Medroxyprogesterone

Medroxyprogesterone
Clinical data
Pregnancy; category	X;
ATC code	None;
Legal status
Legal status	US: WARNING;
Identifiers
	IUPAC name (6α)-17-hydroxy-6-methylpregn-4-ene-3,20-dione;
CAS Number	520-85-4;
PubChem CID	1063110631;
ChemSpider	10185;
CompTox Dashboard (EPA)	DTXSID0036508 ;
ECHA InfoCard	100.007.545
Chemical and physical data
Formula	C22H32O3
Molar mass	344.488 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)C)CC[C@H]3[C@@H]1C[C@@H]2C)C)(C)CC4;
	InChI InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1; Key:FRQMUZJSZHZSGN-HBNHAYAOSA-N;

Medroxyprogesterone (INN, BAN), also known as 17α-hydroxy-6α-methylprogesterone, and abbreviated as MP, is a steroidal progestin drug which was never marketed for use in humans.^[2] An acylated derivative, medroxyprogesterone acetate (MPA), is clinically used as a pharmaceutical medicine.^[3] Compared to MPA, MP is over two orders of magnitude less potent as a progestogen.^[4] As such, MP itself is not used clinically, though it has seen limited use in veterinary medicine under the trade name Controlestril in France.^[5] In addition, it is a metabolite of MPA.^[6]

While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,^[3] what is normally being administered is MPA and not MP.^[7]

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1079. ISBN 978-0-412-46630-4. Retrieved 28 May 2012.
^ ^a ^b "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.
^ Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 638. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.
^ Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". J. Steroid Biochem. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.
^ Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Ann. Surg. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[Macdonald1997-2] F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1079. ISBN 978-0-412-46630-4. Retrieved 28 May 2012.

[Merck-3] "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.

[pmid16784762-4] Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762.

[Index_Nominum_2000:_International_Drug_Directory-5] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 638. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.

[pmid1271819-6] Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". J. Steroid Biochem. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.

[pmid1119869-7] Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Ann. Surg. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.

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See also

References