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Merck
CN

286648

Medroxyprogesterone 17-acetate

97%

Synonym(s):

17α-Acetoxy-6α-methylprogesterone, 17α-Hydroxy-6α-methyl-4-pregnene-3,20-dione 17-acetate, 6α-Methyl-17α-acetoxyprogesterone, 6α-Methyl-17α-hydroxyprogesterone acetate

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About This Item

Empirical Formula (Hill Notation):
C24H34O4
CAS Number:
71-58-9
Molecular Weight:
386.52
EC Number:
200-757-9
UNSPSC Code:
12352103
MDL number:
MFCD00010483
Beilstein/REAXYS Number:
2066112

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InChI

1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1

InChI key

PSGAAPLEWMOORI-PEINSRQWSA-N

SMILES string

[H][C@@]12C[C@H](C)C3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@@]4(C)[C@@]2([H])CC[C@]4(OC(C)=O)C(C)=O

assay

97%

optical activity

[α]25/D +58°, c = 1 in chloroform

mp

206-207 °C (lit.)

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Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
06004TN
05605JN
03723KF
26223JO
21317KS

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Wen-Jun Shi et al.
Ecotoxicology and environmental safety, 193, 110371-110371 (2020-03-03)
Medroxyprogesterone acetate (MPA) is a widely used synthetic progestin in contraception pills and hormone replacement therapy. However, its effects on eye growth and development and function were largely unknown. In this study, the transcription of genes in the Notch signaling
Wen-Jun Shi et al.
Aquatic toxicology (Amsterdam, Netherlands), 212, 70-76 (2019-05-12)
Medroxyprogesterone acetate (MPA) is a widely used synthetic progestin and it has been frequently detected in aquatic environments. However, its effects on aquatic organisms remain largely unknown. Here we investigated the chronic effects of MPA on sex differentiation and gonad
Annu A Söderholm et al.
Journal of medicinal chemistry, 49(14), 4261-4268 (2006-07-11)
We report a docking and comparative molecular similarity indices analysis (CoMSIA) study of progesterone receptor (PR) ligands with an emphasis on nonsteroids including tanaproget. The ligand alignment generation, a critical part of model building, comprised two stages. First, thorough conformational
Bijan Pedram et al.
Journal of medicinal chemistry, 51(13), 3696-3699 (2008-06-17)
The progesterone receptor plays an important role in the female reproductive system. Here we describe the discovery of a new selective progesterone receptor modulator (SPRM). In rats, the lead compound, 7,9-difluoro-5-(3-methylcyclohex-2-enyl)-2,2,4-trimethyl-1,2-dihydrochromeno[3,4- f]quinoline ( 5c), inhibited ovulation and showed full efficacy
Puwen Zhang et al.
Bioorganic & medicinal chemistry, 15(20), 6556-6564 (2007-08-08)
We have recently discovered 5-(3-cyclopentyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (14) as a potent, selective, and orally active non-steroidal progesterone receptor (PR) agonist. Compound 14 and its analog 13 possessed sub-nanomolar in vitro potency (EC(50) 0.1-0.5nM) in the T47D alkaline phosphatase assay, similar to that
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