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M1629

Sigma-Aldrich

Medroxyprogesterone 17-acetate

≥97% (HPLC)

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
Beilstein/REAXYS Number:
2066112
EC Number:
200-757-9
MDL number:
MFCD00010483
UNSPSC Code:
12352200
PubChem Substance ID:
24896674
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

sterility

non-sterile

assay

≥97% (HPLC)

form

powder

mp

206-207 °C (lit.)

solubility

chloroform: 350 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

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

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

Gene Information

human ... AR(367) , ESR1(2099) , ESRRA(2101) , NR3C1(2908) , NR3C2(4306) , PGR(5241)
rat ... Ar(24208)

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Biochem/physiol Actions

Medroxyprogesterone 17-acetate (MPA) is a synthetic progestin used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis. It is a more potent progestin that the nonacetylated form.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351,H413

Hazard Classifications

Aquatic Chronic 4 - Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Milan Milenkovic et al.
Journal of assisted reproduction and genetics, 28(1), 7-14 (2010-09-16)
To evaluate a slow freezing method for whole ovary cryopreservation by evaluating effects of added cryoprotectant. Sheep ovaries were isolated during surgery, flushed with either Ringer-Acetate or dimethylsulphoxide and cryopreserved by slow freezing. After rapid thawing, viability was assessed by
Liangzhu Li et al.
PloS one, 7(8), e43211-e43211 (2012-08-21)
An effective anti-human immunodeficiency virus-1 (HIV-1) microbicide should exert its action in the absence of causing aberrant activation of topical immunity that will increase the risk of HIV acquisition. In the present study, we demonstrated that the vaginal application of
S Saoncella et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(6), 2805-2810 (1999-03-17)
The assembly of focal adhesions and actin stress fibers by cells plated on fibronectin depends on adhesion-mediated signals involving both integrins and cell-surface heparan sulfate proteoglycans. These two cell-surface receptors interact with different domains of fibronectin. To attempt to identify
Bernhard Payer et al.
Molecular cell, 52(6), 805-818 (2013-11-26)
Transitions between pluripotent and differentiated states are marked by dramatic epigenetic changes. Cellular differentiation is tightly linked to X chromosome inactivation (XCI), whereas reprogramming to induced pluripotent stem cells (iPSCs) is associated with X chromosome reactivation (XCR). XCR reverses the
Ozlem Guzeloglu Kayisli et al.
PloS one, 10(10), e0137855-e0137855 (2015-10-06)
Use of long-acting progestin only contraceptives (LAPCs) offers a discrete and highly effective family planning method. Abnormal uterine bleeding (AUB) is the major side effect of, and cause for, discontinuation of LAPCs. The endometria of LAPC-treated women display abnormally enlarged
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