Dienogest

Title: Dienogest
CAS Registry Number: 65928-58-7
CAS Name: (17a)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
Additional Names: 17a-cyanomethyl-17b-hydroxy-13b-methylgona-4,9-dien-3-one; 17a-cyanomethyl-17b-hydroxy-4,9-estradien-3-one; dienogestril
Manufacturers' Codes: STS-557
Trademarks: Endometrion (Jenapharm)
Molecular Formula: C20H25NO2
Molecular Weight: 311.42
Percent Composition: C 77.14%, H 8.09%, N 4.50%, O 10.28%
Literature References: Derivative of 19-nortestosterone. Prepn: K. Ponsold et al., DE 2718872; eidem, US 4167517 (1977, 1979 both to VEB Jenapharm); M. Hübner et al., Arzneim.-Forsch. 30, 401 (1980). Structure-activity study: M Hübner, K. Ponsold, Exp. Clin. Endocrinol. 81, 109 (1983). Evaluation of combination with estrogen as oral contraceptive: J. Spona et al., Contraception 56, 185 (1997); as hormone replacement therapy: T. Gräser et al., Maturitas 35, 253 (2000). Review of pharmacology and clinical experience: R. H. Foster, M. I. Wilde, Drugs 56, 825-833 (1998).
Properties: Needles from ethyl acetate + acetonitrile, mp 209-214°. [a]D25 -290° (c = 0.5 in pyridine).
Melting point: mp 209-214°
Optical Rotation: [a]D25 -290° (c = 0.5 in pyridine)
Derivative Type: Mixture with ethinyl estradiol
CAS Registry Number: 170475-05-5
Trademarks: Certostat (Jenapharm); Valette (Jenapharm)
Therap-Cat: Progestogen. In combination with estrogen as oral contraceptive.
Keywords: Progestogen; Contraceptive (Oral).
Diethadione Diethazine Diethofencarb Diethyl Carbitol? Diethyl Ketone

Dienogest
Dienogest.svg
Systematic (IUPAC) name
[(17β)-17-Hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile
Clinical data
Trade names Visanne
AHFS/Drugs.com International Drug Names
Pregnancy cat. B3 (AU)
Legal status Prescription Only (S4) (AU)
Routes Oral
Pharmacokinetic data
Bioavailability 90%[1]
Protein binding 90%[2]
Metabolism Hepatic (CYP3A4-mediated)[3]
Half-life 6-12 hours[4]
Excretion Renal
Identifiers
CAS number 65928-58-7 YesY
ATC code G03DB08
G03AB08 G03FA15 (combinations with estrogen)
PubChem CID 68861
ChemSpider 62093 N
UNII 46M3EV8HHE N
KEGG D03799 YesY
ChEBI CHEBI:70708 N
ChEMBL CHEMBL1201864 N
Synonyms 17-hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile
17α-cyanomethyl-17β-hydroxy-estra-4,9(10)-dien-3-one
Chemical data
Formula C20H25NO2 
Mol. mass 311.42 g/mol[1]
Physical data
Density 1.2 g/cm³
Boiling point 549 °C (1020 °F)
 N (what is this?)  (verify)

Dienogest is an orally-active semisynthetic, steroidal progestogen (or progestin).[5] It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms.[1][6] It is a non-ethinylated progestin which is structurally related to testosterone.[3] Dienogest given in isolation is available for the treatment of endometriosis under the trade name Visanne.