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Desogestrel

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Desogestrel Basic information
Product Name:Desogestrel
Synonyms:13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(17α)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-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;(17R)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol;(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;Desogestrel (50 mg);DESTODENE;Desogestrel for system suitability, European Pharmacopoeia (EP) Reference Standard
CAS:54024-22-5
MF:C22H30O
MW:310.47
EINECS:258-929-4
Product Categories:Hormone Drugs;Steroid and Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;API
Mol File:54024-22-5.mol
Desogestrel Structure
Desogestrel Chemical Properties
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.
pka13.07±0.40(Predicted)
form Solid
color White to Almost white
Merck 14,2926
Major Applicationpharmaceutical (small molecule)
InChIInChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3
InChIKeyRPLCPCMSCLEKRS-UHFFFAOYSA-N
SMILESC1C2C(CCC3C2C(=C)CC2(CC)C3CCC2(C#C)O)=CCC1
Safety Information
Safety Statements 24/25
RIDADR UN 3077 9 / PGIII
WGK Germany 3
RTECS JF7975000
HS Code 29372390
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAquatic Acute 1
Aquatic Chronic 1
Repr. 1B
Hazardous Substances Data54024-22-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Desogestrel English
Desogestrel Usage And Synthesis
DescriptionDesogestrel is a synthetic progestogen. It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8+ T cells in a dose-dependent manner. Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome.
Chemical PropertiesWhite Solid
OriginatorDicromil,Organol ,W. Germany,1981
UsesA progestogen with low androgenic potency
DefinitionChEBI: 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 ProcessA 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 FunctionProgestin
General DescriptionDesogestrel, (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 UseDesogestrel 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.
References[1] J VAN DER VIES  J de V. Endocrinological studies with desogestrel.[J]. Arzneimittel-Forschung-Drug Research, 1983, 33 2: 231-236.
[2] MARGIT FRHLICH. In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins[J]. Biochemical pharmacology, 2004, 68 12: Pages 2409-2416. DOI: 10.1016/j.bcp.2004.08.026
Desogestrel Preparation Products And Raw materials
Raw materialsAmmonia-->Sodium borohydride-->1,2-Ethanedithiol-->ESTRONE(RG)-->Sulfuric acid
Preparation ProductsEtonogestrel
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