WO1996014840A1 - Use of menthyl lactate as a pain reliever - Google Patents
Use of menthyl lactate as a pain reliever Download PDFInfo
- Publication number
- WO1996014840A1 WO1996014840A1 PCT/EP1995/004334 EP9504334W WO9614840A1 WO 1996014840 A1 WO1996014840 A1 WO 1996014840A1 EP 9504334 W EP9504334 W EP 9504334W WO 9614840 A1 WO9614840 A1 WO 9614840A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- menthyl lactate
- topical
- composition
- weight
- concentration
- Prior art date
- 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.)
- Ceased
Links
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
Definitions
- the invention relates to the field of analgesics and in particular to topical analgesics.
- the invention further relates to the field of menthol esters.
- Menthol has been used in various topical preparations as a counterirritant, as an aesthetic agent (for its fragrance), and as a plasticizer in denture adhesive compositions. Unfortunately, the aroma of menthol has been a significant hinderance to its use in any meaningful amount other than where its fragrance is desired.
- compositions containing effective counter-irritant amounts of menthol 1.25% to 16% according to the FDA monograph for menthol
- the aroma from menthol can be overpowering.
- menthol esters have been prepared. Most of these esters have disagreeable odors, making them truly unsuitable for use in a topical product. These odors are as disagreeable as, or more so than, menthol itself, especially in amounts which are equimolar with monograph counter-irritant effective amounts of menthol.
- Menthyl lactate is a known compound available e.g. from Haarmann & Reimer GmbH (Germany) under the name FRESCOLAT, Type ML. Two thirds of its molecular weight is attributable to the menthol moiety.
- the manufacturer's product literature indicates that it is a "cooling agent” and that it can be used in body care and cosmetic products in which "long lasting cooling and freshness are desired". According to the manufacturer, menthyl lactate is virtually odorless, not suffering from the "mint note” that is otherwise customary in the case of other menthol derivatives.
- the compound is recommended for use as a flavor in concentrations of 0.005% to 0.2% and in cosmetic and other external products in concentrations ranging from 0.2% to 2.0%.
- menthyl lactate as per the product literature is therefore 2.0% by weight, which would correspond 1.3% by weight of the menthol moiety. Nowhere is there any indication or suggestion that menthyl lactate should be used as a topical pain reliever or at concentrations substantially in excess of those indicated by the product literature.
- An object of the invention is to provide a topical pain reliever for external treatment.
- Another object of the invention is to provide a substantially odor-free composition having topical analgesic properties.
- menthol lactate as the topical pain relieving active agent.
- a topical or mucous membrane suitable composition to the skin of said animal, wherein said composition comprises a topical or mucous membrane pain relieving effective amount of menthyl lactate.
- the invention relates to the use of menthyl lactate (for the manufacture of a topical composition) for achieving topical pain relief.
- the topical composition may either be a pharmaceutical one or a veterinary one, preferably a pharmaceutical one.
- the topical composition is preferably applied to the skin or a mucous membrane of the subject to be treated.
- Menthyl lactate is the lactate ester of menthol and has the structural formula
- the compound is available commercially under the name FRESCOLAT, Type ML from Haarmann & Reimer GmbH (Germany). It can also be readily made by processes known in the art by esterifiying the hydroxy group of menthol with lactic acid.
- menthyl lactate is present in compositions compatible with this use in amounts which range from about 2.0% to about 22% by weight of the total composition, preferably about 6.0% to about 18%, more preferably about 9.0% to about 15%, by weight of the total composition.
- the remainder of the composition may be any suitable topical carrier which is compatible with menthyl lactate.
- the external topical preparations of the invention can be applied to any portion of the skin. However, application to the external genetalia, or the eyelids, or lips is not suggested, recommended, or usually desired.
