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Chlormadinone acetate

CAS No.
302-22-7
Chemical Name:
Chlormadinone acetate
Synonyms
CMA;Chlormadinone;GESTAFORTIN;CHLOROMADINON 17-ACETATE;17α-acetoxy-6-chloro-4,6-pregnadiene-3,20-dione;6-Chloro-3,20-dioxopregna-4,6-dien-17-yl acetate;Cero;Retex;st155;MATROL
CBNumber:
CB9673089
Molecular Formula:
C23H29ClO4
Molecular Weight:
404.93
MDL Number:
MFCD00056471
MOL File:
302-22-7.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-27 17:00:41
Product description Number Pack Size Price
Chlormadinone acetate European Pharmacopoeia (EP) Reference Standard Y0001653 130 mg $241
Chlormadinone acetate European Pharmacopoeia (EP) Reference Standard Y0001653 y0001653 $220
Chlormadinone acetate ≥98% C5145 1g $239
Chlormadinone Acetate >97.0%(HPLC) C3116 1g $83
Chlormadinone Acetate >97.0%(HPLC) C3116 5g $204
More product size

Chlormadinone acetate Properties

Melting point 212°C
alpha D +6° (c = 1 in CHCl3)
Boiling point 512.5±50.0 °C(Predicted)
Density 1.1345 (estimate)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Solid
color Off-White to Light Yellow
λmax 285nm(EtOH)(lit.)
Merck 14,2102
BRN 2633614
Henry's Law Constant 1.8×104 mol/(m3Pa) at 25℃, HSDB (2015)
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 C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@](OC(C)=O)(C(=O)C)CC3)C=C2Cl
EWG's Food Scores 1
FDA UNII 0SY050L61N
ATC code G03DB06
NIST Chemistry Reference Chlormadinone acetate(302-22-7)
EPA Substance Registry System Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-chloro- (302-22-7)
UNSPSC Code 41116107
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  Health Hazard (GHS08)
GHS08
Signal word  Danger
Hazard statements  H351-H360
Precautionary statements  P202-P405-P501-P201-P280-P308+P313-P281
PPE Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes  T
Risk Statements  60-61-40-48
Safety Statements  53-22-36/37/39-45
WGK Germany  3
RTECS  TU3750000
HS Code  29372390
Storage Class 11 - Combustible Solids
Hazardous Substances Data 302-22-7(Hazardous Substances Data)
Toxicity mouse,LD50,intraperitoneal,3gm/kg (3000mg/kg),ENDOCRINE: ADRENAL CORTEX HYPOPLASIABEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Kiso to Rinsho. Clinical Report. Vol. 11, Pg. 571, 1977.

Chlormadinone acetate price More Price(69)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0001653 Chlormadinone acetate European Pharmacopoeia (EP) Reference Standard 302-22-7 130 mg $241 2026-04-30 Buy
Sigma-Aldrich Y0001653 Chlormadinone acetate European Pharmacopoeia (EP) Reference Standard 302-22-7 y0001653 $220 2024-03-01 Buy
Sigma-Aldrich C5145 Chlormadinone acetate ≥98% 302-22-7 1g $239 2024-03-01 Buy
TCI Chemical C3116 Chlormadinone Acetate >97.0%(HPLC) 302-22-7 1g $83 2025-07-31 Buy
TCI Chemical C3116 Chlormadinone Acetate >97.0%(HPLC) 302-22-7 5g $204 2021-12-16 Buy
Product number Packaging Price Buy
Y0001653 130 mg $241 Buy
Y0001653 y0001653 $220 Buy
C5145 1g $239 Buy
C3116 1g $83 Buy
C3116 5g $204 Buy

Chlormadinone acetate Chemical Properties,Uses,Production

Description

Chlormadinone acetate is a synthetic progestin. It binds to progesterone, androgen, and glucocorticoid receptors in vitro (Kis = 2.5, 3.8, and 16 nM, respectively, for the human receptors). Chlormadinone acetate increases the number of endometrial glands and uterine weight in β-estradiol-primed rabbits when administered at a dose of 45 μg/kg per day for five days. Chlormadinone acetate reduces testosterone-induced increases in the seminal vesicle weight of castrated male rats when administered at doses of 4.6 and 21.5 mg/kg per day for eight days.

