| Identification | Back Directory | [Name]
Desogestrel | [CAS]
54024-22-5 | [Synonyms]
org2969
Cyclosa
Dicromil
Cerazette
DESTODENE
DESOGESTRAL
DESOGESTREL
Marvelon 150/320
Desogestrel (50 mg)
(17β)-13-Ethyl-11-methylene-19-nor-pregn-4-en-20-yn-17-ol
13-Ethyl-11-methylene-18,19-dinor-17α-4-pregnen-20-yn-17-ol
(17α)-13-Ethyl-11-methylene-18，19-dinorpregn-4-en-20-yn-17-ol
(17R)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
(17a)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
13-ethyl-11-methylene-19-dinorpregn-4-en-20-yn-17-o(17-alpha)-1
13-ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17.alpha.)-
Desogestrel for system suitability, European Pharmacopoeia (EP) Reference Standard
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
(8S,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-Methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol | [EINECS(EC#)]
258-929-4 | [Molecular Formula]
C22H30O | [MDL Number]
MFCD00869346 | [MOL File]
54024-22-5.mol | [Molecular Weight]
310.47 |
| Chemical Properties | Back Directory | [Melting point ]
109-110°C | [alpha ]
D20 +55° (chloroform) | [Boiling point ]
390.62°C (rough estimate) | [density ]
1.0169 (rough estimate) | [refractive index ]
1.5100 (estimate) | [storage temp. ]
-20°C Freezer | [solubility ]
Practically insoluble in water, very soluble in methanol, freely soluble in anhydrous ethanol and in methylene chloride. | [form ]
neat | [pka]
13.07±0.40(Predicted) | [color ]
White to Almost white | [Merck ]
14,2926 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Usage]
A progestogen with low androgenic potency | [Description]
Desogestrel is a synthetic progestogen.1 It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 (Item No. 16672) efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8+ T cells in a dose-dependent manner.2 Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome. | [Originator]
Dicromil,Organol ,W. Germany,1981 | [Uses]
A progestogen with low androgenic potency | [Definition]
ChEBI: Desogestrel is a 17beta-hydroxy steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a progestin and a synthetic oral contraceptive. | [Manufacturing Process]
A solution of 1.0 g of 11,11-methylene-18-methyl-delta4-estren-17-one in 33
ml tetrahydrofuran was added to a potassium-acetylide solution in
tetrahydrofuran.
After 2 hours of stirring at 0°C to 5°C the reaction mixture was acidified with
2N H2SO4and processed further.
By a chromatographic treatment on silica gel and crystallization from pentane
0.7 g of 11,11-methylene-17α-ethynyl-18-methyl-δ4-estren-17β-ol with a
melting point of 109°C to 110°C and an [α]D of +55°C (CHCl3) was obtained. | [Therapeutic Function]
Progestin | [General Description]
Desogestrel, (17α)-13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol, is a 19-nortestosterone analog with good progestin activity. Likethe other progestins, it is orally active and used in combinationwith an estrogen in oral contraceptives. Desogestrel is aprodrug that must be oxidized to the 3-one in vivo to haveprogestational action. CYPs 2C9 and 2C19 have been implicatedin the initial hydroxylation of desogestrel at C3. | [Clinical Use]
Desogestrel also is a prodrug and is rapidly metabolized in the intestinal mucosa and on first pass through the liver to its active metabolite, etonogestrel (3-ketodesogestrel). Following oral administration, the relative bioavailability for desogestrel is approximately 84%. Desogestrel also exhibits high selectivity for the progesterone receptor and low and rogenic activity, and it does not diminish the beneficial effects of estrogen on the lipid profile. |
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