1961-77-9

Basic information

• Product Name: CHLORMADINON
• Synonyms: 20-dione,6-chloro-17-hydroxy-pregna-6-diene-3;6-chloro-17-hydroxypregna-4,6-diene-3,20-dione;CHLORMADINON;6-chloro-17-alpha-hydroxypregna-4,6-diene-3,20-dione;PREGNA-4,6-DIENE-3,20-DIONE,6-CHLORO-17-HYDROXY-;6-Chloro-6-dehydro-17- hydroxyprogesterone;6-Chloro-6-dehydro-17-α-hydroxyprogesterone;Chlormadinone Solution, 100ppm
• CAS NO: 1961-77-9
• Molecular Formula: C₂₁H₂₇ClO₃
• Molecular Weight: 362.89
• EINECS: 217-802-3
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 1961-77-9.mol

Chemical Properties

• Melting Point: 213°C
• Boiling Point: 478.95°C (rough estimate)
• Flash Point: 260.2 °C
• Appearance: /
• Density: 1.0559 (rough estimate)
• Vapor Pressure: 2.18E-12mmHg at 25°C
• Refractive Index: 1.4585 (estimate)
• PKA: 12.87±0.70(Predicted)
• CAS DataBase Reference: CHLORMADINON(CAS DataBase Reference)
• NIST Chemistry Reference: CHLORMADINON(1961-77-9)
• EPA Substance Registry System: CHLORMADINON(1961-77-9)

Safety Data

• Hazardous Substances Data: 1961-77-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CHLORMADINON is used as an ingredient in oral contraceptives for its ability to inhibit ovulation, alter the cervical mucus, and affect the endometrium, thereby preventing pregnancy. It is typically combined with other hormones, such as estrogens, to enhance its effectiveness and reduce potential side effects.

InChI:InChI=1/C21H27ClO3/c1-12(23)21(25)9-6-16-14-11-18(22)17-10-13(24)4-7-19(17,2)15(14)5-8-20(16,21)3/h10-11,14-16,25H,4-9H2,1-3H3/t14-,15+,16+,19-,20+,21+/m1/s1

Upstream product

• 302-22-7 chlormadinone acetate 
• 68-96-2 17-hydroxyprogesterone 
• 2477-60-3 17α-hydroxypregna-4,6-diene-3,20-dione 

Downstream Products

• 302-22-7 chlormadinone acetate 

Relevant articles and documents

Preparation method of chlormadinone acetate

A preparation method of chlormadinone acetate includes: using 17a hydroxyl progestin as a raw material, dissolving the same in an organic solvent, reacting with bromine under acid catalysis to obtaina bromination product, and enabling the bromination product to react with lithium bromide and lithium carbonate in the organic solvent for debromination to obtain 6 dehydrogenation product in the organic solvent; dissolving the 6 dehydrogenation product in the organic solvent to react with organic peroxy acid to obtain epoxide; dissolving the epoxide in the organic solvent to be in additive reaction with hydrogen chloride gas, and dehydrating in a strong acid solution to obtain chlormadinone; dissolving chlormadinone in the organic solvent to react with acetic anhydride under acid catalysis toobtain chlormadinone acetate. HPLC content is 99.0-99.5%, and total yield of four-step synthetic reaction is 80-82%. Compared with conventional synthetic methods, the preparation method is simple andconvenient to operate, economical, environment-friendly and high in synthetic total yield and in product quality, and cost is lowered by 40-45%; the solvent used in the method can be recycled, so that industrial production is facilitated greatly.

Novel C-6 substituted and unsubstituted pregnane derivatives as 5α-reductase inhibitors and their effect on hamster flank organs diameter size

