Chlormadinone acetate

For research use only. Not for therapeutic Use.

  • CAT Number: I003055
  • CAS Number: 302-22-7
  • Molecular Formula: C23H29ClO4
  • Molecular Weight: 404.93
  • Purity: ≥95%
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Chlormadinone acetate is a steroidal progestin, with antiandrogen and antiestrogenic effects.
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Chlormadinone acetate (abbreviated as CMA) (INN, USAN, BAN, JAN) (sold under brand names including Clordion, Gestafortin, Lormin, Non-Ovlon, Normenon, Verton, and many others), and also known as 17α-acetoxy-6-chloro-6-dehydroprogesterone, is a steroidal progestin with additional antiandrogen and antigonadotropic (and by extension antiestrogenic) effects. CMA has been used in the treatment of vaginal bleeding, oligomenorrhea, polymenorrhea, hypermenorrhea, secondary amenorrhea, and endometriosis. It has also been used clinically as a hormonal contraceptive, and in part due to its capacity to lower estrogen levels, but also for improved effectiveness in contraception, chlormadinone has frequently been combined with ethinylestradiol for this purpose.


Catalog Number I003055
CAS Number 302-22-7
Synonyms

17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione; 17-Acetoxy-6-chloro-6-dehydroprogesterone; 6-Chloro-17-acetoxy-4,6-pregnadiene-3,20-dione; Chronosyn; Fertiletten;

Molecular Formula C23H29ClO4
Purity ≥95%
Target Estrogen/progestogen Receptor
Solubility DMSO: ≥ 4.5 mg/mL, Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Storage -20°C Freezer
InChI 1S/C23H29ClO4/c1-13(25)23(28-14(2)26)10-7-18-16-12-20(24)19-11-15(27)5-8-21(19,3)17(16)6-9-22(18,23)4/h11-12,16-18H,5-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1
InChIKey QMBJSIBWORFWQT-DFXBJWIESA-N
SMILES CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)CCC34C)Cl)C)OC(=O)C
Reference

1: Kim SM, Lee BN, Koh JT, Chang HS, Hwang IN, Oh WM, Min KS, Hwang YC. The
effect of chlormadinone acetate on odontogenic differentiation of human dental
pulp cells: in vitro study. BMC Oral Health. 2017 May 26;17(1):89. doi:
10.1186/s12903-017-0379-0. PubMed PMID: 28549486; PubMed Central PMCID:
PMC5446736.
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2: Siegenthaler PF, Zhao Y, Zhang K, Fent K. Reproductive and transcriptional
effects of the antiandrogenic progestin chlormadinone acetate in zebrafish (Danio
rerio). Environ Pollut. 2017 Apr;223:346-356. doi: 10.1016/j.envpol.2017.01.031.
Epub 2017 Jan 22. PubMed PMID: 28118999.

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3: Grandi G, Napolitano A, Xholli A, Tirelli A, Di Carlo C, Cagnacci A. Effect of
oral contraceptives containing estradiol and nomegestrol acetate or
ethinyl-estradiol and chlormadinone acetate on primary dysmenorrhea. Gynecol
Endocrinol. 2015 Oct;31(10):774-8. doi: 10.3109/09513590.2015.1063118. Epub 2015
Aug 17. PubMed PMID: 26291811.

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4: Yildizhan R, Gokce AI, Yildizhan B, Cim N. Comparison of the effects of
chlormadinone acetate versus drospirenone containing oral contraceptives on
metabolic and hormonal parameters in women with PCOS for a period of two-year
follow-up. Gynecol Endocrinol. 2015 May;31(5):396-400. doi:
10.3109/09513590.2015.1006187. Epub 2015 Mar 4. PubMed PMID: 25739031.

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5: Kim JM, Lee JE, Ryu SH, Suh PG. Chlormadinone acetate promotes osteoblast
differentiation of human mesenchymal stem cells through the ERK signaling
pathway. Eur J Pharmacol. 2014 Mar 5;726:1-8. PubMed PMID: 24440171.
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6: Gahr M, Freudenmann RW, Connemann BJ, K&#246;lle MA, Sch&#246;nfeldt-Lecuona C. Rapid
relapse in depression following initialization of oral contraception with ethinyl
estradiol and chlormadinone acetate. Gen Hosp Psychiatry. 2014
Mar-Apr;36(2):230.e1-2. doi: 10.1016/j.genhosppsych.2013.10.014. Epub 2013 Oct
30. PubMed PMID: 24287129.
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7: Koike H, Morikawa Y, Matsui H, Shibata Y, Ito K, Suzuki K. Chlormadinone
acetate is effective for hot flush during androgen deprivation therapy. Prostate
Int. 2013;1(3):113-6. doi: 10.12954/PI.12010. Epub 2013 Sep 27. PubMed PMID:
24223412; PubMed Central PMCID: PMC3814123.

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