Medroxyprogesterone

Medroxyprogesterone

Clinical data
Pregnancy category	X
ATC code	None
Identifiers
IUPAC name (6α)-17-hydroxy-6-methylpregn-4-ene-3,20-dione
CAS Number	520-85-4
PubChem (CID)	1063110631
ChemSpider	10185
Chemical and physical data
Formula	C22H32O3
Molar mass	344.488 g/mol
3D model (Jmol)	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.^[1] An acylated derivative, medroxyprogesterone acetate (MPA), is clinically used as a pharmaceutical medicine.^[2] Compared to MPA, MP is over two orders of magnitude less potent as a progestogen.^[3] As such, MP itself is not used clinically, though it has seen limited use in veterinary medicine under the trade name Controlestril in France.^[4] In addition, it is a metabolite of MPA.^[5]

While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,^[2] what is normally being administered is MPA and not MP.^[6]

See also

• Medroxyprogesterone acetate
• Megestrol
• Megestrol acetate
• 17-Hydroxyprogesterone

References

1. F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1079. ISBN 978-0-412-46630-4. Retrieved 28 May 2012.
2. "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.
3. 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.
4. Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 638. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.
5. 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.
6. 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.