The present study is addressed to ascertain the inhibitory effect of several progesterone derivatives having a chlorine substituent at C-6 (12a-12d), 15 with a bromine substituent at C-6 and 14a-14d, without any halogen atom at C-6 all having an ester side chain at C-17 (benzoate ester bearing a Cl, F and a Br atom at C-4 position of the phenyl ring) on the 5α-reductase enzyme activity present in human prostate. In addition, it was also of interest to investigate the pharmacological effect on hamster flank organs diameter size. In order to study the structure-activity relationships of steroids 12a-12d, 14a-14d and 15 we determined the concentration of these steroids that inhibited 50% of the activity of human prostate 5α-reductase enzyme (IC50), as well as the in vivo effect of these compounds in the hamster flank organs diameter size. We also ascertained, the capacity of these steroids to bind to the androgen receptors present in the rat prostate cytosol using labeled mibolerone (MIB) for monitoring the binding to the androgen receptor. The results from this study indicated that compounds 12a-12d (having a chlorine substituent at C-6), 14a-14d (lacking a halogen atom at C-6), 13 and 15 (having a bromine atom at C-6) showed an increased antiandrogenic effect (lower value for the diameter of the flank organs) as compared to the flank organs from testosterone-treated hamsters. On the other hand, the series of compounds containing a chlorine substituent at C-6 compounds (12a-12d) showed a higher antiandrogenic activity as compared to the compounds lacking a halogen atom at C-6 (14a, 14b and 14d). Although compounds 13 and 15 decreased the flank organs diameter size, however, this increase was not statistically significant as compared to that of the commercially available product finasteride. The steroidal derivatives 13, 14a-14d (lacking the chlorine substituent at C-6) and 15 (having a bromine atom at C-6) exhibited a higher 5α-reductase inhibitory activity (lower IC50 values) as compared to the series of compounds 12a-12d having the halogen substituent at C-6. Finasteride reduced the diameter size of the flank organs. The effect of this steroid and compounds 12a-12d, 13, 14a-14d and 15 on hamster flank organs can be explained by the fact that these steroids did not bind to the androgens receptor, which indicates that its mechanism of action is an inhibiting for the 5α-reductase activity. This enzyme is present in the hamster flank organs and was inhibited by the novel steroids in the human prostate homogenates.

Development of a new sensitive and specific time-resolved fluoroimmunoassay (TR-FIA) of chlormadinone acetate in the serum of treated menopausal women.

We describe the development of a serum chlormadinone acetate (CMA) time-resolved fluoroimmunoassay (TR-FIA). We prepared haptens (3-CMO-chlormadinone acetate and 6-chloropregna-4,6-dien-17,20-diol-3-one-20-hemisuccinate), biotinylated tracers (3(biotinylaminopropylamido) 3-CMO-chlormadinone acetate and 3-(6-chloropregna-4,6-dien-17,20-diol-3-one-20-hemisuccinylamino)1-biotinylaminopropane), and immunogens necessary for eliciting two antibodies (anti-chlormadinone acetate 3-CMO/BSA and anti-chlormadinone 20-hemisuccinate/BSA). The specificity of the assay was rigorously studied to eliminate possible interference by polar metabolites of CMA, particularly 17 alpha-acetoxy-6-chloro-3beta-hydroxypregna-4,6-diene-20-one (3beta-hydroxy metabolite), employing an easy-to-use ethylene glycol chromatographic step prior to immunoassay, so as to separate the polar metabolites, in particular the 3beta-hydroxy-CMA metabolite, from the intact CMA. The choice of the anti-CMA antibody was guided by the high assay sensitivity obtained with the anti-CMA 3-CMO/BSA antibody. The detection limit was 51pg/ml. Interassay reproducibility CVs were between 2.6 and 4.5%. This TR-FIA thus appeared to be a sensitive, specific, precise, and consequently well-suited method for measurement of serum CMA during a pharmacokinetic study in women.

Combined antiestrogens and antigonadotropically effective antiandrogens for the prophylaxis and therapy of hyperplasia of the prostate

A pharmaceutical composition comprising an anti-estrogen and an antigonadotropically effective anti-androgen, e.g., in a weight ratio of anti-estrogen to anti-androgen of essentially 2:1 to 1:10 is effective for the prophylaxis and therapy of prostate hyperplasia. Suitable anti-estrogens include, for example, tamoxifen. Antigonadotropically active anti-androgens preferably are steroids having anti-androgenic and progestational properties, e.g., cyproterone acetate.

Novel 17-esters of 17α-hydroxy gestogens, compositions containing such compounds, processes for their preparation and methods of treatment therewith

This invention relates to novel 17α-esters of gestogens having an antitumour activity and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds, and method of treatment therewith.