Medroxyprogesterone

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see medroxyprogesterone acetate.

Medroxyprogesterone (MP), is a progestin which is not used medically.^[1][2][3][4] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.^[5] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,^[5] and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.^[6]

Medroxyprogesterone

Clinical data
Other names	MP; Methylhydroxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione
Drug class	Progestin; Progestogen
ATC code	None
Identifiers
IUPAC name (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	520-85-4
PubChem CID	10631
ChemSpider	10185
UNII	HSU1C9YRES
CompTox Dashboard (EPA)	DTXSID0036508
ECHA InfoCard	100.007.545
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 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

Pharmacology

Pharmacodynamics

Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.^[7] Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.^[8] In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.^[9]

MP and related steroids at the PR (nM)^[7]

Compound	Ki	EC50Tooltip Half-maximal effective concentrationa	EC50b
Progesterone	4.3	0.9	25
Medroxyprogesterone	241	47	32
Medroxyprogesterone acetate	1.2	0.6	0.15
Values are nM. a = Coactivator recruitment. b = Reporter cell line.

Chemistry

See also: List of progestogens

Medroxyprogesterone, also known as 6α-methyl-17α-hydroxyprogesterone or as 6α-methyl-17α-hydroxypregn-4-en-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone.^[1][2] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.^[1][2] The generic name of medroxyprogesterone is a contraction of 6α-methyl-17α-hydroxyprogesterone. It is closely related to medrogestone as well as other unesterified 17α-hydroxyprogesterone derivatives such as chlormadinone, cyproterone, and megestrol.^[1][2]

Society and culture

Generic names

Medroxyprogesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.^[1][2][4]

Brand Name

Meprate 10 Tablets (practo)