Haloprogesterone

Haloprogesterone, sold under the brand name Prohalone, is a progestin medication which was previously marketed by Ayerst but is now no longer available.^[1][2][3]

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

Chemistry

See also: List of progestogens

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.^[1] 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.^[1]

Synthesis

Chemical syntheses of haloprogesterone have been published.^[4]

History

Haloprogesterone was synthesized in 1960 and was introduced for medical use by 1961.^[1][5][6]

Society and culture

Generic names

Haloprogesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name and USANTooltip United States Adopted Name.^[1][3]

Brand names

Haloprogesterone was marketed under the brand name Prohalone.^[1]