Hydroxyprogesterone acetate

Hydroxyprogesterone acetate
Clinical data
Trade names	Prodrox
Other names	OHPA; 17α-Hydroxyprogesterone acetate; 17α-Acetoxyprogesterone; Acetoxyprogesterone; 17α-Hydroxypregn-4-ene-3,20-dione 17α-acetate; 17α-Acetoxypregn-4-ene-3,20-dione
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	G03DA03 (WHO) ;
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	302-23-8 ; 17308-02-0;
PubChem CID	10156152;
ChemSpider	8331660;
UNII	L124O66YSI;
KEGG	D08053;
CompTox Dashboard (EPA)	DTXSID90894096 ;
ECHA InfoCard	100.005.564
Chemical and physical data
Formula	C23H32O4
Molar mass	372.505 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](OC(=O)C)(C(=O)C)CC[C@H]3[C@@H]1CC2)C)(C)CC4;
	InChI InChI=1S/C23H32O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h13,18-20H,5-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1; Key:VTHUYJIXSMGYOQ-KOORYGTMSA-N;

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8] It has reportedly also been used in birth control pills.^[9]

OHPA is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.

OHPA was discovered in 1953 and was introduced for medical use in 1956.^[10]^[11]^[12]

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 664–. ISBN 978-1-4757-2085-3.
^ Junkmann K (27 November 2013). "Konstitution und chemische und physikalische Eigenschaften der Gestagene" [Constitution and chemical and physical properties of progestogens]. Die Gestagene (in German). Springer-Verlag. pp. 6, 278. ISBN 978-3-642-99941-3.
^ Cite error: The named reference pmid13475464 was invoked but never defined (see the help page).
^ Lobo R, Crosignani PG, Paoletti R (31 October 2002). Women's Health and Menopause: New Strategies - Improved Quality of Life. Springer Science & Business Media. pp. 91–. ISBN 978-1-4020-7149-2.
^ Stoller JK, Michota FA, Mandell BF (2009). The Cleveland Clinic Foundation Intensive Review of Internal Medicine. Lippincott Williams & Wilkins. pp. 13–. ISBN 978-0-7817-9079-6.
^ Ravina E (11 January 2011). "Hormone Analogs". The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. pp. 194–. ISBN 978-3-527-32669-3.
^ Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 204–. ISBN 978-0-471-89979-2. In 1954, Karl Junkmann of Schering AG reported that the acetylation of the 17-hydroxyl group of ethisterone provided a derivative suitable for formulating in oil for injection intramuscularly as a depot medication.79 There resulted widespread interest in preparing the acetates (and other esters) of various hydroxy-steroids. One such ester, Upjohn's 17-acetoxyprogesterone, provided to be a promising progestogen even though its hydroxy precursor was inactive. Unfortunately, it turned out that no significant prolongation of action was obtained by formulating it in oil. The Upjohn researchers, however, made the unexpected discovery that their acetoxy derivative was orally active, an observation that had been missed by the Schering group, who were primarily interested in the oil solubility of such esters.
^ Cite error: The named reference Upjohn1978 was invoked but never defined (see the help page).
^ Cite error: The named reference RudelKinel1972 was invoked but never defined (see the help page).
^ Cite error: The named reference DavisReprints was invoked but never defined (see the help page).
^ Cite error: The named reference pmid13583817 was invoked but never defined (see the help page).
^ Cite error: The named reference Applezweig1962 was invoked but never defined (see the help page).

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 664–. ISBN 978-1-4757-2085-3.

[Springer2013-2] Junkmann K (27 November 2013). "Konstitution und chemische und physikalische Eigenschaften der Gestagene" [Constitution and chemical and physical properties of progestogens]. Die Gestagene (in German). Springer-Verlag. pp. 6, 278. ISBN 978-3-642-99941-3.

[pmid13475464-3] Cite error: The named reference pmid13475464 was invoked but never defined (see the help page).

[LoboCrosignani2002-4] Lobo R, Crosignani PG, Paoletti R (31 October 2002). Women's Health and Menopause: New Strategies - Improved Quality of Life. Springer Science & Business Media. pp. 91–. ISBN 978-1-4020-7149-2.

[StollerMichota2009-5] Stoller JK, Michota FA, Mandell BF (2009). The Cleveland Clinic Foundation Intensive Review of Internal Medicine. Lippincott Williams & Wilkins. pp. 13–. ISBN 978-0-7817-9079-6.

[Ravina2011-6] Ravina E (11 January 2011). "Hormone Analogs". The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. pp. 194–. ISBN 978-3-527-32669-3.

[Sneader2005-7] Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 204–. ISBN 978-0-471-89979-2. In 1954, Karl Junkmann of Schering AG reported that the acetylation of the 17-hydroxyl group of ethisterone provided a derivative suitable for formulating in oil for injection intramuscularly as a depot medication.79 There resulted widespread interest in preparing the acetates (and other esters) of various hydroxy-steroids. One such ester, Upjohn's 17-acetoxyprogesterone, provided to be a promising progestogen even though its hydroxy precursor was inactive. Unfortunately, it turned out that no significant prolongation of action was obtained by formulating it in oil. The Upjohn researchers, however, made the unexpected discovery that their acetoxy derivative was orally active, an observation that had been missed by the Schering group, who were primarily interested in the oil solubility of such esters.

[Upjohn1978-8] Cite error: The named reference Upjohn1978 was invoked but never defined (see the help page).

[RudelKinel1972-9] Cite error: The named reference RudelKinel1972 was invoked but never defined (see the help page).

[DavisReprints-10] Cite error: The named reference DavisReprints was invoked but never defined (see the help page).

[pmid13583817-11] Cite error: The named reference pmid13583817 was invoked but never defined (see the help page).

[Applezweig1962-12] Cite error: The named reference Applezweig1962 was invoked but never defined (see the help page).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]