CA2624788A1 - Improved testosterone gel and method of use - Google Patents

Improved testosterone gel and method of use Download PDF

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Publication number
CA2624788A1
CA2624788A1 CA002624788A CA2624788A CA2624788A1 CA 2624788 A1 CA2624788 A1 CA 2624788A1 CA 002624788 A CA002624788 A CA 002624788A CA 2624788 A CA2624788 A CA 2624788A CA 2624788 A1 CA2624788 A1 CA 2624788A1
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Prior art keywords
testosterone
composition
ethanol
gel
amount
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CA002624788A
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French (fr)
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CA2624788C (en
Inventor
Ramana Malladi
Jodi Miller
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Besins Healthcare Luxembourg SARL
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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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/26—Androgens

Abstract

The present invention relates to an improved transdermal hydroalcoholic testosterone gel formulation that provides, among other things, a desirable pharmacokinetic hormone profile, and methods of use.

Claims (44)

1. A method of treating hypogonadism in a male subject comprising the steps of:
a. providing a hydroalcoholic gel pharmaceutical composition comprising:
i. about 1.15% to about 1.8%(w/w) testosterone;
ii. about 0.6% to about 1.2% (w/w) isopropyl myristate;
iii. about 60% to about 80% (w/w) of an alcohol selected from the group consisting of ethanol and isopropanol;
iv. a sufficient amount of a thickening agent to give the composition a viscosity in excess of about 9000 cps; and v. water;
b. administering a therapeutically effective dose of the composition to an area of skin of the subject;

wherein after applying the composition to the skin of the subject, the composition provides sufficient testosterone to give the subject a blood serum concentration of testosterone of between about 298 and 1043 ng testosterone per dl serum.
2. The method of claim 1, wherein the composition comprises about 67.0% to about 74.0% (w/w) of an alcohol selected from the group consisting of ethanol and isopropanol.
3. The method of claim 1, wherein the composition comprises about 1.15% to about 1.25% (w/w) testosterone.
4. The method of claim 1, wherein the composition comprises about 1.22% (w/w) testosterone.
5. The method of claim 1, wherein the composition comprises about 1.30% to about 1.45% (w/w) testosterone.
6. The method of claim 1, wherein the composition comprises about 1.42% (w/w) testosterone.
7. The method of claim 1, wherein the composition comprises about 1.50% to about 1.70% (w/w) testosterone
8. The method of claim 1, wherein the composition comprises about 1.62% (w/w) testosterone.
9. The method of claim 1, wherein the composition comprises about 0.6% to about 1.4% (w/w) of a thickening agent.
10. The method of claim 1, wherein the thickening agent is formed by combining a precursor polyacrylic acid with a neutralizer in the course of forming the composition.
11. The method of claim 10, wherein the thickening agent is neutralized Carbomer 980.
12. The method of claim 10, wherein the thickening agent is neutralized Carbomer 940.
13. The method of claim 11 or 12, wherein the neutralizer is selected from the group consisting of sodium hydroxide, ammonium hydroxide, potassium hydroxide, arginine, aminomethyl propanol, tetrahydroxypropyl ethylenediarnine, triethanolamine, tromethamine, PEG-15 cocamine, diisopropanolamine, triisopropanolamine and combinations thereof.
14. The method of claim 10, wherein the neutralizer is between about 6.5% and 7.5 % (w/w) 0.1 N NaOH.
15. The method of claim 1, wherein the composition has a viscosity of about 13,000 cps to about 33,000 cps.
16. The method of claim 1, wherein the subject has a pretreatment serum testosterone concentration less than about 300 ng/dl.
17. The method of claim 1, wherein the composition is capable of releasing the testosterone after applying the composition to the skin of a subject at a rate and duration that achieves a circulating serum concentration of testosterone greater than about 300 ng per dl serum.
18. The method of claim 17, wherein the serum concentration of testosterone is greater than about 300 ng per dl serum during a time period beginning about 0.5 hours after administration and ending about 24 hours after administration.
19. The method of claim 18, wherein the serum testosterone concentration is maintained between about 400 and 1050 ng testosterone per dl serum.
20. The method of claim 18, wherein the serum testosterone concentration is maintained between about 200 and 1800 ng testosterone per dl serum.
21. The method of claim 1, wherein an obtained C max is between about 300 and ng/dl.
22. The method of claim 1, wherein the therapeutically effective dose is about 1.0 g to about 10.0 g of the composition.
23. The method of claim 22, wherein the therapeutically effective dose is administered daily.
24. The method of claim 1, wherein the therapeutically effective dose is administered once, twice, or three times daily for at least about 7 days.
25. The method of claim 1, wherein the hydroalcoholic gel pharmaceutical composition comprises the result of combining the following ingredients:
a. about 1.15% to about 1.25% (w/w) testosterone;
b. about 67.0% to about 74.0% (w/w) ethanol;
c. about 0.6% to about 1.4% (w/w) isopropyl myristate;
d. about 0.6% to about 1.4% (w/w) carbomer;
e. about 6.5% to about 7.5% (w/w) 0.1N NaOH; and f. additional water.
26. The method of claim 1, wherein the hydroalcoholic gel pharmaceutical composition comprises the result of combining the following ingredients:
a. about 1.30% to about 1.45% (w/w) testosterone;
b. about 67.0% to about 74.0%(w/w) ethanol;
c. about 0.6% to about 1.4%(w/w) isopropyl myristate;
d. about 0.6% to about 1.4% (w/w) carbomer;
e. about 6.5% to about 7.5% (w/w) 0.1N NaOH; and f. additional water.
27. The method of claim 1, wherein the hydroalcoholic gel pharmaceutical composition comprises the result of combining the following ingredients:
a. about 1.5% to about 1.7% (w/w) testosterone;
b. about 67.0% to about 74.0% (w/w) ethanol;
c. about 0.6% to about 1.4% (w/w) isopropyl myristate;
d. about 0.6% to about 1.4% (w/w) carbomer;
e. about 6.5% to about 7.5% (w/w) 0.1N NaOH; and f. additional water.
28. A method of treating hypogonadism in a male subject comprising the steps of:

a. providing a hydroalcoholic gel pharmaceutical composition comprising the result of combining the following ingredients:
i. about 1.40% to about 1.80% (w/w) testosterone;
ii. about 0.6% to about 1.4% (w/w) isopropyl myristate;
iii. about 67.0% to about 74.0% (w/w) ethanol;
iv. about 0.6% to about 1.4% (w/w) carbomer;
v about 6.5% to about 7.5% (w/w) 0.1N NaOH; and vi. additional water;
b. administering a therapeutically effective dose of the composition to an area of skin of the subject;
wherein after applying the composition to the skin of the subject, the composition provides sufficient testosterone to give the subject a blood serum concentration of testosterone of between about 298 and 1043 ng testosterone per dl serum.
29. The method of claim 28, wherein the composition is administered to the shoulder/upper arm and/or abdomen area of the male subject.
30. The method of claim 28, wherein the composition has a viscosity between about 13,000 cps and 33,000 cps.
31. The method of claim 28, wherein the composition comprises about 1.62%
(w/w) testosterone.
32. The method of claim 28, wherein the therapeutically effective dose is about 1.25 g to about 6.25 g of the composition.
33. The method of claim 32, wherein the therapeutically effective dose delivers about 20.3 mg to about 101.1 mg of testosterone to the skin.
34. The method of claim 33, wherein the therapeutically effective dose is administered daily.
35. The method of claim 33, wherein the therapeutically effective dose is administered once daily for at least 14 days.
36. A hydroalcoholic gel for the transdermal delivery of testosterone to a person comprising:
a. testosterone;
b. isopropyl myristate;
c. ethanol;
d. water; and e. a sufficient amount of a thickening agent to give the gel a viscosity in excess of about 9000 cps;
in amounts such that said gel, when applied to human skin mounted in a Frantz cell in an amount of about 300 mg, provides after 24 hours a CAR ratio in excess of 1 wherein said CAR ratio is the ratio of cumulative testosterone which permeates said skin when said gel is so tested to the cumulative testosterone which permeates skin when a hydroalcoholic gel of similar viscosity comprising wt% testosterone, 0.5 wt% isopropyl myristate and 72.5 wt% ethanol 95% v/v is so tested.
37. The hydroalcoholic gel of claim 36, wherein the CAR ratio is in excess of 1.1.
38. The hydroalcoholic gel of claim 37, wherein the CAR ratio is in excess of 2.
39. The hydroalcoholic gel of claim 36, wherein:
a. the amount of testosterone is between about 1.15% and 1.8% (w/w);
b. the amount of isopropyl myristate is between about 0.6% and 1.2%
(w/w); and c. the amount of ethanol is between about 67.0% and 74.0% (w/w).
40. A hydroalcoholic gel for the transdermal delivery of testosterone to a person comprising:
a. testosterone;