- Typical external topical carriers and additives suitable for use in the present invention include, but are not limited to, carriers such as lanolin, white petrolatum, propylene glycol (preferably up to about 10%, more preferably about 2% to about 8%), paraffin, an alcohol selected from ethanol and isopropyl alcohol (preferably up to about 30%, more preferably about 10% to about 25%), and water (preferably up to about 80%, more preferably about 45% to about 75%); surfactants such as TWEEN (preferably TWEEN 80) (preferably up to about 2.2%, more preferably about 0.2% to about 2.0%), and glyceryl stearate; thickeners such as accacia, methylcellulose, tragacanth, or a carbomer (preferably carbomer 980 or carbomer 940) (preferably up to about 1.5%, more preferably about 0.5% to about 1.2%); pH adjusters such as triethanolamine (preferably up to 2.4%, more preferably about 0.5% to about 2.0%); and fragrance (preferably up to about 5.5%, more
- compositions for use in the present invention may take any appropriate form for the intended application area including, but not limited to, solutions, suspensions, powders, creams, ointments, impregnated bandages, etc.
- the present invention formulations are applied generally as needed anywhere from once to 6 or more times a day, depending on the degree of relief required and the nature of the pain involved.
- the patient can suitably self regulate the frequency with which the compositions need be applied.
- the Carbomer 980 is dispersed in approximately 90-99% of the water in a mixing tank.
- the propylene glycol is then added to the dispersion.
- a separate tank mix together and dissolve the alcohol, TWEEN 80, fragrance, eucalyptus oil, and menthyl lactate.
- the second mixture is then added to the first mixture with continued mixing.
- a third tank the triethanolamine is dissolved in the remaining water.
- the third mixture is then added to the first mixing tank with continued mixing.
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- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
The use of menthyl lactate for the manufacture of a topical composition for achieving topical pain relief is disclosed. Furthermore, the invention concerns a method of achieving topical pain relief which method comprises topically applying to the external skin of a mammal including man a topical pain relieving effective amount of menthyl lactate.
Description
Use Of Menthyl Lactate As A Pain Reliever
Field Of The Invention
The invention relates to the field of analgesics and in particular to topical analgesics. The invention further relates to the field of menthol esters.
Background Of The Invention
Menthol has been used in various topical preparations as a counterirritant, as an aesthetic agent (for its fragrance), and as a plasticizer in denture adhesive compositions. Unfortunately, the aroma of menthol has been a significant hinderance to its use in any meaningful amount other than where its fragrance is desired.
In compositions containing effective counter-irritant amounts of menthol (1.25% to 16% according to the FDA monograph for menthol), the aroma from menthol can be overpowering.
Various menthol esters have been prepared. Most of these esters have disagreeable odors, making them truly unsuitable for use in a topical product. These odors are as disagreeable as, or more so than, menthol itself, especially in amounts which are equimolar with monograph counter-irritant effective amounts of menthol.
Menthyl lactate is a known compound available e.g. from Haarmann & Reimer GmbH (Germany) under the name FRESCOLAT, Type ML. Two thirds of its molecular weight is attributable to the menthol moiety. The manufacturer's product literature indicates that it is a "cooling agent" and that it can be used in body care and cosmetic products in which "long lasting cooling and freshness are desired". According to the manufacturer, menthyl lactate is virtually odorless, not suffering from the "mint note" that is otherwise customary in the case of other menthol derivatives. The compound is recommended for use as a flavor in concentrations of 0.005% to 0.2% and in cosmetic and other external products in concentrations ranging from 0.2% to 2.0%. The maximum recommended amount of menthyl lactate as per the product literature is therefore 2.0% by weight, which would correspond
1.3% by weight of the menthol moiety. Nowhere is there any indication or suggestion that menthyl lactate should be used as a topical pain reliever or at concentrations substantially in excess of those indicated by the product literature.
Objects Of The Invention
An object of the invention is to provide a topical pain reliever for external treatment.
Another object of the invention is to provide a substantially odor-free composition having topical analgesic properties.
Summary Of The Invention
These and other objects of the invention can be achieved by using menthol lactate as the topical pain relieving active agent.
Detailed Description Of The Invention
The invention concems a method of achieving topical (= external) pain relief, in an animal in need thereof comprising the application of a topical or mucous membrane suitable composition to the skin of said animal, wherein said composition comprises a topical or mucous membrane pain relieving effective amount of menthyl lactate. "Animal" preferably means warm-blooded animal (= mammal) and includes man.
