Medroxyprogesterone Acetate

  • CAT Number: A000995
  • CAS Number: 71-58-9
  • Molecular Formula: C24H34O4
  • Molecular Weight: 386.52
  • Purity: ≥95%
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Medroxyprogesterone Acetate, also known as MPA, is a steroidal progestin, a synthetic variant of the steroid hormone progesterone. It is used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis as well as several other indications. MPA is a more potent derivative of its parent compound medroxyprogesterone (MP). While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, what is almost always being referred to is MPA and not MP It is on the World Health Organization/’s List of Essential Medicines, the most important medication needed in a basic health system.

Catalog Number A000995
CAS Number 71-58-9
Molecular Formula

C24H34O4

Purity 95%
Target Estrogen/progestogen Receptor
Solubility Soluble in DMSO > 10 mM
Storage -20°C
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
InChIKey PSGAAPLEWMOORI-PEINSRQWSA-N
SMILES CC1CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C
Reference

1: Polis CB, Achilles SL, Hel Z, Hapgood JP. Is a lower-dose, subcutaneous
contraceptive injectable containing depot medroxyprogesterone acetate likely to
impact women/’s risk of HIV? Contraception. 2017 Dec 11. pii:
S0010-7824(17)30529-2. doi: 10.1016/j.contraception.2017.12.003. [Epub ahead of
print] PubMed PMID: 29242082.
<br>

2: Yuasa-Shibasaki E, Ishii S, Matsumoto S, Tomaru T, Horiguchi K, Osaki A, Ozawa
A, Shibusawa N, Satoh T, Yamada M. Hypercalcemia after the Discontinuation of
Medroxyprogesterone Acetate. Intern Med. 2017 Dec 8. doi:
10.2169/internalmedicine.9036-17. [Epub ahead of print] PubMed PMID: 29225247.
<br>

3: Bartz D, Maurer R, Kremen J, Fortin JM, Janiak E, Goldberg AB. High-risk
sexual behaviors while on depot medroxyprogesterone acetate as compared to oral
contraception. Contracept Reprod Med. 2017 Jan 7;2:8. doi:
10.1186/s40834-016-0035-0. eCollection 2017. PubMed PMID: 29201413; PubMed
Central PMCID: PMC5683469.
<br>

4: Tasker C, Davidow A, Roche NE, Chang TL. Depot medroxyprogesterone acetate
administration alters immune markers for HIV preference and increases
susceptibility of peripheral CD4(+) T cells to HIV infection. Immunohorizons.
2017 Nov 1;1(9):223-235. doi: 10.4049/immunohorizons.1700047. PubMed PMID:
29188238; PubMed Central PMCID: PMC5703073.
<br>

5: Roksvaag I, Skjeldestad FE. Decreasing trends in number of depot
medroxyprogesterone acetate starters in Norway – a cross-sectional study. Acta
Obstet Gynecol Scand. 2017 Nov 20. doi: 10.1111/aogs.13262. [Epub ahead of print]
PubMed PMID: 29156102.
<br>

6: Tamauchi S, Kajiyama H, Utsumi F, Suzuki S, Niimi K, Sakata J, Mizuno M,
Shibata K, Kikkawa F. Efficacy of medroxyprogesterone acetate treatment and
retreatment for atypical endometrial hyperplasia and endometrial cancer. J Obstet
Gynaecol Res. 2017 Nov 9. doi: 10.1111/jog.13473. [Epub ahead of print] PubMed
PMID: 29121428.
<br>

7: Woods MW, Zahoor MA, Dizzell S, Verschoor CP, Kaushic C. Medroxyprogesterone
acetate-treated human, primary endometrial epithelial cells reveal unique gene
expression signature linked to innate immunity and HIV-1 susceptibility. Am J
Reprod Immunol. 2018 Jan;79(1). doi: 10.1111/aji.12781. Epub 2017 Nov 6. PubMed
PMID: 29105931.

<br>
8: Zhang J, Mao X, Wang Y, Chen Q, Lu X, Hong Q, Kuang Y. Neonatal outcomes and
congenital malformations in children born after human menopausal gonadotropin and
medroxyprogesterone acetate treatment cycles. Arch Gynecol Obstet. 2017
Dec;296(6):1207-1217. doi: 10.1007/s00404-017-4537-z. Epub 2017 Sep 25. PubMed
PMID: 28948397.
<br>

9: Guo H, Wang Y, Chen Q, Chai W, Sun L, Ai A, Fu Y, Lyu Q, Kuang Y. Use of
medroxyprogesterone acetate in women with ovarian endometriosis undergoing
controlled ovarian hyperstimulation for in vitro fertilization. Sci Rep. 2017 Sep
20;7(1):11927. doi: 10.1038/s41598-017-12151-7. PubMed PMID: 28931865; PubMed
Central PMCID: PMC5607235.
<br>

10: Kendall PD, Chen MJ. Case report of induced medical abortion following depot
administration of medroxyprogesterone acetate. Int J Gynaecol Obstet. 2017
Dec;139(3):371-372. doi: 10.1002/ijgo.12303. Epub 2017 Sep 7. PubMed PMID:
28833078.

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