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Haloprogesterone

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Chemical compound Pharmaceutical compound
Haloprogesterone
Clinical data
Trade namesProhalone
Other namesAloprogesterone; 6α-Fluoro-17α-bromoprogesterone; 6α-Fluoro-17α-bromopregn-4-ene-3,20-dione
Routes of
administration		By mouth
Drug classProgestogen; 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-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28BrFO2
Molar mass411.355 g·mol
3D model (JSmol)
SMILES
  • CC(=O)1(CC21(CC32C(C4=CC(=O)CC34C)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

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. 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 INNTooltip International Nonproprietary Name and USANTooltip United States Adopted Name.

Brand names

Haloprogesterone was marketed under the brand name Prohalone.

References

  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.
  2. American Pharmaceutical Association (1976). APhA drug names: an index of drug names. American Pharmaceutical Association. ISBN 9780917330094.
  3. ^ United States Adopted Names (USAN). United States Pharmacopeial Convention. 1968. p. 715.
  4. Die Gestagene. Springer-Verlag. 27 November 2013. pp. 9–10. ISBN 978-3-642-99941-3.
  5. Official Gazette of the United States Patent Office. The Office. 1961. p. 74.
  6. The Journal of New Drugs. 1962. p. 127.


Progestogens and antiprogestogens
Progestogens
(and progestins)
PRTooltip Progesterone receptor agonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptor antagonists
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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