Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07J—STEROIDS
  • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07J—STEROIDS
  • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
  • C07J1/0003—Androstane derivatives
  • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
  • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified

Definitions

• the antiandrogenic activity of the steroid of this invention is remarkable because the corresponding 16- monomethyl steroid, a compound prepared by the instant inventor a number of years ago as disclosed in Example 7 of US. Pat. No. 3,049,555, has the opposite biological effect: it is androgenic.
• the monomethyl steroid also promotes anabolism, a possibly complicating side-effect which the dimethyl steroid of this invention does not share.
• the antiandrogenic utility of l7,B-hydroxy-16,l6- dimethylestr-4-en-3-one is evident from the results of a test for its capacity to inhibit the testosteronestimulated growth of seminal vesicle and prostate glands in castrated immature male rats.
• the procedure is as follows: 20 male Charles River rats are castrated at 22 days of age and separated into 2 equal groups such that for each animal in each group there is a littermate in the other. When the rats areabout 36 days old, an implant consisting of a mixture of 8 mg. of testosterone, 8 mg. of Carbowax (polyethylene glycol), and 16 mg.
• Flexo Wax C Light non-crystalline hydrocarbon wax melting at 6064 C.
• the compound to be tested dissolved or suspended in sesame oil, corn oil, or other physiologically inert vehicle is administered subcutaneously to each animal in one group at a dose of 10 mg. per kg. .daily for 24 successive days.
• the quantity of vehicle is such that a l-gm. rat receives approximately 0.1 ml. at the beginning of the test and with increasing body weight approximately 0.2 ml. at the end.
• Each animal in the second group receives concurrent subcutaneous daily injections of vehicle likewise adjusted to body weight, and these animals serve as controls.
• a compound is considered antiandrogenic if the mean weight of the vesicles in the group of nimalaflsatssilhs[@WfihifiiiflifiQflQflY .0 g (101) less than the corresponding weight in the control group and there is a proportionate decrease in the mean prostate weight for treats vis-a-vis controls. l7B-Hydroxyl6,16-dimethylestr-4-en-3-one was active in this test.
• the steroid of this invention can be administered in dosage unit form including, but not necessarily limited to, sterile solutions or suspensions for intramuscular injection, intravaginal or rectal compositions such as suppositories, lozenges for sublingual administration, and salves or lotions (including sprayable solutions or mixtures) for topical application.
• the appropriate dose in any given instance depends upon the nature of the condition treated and its severity, the route of administration, the species of mammal involved and its size and individual idiosyncrasies, etc. In general, and insofar as consistent with such factors,
• daily parenteral dosages of from 1 to about 5 mg. per
• EXAMPLE 1 Preparation of sterile solution A sterile solution containing mg. per ml. of 173- hydroxy-l6,16-dimethylestr-4-en-3-one is prepared by dissolving 10 gm. thereof in 50 ml. of benzyl alcohol, diluting to 1 l. with polyethylene glycol 400, and then filtering to remove microorganisms.
• EXAMPLE 2 Preparation of sterile suspension A sterile suspension is prepared by mixing 100 gm. of sorbitol with 30 mg. of polyethylene glycol 400 and 4 mg. of benzyl alcohol, whereupon sterilization is effected by filtration and to the filtrate is added 250 mg.
• EXAMPLE 4 EXAMPLE 5 Preparation of a salve A mixture of 15 parts of stearyl alcohol, 4 parts of cetyl alcohol, and 20 parts of polyethylene glycol 400 is melted, whereupon 10 parts of 17B-hydroxy-l6,16-
• compositions adapted to topical application comprise fatty alcohols, fatty acids, liquid petrolatum, glycerol monostearate, glycerol, propylene glycol and other polyalcohols, ethylene glycol polymers, surfactants, vegetable oils, fats, esters of fatty acids and fatty alcohols, water, and hydrous or anhydrous emulsion bases or gels.

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Publications (1)

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Cited By (5)

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Citations (2)

• 1973
  • 1973-05-29 US US00364340A patent/US3853926A/en not_active Expired - Lifetime
• 1974
  • 1974-05-22 ZA ZA00743304A patent/ZA743304B/xx unknown
  • 1974-05-28 NO NO741929A patent/NO140104C/no unknown
  • 1974-05-28 NL NL7407122A patent/NL7407122A/xx not_active Application Discontinuation
  • 1974-05-28 AT AT438674A patent/AT333990B/de not_active IP Right Cessation
  • 1974-05-28 ES ES426711A patent/ES426711A1/es not_active Expired
  • 1974-05-28 BE BE144827A patent/BE815626A/xx unknown
  • 1974-05-28 DE DE19742425822 patent/DE2425822A1/de not_active Withdrawn
  • 1974-05-28 CA CA200,995A patent/CA1033716A/en not_active Expired
  • 1974-05-28 DK DK289274A patent/DK132328C/da active
  • 1974-05-28 JP JP49060202A patent/JPS5019745A/ja active Pending
  • 1974-05-28 IE IE1123/74A patent/IE39292B1/xx unknown
  • 1974-05-28 PH PH15876A patent/PH10428A/en unknown
  • 1974-05-28 FI FI1632/74A patent/FI53218C/fi active
  • 1974-05-28 IL IL44903A patent/IL44903A/en unknown
  • 1974-05-28 SE SE7407031A patent/SE401835B/xx unknown
  • 1974-05-28 HU HUSE1731A patent/HU168555B/hu unknown
  • 1974-05-28 FR FR7418471A patent/FR2231383B1/fr not_active Expired
  • 1974-05-28 GB GB2351174A patent/GB1416839A/en not_active Expired
  • 1974-05-29 AR AR253974A patent/AR199619A1/es active
  • 1974-05-29 CH CH735574A patent/CH609705A5/xx not_active IP Right Cessation

Patent Citations (2)

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