Chlormadinone acetate
Chemical compound / From Wikipedia, the free encyclopedia
Dear Wikiwand AI, let's keep it short by simply answering these key questions:
Can you list the top facts and stats about Chlormadinone acetate?
Summarize this article for a 10 year old
Chlormadinone acetate (CMA), sold under the brand names Belara, Gynorelle, Lutéran, and Prostal among others, is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy, as a component of menopausal hormone therapy, in the treatment of gynecological disorders, and in the treatment of androgen-dependent conditions like enlarged prostate and prostate cancer in men and acne and hirsutism in women.[1][5][7][2][8][9][10] It is available both at a low dose in combination with an estrogen in birth control pills and, in a few countries like France and Japan, at low, moderate, and high doses alone for various indications.[11] It is taken by mouth.[1]
Clinical data | |
---|---|
Trade names | Belara, Lutéran, Prostal, others |
Other names | CMA; RS-1280; ICI-39575; STG-155; NSC-92338; 17α-Acetoxy-6-chloro-6-dehydroprogesterone; 17α-Acetoxy-6-chloropregna-4,6-diene-3,20-dione |
Routes of administration | By mouth[1] |
Drug class | Progestogen; Progestin; Progestogen ester; Antigonadotropin; Steroidal antiandrogen |
ATC code | |
Legal status | |
Legal status |
|
Pharmacokinetic data | |
Bioavailability | 100%[1][2][3] |
Protein binding | 96.6–99.4% (to albumin and not to SHBGTooltip sex hormone-binding globulin or CBGTooltip corticosteroid-binding globulin)[1][2] |
Metabolism | Liver (reduction, hydroxylation, deacetylation, conjugation)[1][3] |
Metabolites | • 3α-Hydroxy-CMA[4][1] • 3β-Hydroxy-CMA[4][1] • Others[1] |
Elimination half-life | 25–89 hours[5][1][2][6] |
Excretion | Urine: 33–45%[6][2] Feces: 24–41%[6][2] |
Identifiers | |
| |
CAS Number |
|
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.005.563 |
Chemical and physical data | |
Formula | C23H29ClO4 |
Molar mass | 404.93 g·mol−1 |
3D model (JSmol) | |
| |
|
Side effects of the combination of an estrogen and CMA include menstrual irregularities, headaches, nausea, breast tenderness, vaginal discharge, and others.[2] At high dosages, CMA can cause sexual dysfunction, demasculinization, adrenal insufficiency, and changes in carbohydrate metabolism among other adverse effects.[12][13] The drug is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It is also an antiandrogen, and hence is an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone.[1] Due to its progestogenic activity, CMA has antigonadotropic effects.[1][14][15] The medication has weak glucocorticoid activity and no other important hormonal activity.[1]
CMA was discovered in 1959 and was introduced for medical use in 1965.[16][17][18] It may be considered a "first-generation" progestin.[19] The medication was withdrawn in some countries in 1970 due to concerns about mammary toxicity observed in dogs, but this turned out not to apply to humans.[7][20][21][22][23] CMA is available widely throughout the world in birth control pills, but is notably not marketed in any predominantly English-speaking countries.[24][11] It is available alone in only a few countries, including France, Mexico, Japan, and South Korea.[24][11]