25 Toyama Chemical Co Ltd Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same
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