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Haloprogesterone

From Wikipedia, the free encyclopedia
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
  • (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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H28BrFO2
Molar mass411.355 g·mol−1
3D model (JSmol)
  • 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=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 nameProhalone, is aprogestin medication which was previously marketed byAyerst but is now no longer available.[1][2][3]

Chemistry

[edit]
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 asyntheticpregnanesteroid and ahalogenatedderivative ofprogesterone.[1] It is specifically a derivative of17α-bromoprogesterone and is similar structurally tomedrogestone (6-dehydro-6,17α-dimethylprogesterone),medroxyprogesterone acetate (6α-methyl-17α-acetoxyprogesterone), and various other progestins derived from progesterone.[1]

Synthesis

[edit]

Chemical syntheses of haloprogesterone have been published.[4]

History

[edit]

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

Society and culture

[edit]

Generic names

[edit]

Haloprogesterone is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name andUSANTooltip United States Adopted Name.[1][3]

Brand names

[edit]

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

References

[edit]
  1. ^abcdefElks 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. ^abUnited 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
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
Retrieved from "https://en.wikipedia.org/w/index.php?title=Haloprogesterone&oldid=1329018693"
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