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.[1][2][3]

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.[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 INN and USAN.[1][3]

Brand names

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

References

Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 620–. ISBN 978-1-4757-2085-3.
American Pharmaceutical Association (1976). APhA drug names: an index of drug names. American Pharmaceutical Association.
United States Adopted Names (USAN). United States Pharmacopeial Convention. 1968. p. 715.
Die Gestagene. Springer-Verlag. 27 November 2013. pp. 9–10. ISBN 978-3-642-99941-3.
Official Gazette of the United States Patent Office. The Office. 1961. p. 74.
The Journal of New Drugs. 1962. p. 127.

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 620–. ISBN 978-1-4757-2085-3.

[Association1976-2] American Pharmaceutical Association (1976). APhA drug names: an index of drug names. American Pharmaceutical Association.

[USPC1968-3] United States Adopted Names (USAN). United States Pharmacopeial Convention. 1968. p. 715.

[Springer2013-4] Die Gestagene. Springer-Verlag. 27 November 2013. pp. 9–10. ISBN 978-3-642-99941-3.

[TheOffice1961-5] Official Gazette of the United States Patent Office. The Office. 1961. p. 74.

[JND1962-6] The Journal of New Drugs. 1962. p. 127.