medroxyprogesterone

Also known as 17α-hydroxy-6α-methylprogesterone

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

Chemical data

Formula: C22H32O3
Molecular weight: 344.5 g/mol
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
SMILES: C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)O)C)[C@@]4(C1=CC(=O)CC4)C
InChIKey: FRQMUZJSZHZSGN-HBNHAYAOSA-N
XLogP: 3.5
Polar surface area: 54.4 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

10,012 papers

Endometriosis.Journal of obstetric, gynecologic, and neonatal nursing : JOGNN · 1985
Depot-medroxyprogesterone acetate (DMPA) and cancer: memorandum from a WHO meeting.Bulletin of the World Health Organization · 1986
The effect of depot-medroxyprogesterone acetate on the fetus and nursing infant: a review.Contraception · 1981
Premenstrual syndrome.The Journal of clinical endocrinology and metabolism · 1991
Medroxyprogesterone acetate and homozygous sickle-cell disease.Lancet (London, England) · 1982

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Wikidata facts

Subclass of: steroid
Mass: 344.235145

Show 9 more facts

canonical SMILES: CC1CC2C(CCC3(C2CCC3(C(=O)C)O)C)C4(C1=CC(=O)CC4)C
chemical formula: C₂₂H₃₂O₃
isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@@H]2[C@@]4(C)CCC(=O)C=C14
NCI Thesaurus ID: C629
medical condition treated: endometriosis
Commons category: Medroxyprogesterone
stylized name: medroxyPROGESTERone
defined daily dose: 7
legal status (medicine): boxed warning

Sources (7)

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Encyclopedic overview

6 sections

Contents

Pharmacology
Pharmacodynamics
Chemistry
Society and culture
Generic names
References

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

Excerpted from Wikipedia’s “medroxyprogesterone” article, available under the CC BY-SA 4.0 licence.

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