Haloprogesterone

Haloprogesterone

Clinical data
Trade names	Prohalone
Other names	Aloprogesterone; 6α-Fluoro-17α-bromoprogesterone; 6α-Fluoro-17α-bromopregn-4-ene-3,20-dione
Routes of administration	By mouth
Drug class	Progestogen; Progestin
ATC code	None
Identifiers
IUPAC name (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-bromo-6-fluoro-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	3538-57-6
PubChem CID	20056569
ChemSpider	16735842
UNII	803BIX5JG5
KEGG	D04414
ChEMBL	ChEMBL2104328
CompTox Dashboard (EPA)	DTXSID10188868
Chemical and physical data
Formula	C21H28BrFO2
Molar mass	411.355 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)F)C)Br
InChI InChI=1S/C21H28BrFO2/c1-12(24)21(22)9-6-16-14-11-18(23)17-10-13(25)4-7-19(17,2)15(14)5-8-20(16,21)3/h10,14-16,18H,4-9,11H2,1-3H3/t14-,15+,16+,18+,19-,20+,21-/m1/s1 Key:GCCIFDUTISMRTG-TUPTUZDRSA-N

Haloprogesterone, sold under the brand name Prohalone, is a progestin medication which was previously marketed by Ayerst but is now no longer available.

Chemistry

Haloprogesterone, also known as 6α-fluoro-17α-bromoprogesterone or as 6α-fluoro-17α-bromopregn-4-ene-3,20-dione, is a synthetic pregnane steroid and a halogenated derivative of progesterone. It is specifically a derivative of 17α-bromoprogesterone and is similar structurally to medrogestone (6-dehydro-6,17α-dimethylprogesterone), medroxyprogesterone acetate (6α-methyl-17α-acetoxyprogesterone), and various other progestins derived from progesterone.

Synthesis

Chemical syntheses of haloprogesterone have been published.

History

Haloprogesterone was synthesized in 1960 and was introduced for medical use by 1961.

Society and culture

Generic names

Haloprogesterone is the generic name of the drug and its INN and USAN.

Brand names

Haloprogesterone was marketed under the brand name Prohalone.