Dydrogesterone

Dydrogesterone
Clinical data
Trade names	Duphaston, others
Other names	Isopregnenone; Dehydroprogesterone; Didrogesteron; 6-Dehydroretroprogesterone; 9β,10α-Pregna-4,6-diene-3,20-dione; NSC-92336
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
Drug class	Progestogen; Progestin
ATC code	G03DB01 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	28%
Protein binding	? (probably to albumin)
Metabolism	Hepatic: AKR1C1, AKR1C3, CYP3A4
Metabolites	20α-DHDTooltip 20α-Dihydrodydrogesterone (exclusively via AKR1C1 and AKRC13)
Elimination half-life	Parent: 5–7 hours; Metabolite: 14–17 hours
Excretion	Urine
Identifiers
	IUPAC name (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	152-62-5 ;
PubChem CID	9051;
DrugBank	DB00378 ;
ChemSpider	8699 ;
UNII	90I02KLE8K;
KEGG	D01217 ;
ChEBI	CHEBI:31527 ;
CompTox Dashboard (EPA)	DTXSID1022974 ;
ECHA InfoCard	100.005.280
Chemical and physical data
Formula	C21H28O2
Molar mass	312.453 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	144 °C (291 °F)
Boiling point	463 °C (865 °F)
Solubility in water	Insoluble mg/mL (20 °C)
	SMILES O=C4\C=C3\C=C/[C@@H]1[C@@H](CC[C@@]2([C@@H](C(=O)C)CC[C@@H]12)C)[C@]3(C)CC4;
	InChI InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1 ; Key:JGMOKGBVKVMRFX-HQZYFCCVSA-N ;
	(verify)

Dydrogesterone, sold under the brand name Duphaston among others, is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy. It is taken by mouth.

Side effects of dydrogesterone include menstrual irregularities, headache, nausea, breast tenderness, and others. Dydrogesterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. The medication is an atypical progestogen and does not inhibit ovulation. It has weak antimineralocorticoid activity and no other important hormonal activity.

Dydrogesterone was developed in the 1950s and introduced for medical use in 1961. It is available widely throughout Europe, no longer available in the United Kingdom, since 2008 and is also marketed in Australia and elsewhere in the world. The medication was previously available in the United States, but it has been discontinued in that country.