Chemical Properties

Crystalline Solid

Originator

Chlormadinone,Teikoku Hormone Mfg

Uses

Orally active progesteron with antiandrogenic activity; has been used in combinations as an oral contraceptive. Progestogen; antineoplastic (hormonal).

Uses

tranquilizer, neuroleptic, alpha adrenergic blocker

Definition

ChEBI: Chlormadinone acetate is a corticosteroid hormone.

Manufacturing Process

10 g 6-dehydro-17α-acetoxy-progesterone was dissolved in 400 ml dioxane and 40 ml water. The solution was added to 4 g N-chlorosuccinimide and 2.4 ml 70% perchloric acid. The mixture was left at ambient temperature for 24 hours, whereupon it was poured in water, a dropping precipitate was filtered off, washed with water and dried. It was filtered through aluminum oxide and recrystallized from ether to give 6-chloro-6-dehydro-17α-acetoxyprogesterone (chlormadinone acetate). MP: 204°-206°C. [α]D= +54.6° (chloroform).

brand name

Gestafortin;Luteran;Ovosiston.

Therapeutic Function

Progestin

World Health Organization (WHO)

Chlormadinone acetate, a synthetic progestogen, was introduced in 1965 as a component in oral contraceptive preparations. In 1967, as a result of new regulations required by the United States Food and Drug Administration, chlormadinone acetate was submitted to long-term toxicity studies and by the early 1970s it was shown to be associated with an increased incidence of mammary tumours in beagle bitches which led to its withdrawal by several regulatory authorities. Subsequently the validity of the beagle bitch model as a predictor of carcinogenicity of steroid contraceptives has been contested by many national regulatory authorities and chlormadinone remains available in some countries for contraceptive purposes. In some instances it is indicated for treatment of progesterone deficiency and endometriosis, and of irregular uterine bleeding due to fibroids. (Reference: (WHODI) WHO Drug Information, 84.1, 5, 1984)

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by intraperitoneal route. Human maternal and reproductive effects by ingestion, intramuscular, and possibly other routes: ovary, uterus, cervix, vagina, and fallopian tube changes; menstrual cycle changes or disorders; changes in ferthty; and other unspecified female effects. A human teratogen that causes developmental abnormalities of the endocrine system in the fetus. Experimental teratogenic and reproductive effects. An oral contraceptive. When heated to decomposition it emits toxic fumes of Cl-.

in vitro

when compared with other progesterone derivatives, chlormadinone showed a relatively strong positional effect. chlormadinone was found to have high binding affinity to the progesterone receptor, resulting in strong progestogenic activity at the endometrium level. chlormadinone could also prevent the lh surge in the same way as progesterone. in addition, chlormadinone could weakly bind to the glucocorticoid receptor, but not to either mineralocorticoid nor estrogen receptors. chlormadinone at high doses competed effectively with androgens to block their effects and also downregulated the number of androgen receptors [1].

in vivo

results from previous rat study showed that chlormadinone at low doses, similar to cyproterone acetate, was able to selectively impaire the epididymal function and maturation of spermatozoa without appreciably changing either testicular function or pituitary gonadotrophin secretion [2].

Toxics Screening Level

The Initial Threshold Screening Level (ITSL) is 0.1 μg/m3 with an annual averaging time.

References

[1] bouchard p. chlormadinone acetate (cma) in oral contraception--a new opportunity. eur j contracept reprod health care. 2005;10 suppl 1:7-11.
[2] sharma mm,lal g,jacob d. effects of low doses of chlormadinone acetate in the rat. j reprod fertil.1976 sep;48(1):177-9.

