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Chlormadinone acetate

Product Name
Chlormadinone acetate
CAS No.
302-22-7
Chemical Name
Chlormadinone acetate
Synonyms
CMA;Chlormadinone;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;Lormin
CBNumber
CB9673089
Molecular Formula
C23H29ClO4
Formula Weight
404.93
MOL File
302-22-7.mol
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Chlormadinone acetate Property

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
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)
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Safety

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
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.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H351Suspected of causing cancer

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001653
Product name
Chlormadinone acetate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001653
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
C5145
Product name
Chlormadinone acetate
Purity
≥98%
Packaging
1g
Price
$239
Updated
2024/03/01
TCI Chemical
Product number
C3116
Product name
Chlormadinone Acetate
Purity
>97.0%(HPLC)
Packaging
1g
Price
$83
Updated
2024/03/01
TCI Chemical
Product number
C3116
Product name
Chlormadinone Acetate
Purity
>97.0%(HPLC)
Packaging
5g
Price
$204
Updated
2021/12/16
Cayman Chemical
Product number
29392
Product name
Chlormadinone Acetate
Packaging
500mg
Price
$61
Updated
2024/03/01
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Chlormadinone acetate Chemical Properties,Usage,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].

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.

Chlormadinone acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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Chlormadinone acetate Suppliers

Americas 1 Belgium 1 Brazil 1 Canada 4 China 213 Czech Republic 1 Europe 3 France 4 Germany 8 India 22 Israel 1 Italy 1 Japan 8 Norway 1 Switzerland 1 United Kingdom 13 United States 39 Venezuela 1 Global 323
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View Lastest Price from Chlormadinone acetate manufacturers

Wuhan Haorong Biotechnology Co.,Ltd
Product
Chlormadinone acetate 302-22-7
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000
Release date
2023-07-27
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Chlormadinone acetate 302-22-7
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-23
Nantong Guangyuan Chemicl Co,Ltd
Product
Chlormadinone Acetate 302-22-7
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2023-11-03

302-22-7, Chlormadinone acetate Related Search:

Isopropyl acetate Sodium acetate Vinyl acetate Ethyl acetate Magnesium acetate Sodium acetate trihydrate Epichlorohydrin Ammonium acetate Acetic acid Butyl acetate Benzyl acetate Cellulose acetate Chloroacetic acid Chlorophacinone ACETATE Cyproterone acetate Difluorochloromethane CIS-11-HEXADECENAL

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  • 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
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  • 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
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  • 6-Chloro-17α-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate
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  • 17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione
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  • 6-chloro-delta(sup6)-(17-alpha)acetoxyprogesterone
  • 6-chloro-delta(sup6)-17-acetoxyprogesterone
  • 6-chloro-delta(sup6)-dehydro-17-acetoxyprogesterone
  • 6-Chloro-delta<sup>4,6</sup>-pregnadiene-17alpha-ol-3,20-dione 17-acetate
  • 6-Chloro-delta<sup>6</sup>-17-acetoxyprogesterone
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  • 6-Chloro-delta-6-17alpha-hydroxyprogesterone acetate
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  • 6-chloro-pregna-4,6-dien-17-alpha-ol-3,20-dioneacetate
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  • 6-diene-3,20-dione,6-chloro-17-hydroxy-pregna-acetate
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  • 6-chloro-17-alpha-hydroxy-delta(sup6)-progesteroneacetate
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