# US 7,608,609 B2 · Pharmaceutical composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,609 B2 - Document ID: US7608609B2 - Status: Granted - Kind: B2 - Application number: 12/359,183 - Filed: 2009-01-23 - Published: 2009-05-07 - Granted: 2009-10-27 - Earliest claimed: 2002-04-19 - Assignees: CPEX Pharmaceuticals, Inc. - Inventors: Robert J. Gyurik - Web page: https://patentgrep.com/patent/US7608609B2 ## CPC - A61K 31/568: substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone - A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)} - A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)} - A61K 31/56: Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids - A61K 31/57: substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone - A61K 47/08: containing oxygen, {e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides} - A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers - A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones - A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} - A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) - A61P 3/06: Antihyperlipidemics - A61P 5/24: of the sex hormones - A61P 5/26: Androgens - A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives - A61P 15/08: for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis - A61P 15/10: for impotence - A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease - A61P 21/06: Anabolic agents (androgens A61P5/26) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract A pharmaceutical composition comprising: (A) an androgen; (B) a cyclic enhancer of the type used in the compositions and methods claimed by U.S. Pat. No. 5,023,252 to Hsieh; and (C) a thickening agent; including, for example, a composition in which the cyclic enhancer is a macrocyclic ester or a macrocyclic ketone; the use of the composition to treat a condition, for example, male hypogonadism, in a patient by applying the composition to the membrane of the patient; and a method for making the composition. ## Claims ### Claim 1 A method for maintaining a therapeutically effective concentration of testosterone in the blood serum of a male for treating hypogonadism which comprises transdermally delivering to the male by applying to the skin a composition which is in the form of a topical gel, which has a viscosity of about 2000 to about 6000 cps and a pH of about 4 to about 8, and comprises: (A) about 0.1 to about 5 wt. % of testosterone; (B) about 0.5 to about 15 wt. % of oxacyclohexadecan-2-one; (C) about 1 to about 6 wt. % of a thickening agent; (D) a mixture of solvents which include about 40 wt. % to about 80 wt. % of ethanol. ### Claim 2 (depends on 1) The method of claim 1 further comprising about 0.001 to about 5 wt. % of polyethylene glycol as a crystallization inhibitor. ### Claim 3 (depends on 1) The method of claim 1 wherein ethanol ranges from about 50 wt. % to about 75 wt. %. ### Claim 4 (depends on 3) The method of claim 3 wherein ethanol ranges from about 60 wt. % to about 75 wt. %. ### Claim 5 (depends on 4) The method of claim 4 further comprising propylene glycol. ### Claim 6 (depends on 5) The method of claim 5 further comprising glycerin. ### Claim 7 (depends on 1) The method of claim 1 wherein said composition is maintained on said skin for a period of time sufficient for delivery of the testosterone to the body of the male and is applied to the skin in the form of a unit dose which contains about 1 to about 300 mg of testosterone and such that, following a single application of the unit dose to the skin, the amount of circulating testosterone (AUC0-24) in the blood serum of the male achieved in the 24-hour period following the application is about 100 to about 35,000 ng.h/dL greater than the amount of circulating testosterone (AUC0-24) in the blood serum of the male than would have been achieved in the same 24-hour period had the dose not been administered. ### Claim 8 A method for maintaining a therapeutically effective concentration of testosterone in the blood serum of a male for treating hypogonadism which comprises transdermally delivering to the male by applying to the skin a composition which is in the form of a topical gel, which has a viscosity of about 2000 to about 6000 cps and a pH of about 4 to about 8, and comprises: (A) about 0.1 to about 5 wt. % of testosterone; (B) about 0.5 to about 15 wt. % of oxacyclohexadecan-2-one; (C) about 1 to about 6 wt. % of a thickening agent; (D) a mixture of solvents which include about 40 wt. % to about 80 wt. % of ethanol and (E) about 0.001 to about 5 wt. % of polyethylene glycol as a crystallization inhibitor; wherein said composition is maintained on said skin for a period of time sufficient for delivery of the testosterone to the body of the male and is applied to the skin in the form of a unit dose which contains about 1 to about 300 mg of testosterone and such that, following a single application of the unit dose to the skin, the amount of circulating testosterone (AUC0-24) in the blood serum of the male achieved in the 24-hour period following the application is about 100 to about 35,000 ng.h/dL greater than the amount of circulating testosterone (AUC0-24) in the blood serum of the male than would have been achieved in the same 24-hour period had the dose not been administered. ### Claim 9 (depends on 8) The method of claim 8 wherein ethanol ranges from about 50 wt. % to about 75 wt. %. ### Claim 10 (depends on 9) The method of claim 9 wherein ethanol ranges from about 60 wt. % to about 75 wt. %. ### Claim 11 (depends on 10) The method of claim 10 further comprising propylene glycol. ### Claim 12 (depends on 11) The method of claim 11 further comprising glycerin.