Medroxyprogesterone

This article is about a synthetic progestin ligand. For the clinically prescribed drug, see medroxyprogesterone 17-acetate.

Medroxyprogesterone
IUPAC name 17-acetyl-17-hydroxy- 6,10,13-trimethyl- 1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS number	520-85-4 Y
PubChem	10631
ChemSpider	10185 Y
UNII	HSU1C9YRES Y
DrugBank	DB00603
KEGG	D08166 N
ChEBI	CHEBI:6715 N
ChEMBL	CHEMBL279067 Y
Jmol-3D images	Image 1
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 Y Key: FRQMUZJSZHZSGN-HBNHAYAOSA-N Y InChI=1/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-HBNHAYAOBM
Properties
Molecular formula	C22H32O3
Molar mass	344.488 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Medroxyprogesterone (MP) is a pregnane that acts as a progestin. An acylated derivative, medroxyprogesterone 17-acetate (MPA) is clinically used as a drug.^[1] Compared to MPA, MP is approximately 100 fold less potent as a progestin.^[2] MP is also a metabolite of MPA.^[3]

While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone 17-acetate,^[1] what is normally being administered is medroxyprogesterone 17-acetate and not medroxyprogesterone.^[4]

Medroxyprogesterone is used to regulate irregular periods in a woman's menstral cycle. This drug is also used with women going through menopause.

See also

• Progestin
• Depo-Provera

References

1. ^ ^{a b} "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. http://www.merck.com/mmpe/lexicomp/medroxyprogesterone.html. Retrieved 2010-07-08. 
2. ^ 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. 
3. ^ 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. 
4. ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1343717.