Moreover, the invention relates to the use of menthyl lactate (for the manufacture of a topical composition) for achieving topical pain relief. The topical composition may either be a pharmaceutical one or a veterinary one, preferably a pharmaceutical one. The topical composition is preferably applied to the skin or a mucous membrane of the subject to be treated.
Menthyl lactate is the lactate ester of menthol and has the structural formula
The compound is available commercially under the name FRESCOLAT, Type ML from Haarmann & Reimer GmbH (Germany). It can also be readily made by processes known in the art by esterifiying the hydroxy group of menthol with lactic acid.
For use as a topical pain reliever, menthyl lactate is present in compositions compatible with this use in amounts which range from about 2.0% to about 22% by weight of the total composition, preferably about 6.0% to about 18%, more preferably about 9.0% to about 15%, by weight of the total composition. The remainder of the composition may be any suitable topical carrier which is compatible with menthyl lactate.
The external topical preparations of the invention can be applied to any portion of the skin. However, application to the external genetalia, or the eyelids, or lips is not suggested, recommended, or usually desired.
Typical external topical carriers and additives suitable for use in the present invention include, but are not limited to, carriers such as lanolin, white petrolatum, propylene glycol (preferably up to about 10%, more preferably about 2% to about 8%), paraffin, an alcohol selected from ethanol and isopropyl alcohol (preferably up to about 30%, more preferably about 10% to about 25%), and water (preferably up to about 80%, more preferably about 45% to about 75%); surfactants such as TWEEN (preferably TWEEN 80) (preferably up to about 2.2%, more preferably about 0.2% to about 2.0%), and glyceryl stearate; thickeners such as accacia, methylcellulose, tragacanth, or a carbomer (preferably carbomer 980 or carbomer 940) (preferably up to about 1.5%, more preferably about 0.5% to about 1.2%);
pH adjusters such as triethanolamine (preferably up to 2.4%, more preferably about 0.5% to about 2.0%); and fragrance (preferably up to about 5.5%, more preferably about 0.2% to about 5.0%, most preferably about 0.5% to about 4.0%), especially eucalyptus oil (preferably up to 5.5%, more preferably about 0.2% to about 5.0%), and the like, and mixtures thereof.
The compositions for use in the present invention may take any appropriate form for the intended application area including, but not limited to, solutions, suspensions, powders, creams, ointments, impregnated bandages, etc.
The present invention formulations are applied generally as needed anywhere from once to 6 or more times a day, depending on the degree of relief required and the nature of the pain involved. The patient can suitably self regulate the frequency with which the compositions need be applied.
The following example is intended to exemplify, but not to limit the invention.
Example 1 :
Ingredient Amount
Carbomer 980 0.8%
Purified Water 67.2%
Propylene Glycol 5.0%
Menthyl Lactate 9.0%
Eucalyptus Oil 0.5%
SD 3A Alcohol (= ι ca. 95 Vol% ethanol denatured with ca. , 5 Vol% methanol) 15.0%
TWEEN 80 0.5%
Triethanolamine 1.0%
Fragrance 1.0%
The Carbomer 980 is dispersed in approximately 90-99% of the water in a mixing tank. The propylene glycol is then added to the dispersion. In a separate tank, mix together and
dissolve the alcohol, TWEEN 80, fragrance, eucalyptus oil, and menthyl lactate. The second mixture is then added to the first mixture with continued mixing. In a third tank, the triethanolamine is dissolved in the remaining water. The third mixture is then added to the first mixing tank with continued mixing.
Claims
1. The use of menthyl lactate for the manufacture of a topical composition for achieving topical pain relief.
2. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 2.0% to about 22% by weight of the total composition.
3. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 6.0% to about 18% by weight of the total composition.
4. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 9.0% to about 15% by weight of the total composition.
5. A method of achieving topical pain relief in an animal in need thereof comprising topically applying to the external skin of said animal a topical pain relieving effective amount of menthyl lactate.
6. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 2.0% to about 22% by weight of the total composition.
7. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 6.0% to about 18% by weight of the total composition.
8. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 9.0% to about 15% by weight of the total composition.
9. A topical pharmaceutical composition for achieving topical pain relief consisting essentially of menthyl lactate and at least one topically acceptable carrier.
10. Menthyl lactate for use as a topical pain reliever.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU38708/95A AU3870895A (en) | 1994-11-14 | 1995-11-04 | Use of menthyl lactate as a pain reliever |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33942894A | 1994-11-14 | 1994-11-14 | |
| US08/339,428 | 1994-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996014840A1 true WO1996014840A1 (en) | 1996-05-23 |
Family
ID=23328966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/004334 Ceased WO1996014840A1 (en) | 1994-11-14 | 1995-11-04 | Use of menthyl lactate as a pain reliever |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU3870895A (en) |
| WO (1) | WO1996014840A1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
| EP1250940A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| EP1250941A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| US6972010B2 (en) | 2001-04-17 | 2005-12-06 | The Procter & Gamble Company | Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived |
| US8273367B2 (en) | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| US8282607B2 (en) * | 2003-05-14 | 2012-10-09 | Chattem, Inc. | Sleeve and micro-encapsulated topical analgesic for pain relief |
| JP2012197300A (en) * | 2005-01-04 | 2012-10-18 | Teikoku Pharma Usa Inc | Cooling topical patch preparation |
| EP3108880A1 (en) | 2015-06-26 | 2016-12-28 | Natures Innovation, Inc. | Analgesics based on snake venoms |
| US10543236B2 (en) | 2013-07-26 | 2020-01-28 | Natures Innovation Inc. | Analgesics based on snake venoms |
| JP2022144971A (en) * | 2021-03-19 | 2022-10-03 | 株式会社マンダム | Trpv1 activity inhibitor, and use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608226A1 (en) * | 1976-02-28 | 1977-09-08 | Haarmann & Reimer Gmbh | AGENTS WITH PHYSIOLOGICAL COOLING EFFECT |
-
1995
- 1995-11-04 WO PCT/EP1995/004334 patent/WO1996014840A1/en not_active Ceased
- 1995-11-04 AU AU38708/95A patent/AU3870895A/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608226A1 (en) * | 1976-02-28 | 1977-09-08 | Haarmann & Reimer Gmbh | AGENTS WITH PHYSIOLOGICAL COOLING EFFECT |
Non-Patent Citations (1)
| Title |
|---|
| SAKATA I ET AL: "SYNTHESIS AND PROPERTIES OF MENTHYL GLYCOSIDES", AGRIC BIOL CHEM, 43 (2). 1979. 307-312. * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
| CN100540063C (en) * | 2001-04-17 | 2009-09-16 | 宝洁公司 | Articles comprising mint odor-free cooling agents |
| EP1250941A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| WO2002083192A1 (en) * | 2001-04-17 | 2002-10-24 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| WO2002083191A1 (en) * | 2001-04-17 | 2002-10-24 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| US6972010B2 (en) | 2001-04-17 | 2005-12-06 | The Procter & Gamble Company | Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived |
| EP1250940A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| US8273367B2 (en) | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| US8282607B2 (en) * | 2003-05-14 | 2012-10-09 | Chattem, Inc. | Sleeve and micro-encapsulated topical analgesic for pain relief |
| JP2012197300A (en) * | 2005-01-04 | 2012-10-18 | Teikoku Pharma Usa Inc | Cooling topical patch preparation |
| US10543236B2 (en) | 2013-07-26 | 2020-01-28 | Natures Innovation Inc. | Analgesics based on snake venoms |
| US11090340B2 (en) | 2013-07-26 | 2021-08-17 | Nature's Innovation, Inc. | Analgesics based on snake venoms |
| EP3108880A1 (en) | 2015-06-26 | 2016-12-28 | Natures Innovation, Inc. | Analgesics based on snake venoms |
| JP2022144971A (en) * | 2021-03-19 | 2022-10-03 | 株式会社マンダム | Trpv1 activity inhibitor, and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3870895A (en) | 1996-06-06 |
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