1961-77-9
108-24-7
302-22-7
Synthesis of Chlormadinone acetate from CHLORMADINON and Acetic anhydride
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View Lastest Price from Chlormadinone acetate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Chlormadinone acetate pictures 2026-07-27 Chlormadinone acetate
302-22-7
$37.00 98.97% 10g TargetMol Chemicals Inc.
Chlormadinone acetate pictures 2023-11-21 Chlormadinone acetate
302-22-7
$1.00 1000g 99% 20ton/month Wuhan Aoliqisi New Material Technology Co., Ltd.
Chlormadinone acetate pictures 2022-12-24 Chlormadinone acetate
302-22-7
1KG 99% 100000000000 Hubei Harvest Chemical CO.,Ltd
Clormadinoneacetate 17α-acetoxy-6-chloro-4,6-pregnadiene-3,20-dione chloromadinone 17-acetate 6-Chloro-17-acetoxy-4,6-pregnadiene-3,20-dione 17α-Acetoxy-6-chloro-4,6-pregnadiene-3,20-dione, 6-Chloro-6-dehydro-17α-acetoxyprogesterone, Gestafortin, Matrol, Menstridyl, 6-Chloro-17α-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate 17-alpha-acetoxy- Chlormadinone acetate,17α-Acetoxy-6-chloro-4,6-pregnadiene-3,20-dione, 6-Chloro-17α-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate, 6-Chloro-6-dehydro-17α-acetoxyprogesterone, Gestafortin, Matrol, Mens (8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-10,13-diMethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate Chlormadinone Acetate Solution, 100ppm 6-Chloro-17α-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate 6-Chloro-6-dehydro-17α-acetoxyprogesterone 17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione 17-Acetoxy-6-chloro-6-dehydroprogesterone 17-alpha-Acetoxy-6-chloro-6,7-dehydroprogesterone 17-alpha-acetoxy-6-chloro-6-dehydroprogesterone 17alpha-Acetoxy-6-chloro-6-dehydroprogesterone 17-alpha-acetoxy-6-chloropregna-4,6-diene-3,20-dione 17alpha-Acetoxy-6-chloropregna-4,6-diene-3,20-dione 20-dione,17-(acetoxy)-6-chloro-pregna-6-diene-3 6-chloro-delta(sup6)-(17-alpha)acetoxyprogesterone 6-chloro-delta(sup6)-17-acetoxyprogesterone 6-chloro-delta(sup6)-dehydro-17-acetoxyprogesterone 6-Chloro-delta4,6-pregnadiene-17alpha-ol-3,20-dione 17-acetate 6-Chloro-delta6-17-acetoxyprogesterone 6-Chloro-delta6-dehydro-17-acetoxyprogesterone 6-Chloro-delta6-(17alpha)acetoxyprogesterone 6-Chloro-delta-6-17alpha-hydroxyprogesterone acetate 6-Chloro-pregna-4,6-dien-17alpha-ol-3,20-dione acetate 6-chloro-pregna-4,6-dien-17-alpha-ol-3,20-dioneacetate 6-Dehydro-6-chloro-17-alpha-acetoxyprogesterone 6-diene-3,20-dione,6-chloro-17-hydroxy-pregna-acetate Ay 13390-6 ay13390-6 Bovisynchron Cero Chloramdinone acetate N-(4-ethylsulfonylphenyl)carbamic acid cyclopentyl ester 6-chloro-17-alpha-acetoxy-4,6-pregnadiene-3,20-dione 6-Chloro-17alpha-acetoxy-4,6-pregnadiene-3,20-dione 6-chloro-17-alpha-hydroxy-delta(sup6)-progesteroneacetate 6-Chloro-17alpha-hydroxy-delta6-progesterone acetate 6-Chloro-17alpha-hydroxypregna-4,6-diene-3,20-dione acetate 6-chloro-17-alpha-hydroxypregna-4,6-diene-3,20-dioneacetate 6-Chloro-17-hydroxypregna-4,6-diene-3,20-dione acetate 6-Chloro-3,20-dioxopregna-4,6-dien-17-yl acetate 6-Chloro-6-dehydro-17alpha-hydroxyprogesterone acetate 6-chloro-6-dehydro-17-alpha-hydroxyprogesteroneacetate 6-chloro-delta(sup4,6)-pregnadiene-17-alpha-ol-3,20-dione17-acetate CHLOROMADION 17-ACETATE VETRANAL, 100 MG 17ALPHA-ACETOXY-6-CHLORO-4,6-PREGNADIENE-3,20-DIONE MATROL MENSTRIDYL CHLOROMADINON 17-ACETATE CHLORMADINONE 17-ACETATE CHLORMADINONE ACETATE CHLORMADINONI ACETAS ACETIC ACID (8R,9S,10R,13S,14S,17R)-17-ACETYL-6-CHLORO-10,13-DIMETHYL-3-OXO-2,3,8,9,10,11,12,13,14,15,16,17-DODECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL ESTER 6-CHLORO-17ALPHA-HYDROXY-4,6-PREGNADIENE-3,20-DIONE 17-ACETATE