Medroxyprogesterone

Source: Wikipedia, the free encyclopedia.
Medroxyprogesterone
Progestin; Progestogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • (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
JSmol)
  • 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=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 (MP), is a

progestin which is not used medically.[2][3][4][5] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.[6] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,[6] and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.[7]

Pharmacology

Pharmacodynamics

Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.[8] Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.[9] In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.[10]

MP and related steroids at the PR (nM)[8]
Compound
Ki
EC50
Tooltip 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

Medroxyprogesterone, also known as 6α-methyl-17α-hydroxyprogesterone or as 6α-methyl-17α-hydroxypregn-4-en-3,20-dione, is a

17α-hydroxyprogesterone with a methyl group at the C6α position.[2][3] 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.[2][3]

Society and culture

Generic names

Medroxyprogesterone is the

INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.[2][3][5]

Brand Name

Meprate 10 Tablets (practo)

References