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| | Chlormadinone acetate Basic information |
| Product Name: | Chlormadinone acetate | | Synonyms: | 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 | | CAS: | 302-22-7 | | MF: | C23H29ClO4 | | MW: | 404.93 | | EINECS: | 206-118-0 | | Product Categories: | SUICALM;Steroid and Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids | | Mol File: | 302-22-7.mol |  |
| | Chlormadinone acetate Chemical 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 | neat | | 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) |
| 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. |
| | Chlormadinone acetate Usage And Synthesis |
| 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 | | Uses | Orally active progesteron with antiandrogenic activity; has been used in combinations as an oral contraceptive. Progestogen; antineoplastic (hormonal). | | 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 |
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