b. isopropyl myristate;
c. ethanol;
d. water; and e. a sufficient amount of a thickening agent to give the gel a viscosity in excess of about 9000 cps;
in amounts such that said gel, when applied to human skin mounted in a Frantz cell in an amount of about 300 mg, provides after 24 hours a flux ratio in excess of 1 wherein said flux ratio is the ratio of flux of testosterone expressed in amount per unit area and per unit time which permeates said skin when said gel is so tested to the flux of testosterone which permeates said skin when a hydroalcoholic gel of similar viscosity comprising 1 wt% testosterone, 0.5 wt% isopropyl myristate, and 72.5 wt% ethanol 95% v/v is so tested wherein the flux is determined in both cases by plotting the testosterone which permeates said skin versus time and taking the slope of the linear portion of the curve.
41. The hydroalcoholic gel of claim 40, wherein the flux ratio is in excess of 1.5.
42. The hydroalcoholic gel of claim 40, wherein:
a. the amount of testosterone is between about 1.15% and 1.8% (w/w);
b. the amount of isopropyl myristate is between about 0.6% and 1.2%
(w/w); and c. the amount of ethanol is between about 67.0% and 74.0% (w/w).
43. A hydroalcoholic gel for the transdermal delivery of testosterone to a person comprising:
a. testosterone;
b. isopropyl myristate;
c. ethanol;
d. water; and e. a sufficient amount of a thickening agent to give the gel a viscosity in excess of about 9000 cps;

in amounts such that said gel, when applied to the skin of a person, causes a significantly greater increase in serum concentration of testosterone than the application of the same amount of a hydroalcoholic gel of similar viscosity comprising 1 wt% testosterone, 0.5 wt% isopropyl myristate, and 72.5 wt%
ethanol 95% v/v.
44. The hydroalcoholic gel of claim 43, wherein:
a. the amount of testosterone is between about 1.0% and 2.0% (w/w);
b. the amount of isopropyl myristate is between about 0.5% and 2.0%
(w/w); and c. the amount of ethanol is between about 67.0% and 74.0% (w/w).
CA2624788A 2005-10-12 2006-10-12 Improved testosterone gel and method of use Active CA2624788C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US72527605P 2005-10-12 2005-10-12
US60/725,276 2005-10-12
PCT/US2006/040481 WO2007044976A2 (en) 2005-10-12 2006-10-12 Improved testosterone gel and method of use

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CA2624788A1 true CA2624788A1 (en) 2007-04-19
CA2624788C CA2624788C (en) 2011-04-19

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JP (2) JP5584415B2 (en)
KR (1) KR101342357B1 (en)
CN (1) CN101287470B (en)
AU (1) AU2006299833B2 (en)
BR (1) BRPI0617294B8 (en)
CA (1) CA2624788C (en)
CY (1) CY1120904T1 (en)
DK (2) DK2450041T3 (en)
EA (1) EA012754B1 (en)
EC (1) ECSP088363A (en)
ES (2) ES2399763T3 (en)
GE (1) GEP20125432B (en)
HK (1) HK1117417A1 (en)
HR (1) HRP20130071T1 (en)
IL (1) IL190522A (en)
LT (1) LT2450041T (en)
MA (1) MA29941B1 (en)
NO (2) NO346660B1 (en)
NZ (1) NZ567056A (en)
PL (2) PL1937276T3 (en)
PT (2) PT2450041T (en)
RS (1) RS52671B (en)
SI (2) SI1937276T1 (en)
TN (1) TNSN08167A1 (en)
TR (1) TR201815853T4 (en)
UA (1) UA87627C2 (en)
WO (1) WO2007044976A2 (en)
ZA (1) ZA200803087B (en)

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