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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29ClO4
Molecular Weight 404.927
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORMADINONE ACETATE

SMILES

CC(=O)O[C@@]1(CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)=O

InChI

InChIKey=QMBJSIBWORFWQT-DFXBJWIESA-N
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

HIDE SMILES / InChI

Description

Chlormadinone acetate (CMA) is a derivative of naturally secreted progesterone that shows high affinity and activity at the progesterone receptor. It has an anti-estrogenic effect and, in contrast to natural progesterone, shows moderate anti-androgenic properties. CMA acts by blocking androgen receptors in target organs and by reducing the activity of skin 5alpha-reductase. It suppresses gonadotropin secretion and thereby reduces ovarian and adrenal androgen production. CMA shows high contraceptive efficacy by inhibiting ovulation due to its ability to suppress or disrupt endogenous gonadotropin secretion and, by this, inhibits follicular growth and maturation. In addition, it suppresses endometrial thickness and increases the viscosity of cervical mucus. Chlormadinone acetate was withdrawn from the market in the USA, but it is still being used in Europe under the name Belara.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.8 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
BELARA

Cmax

ValueDoseCo-administeredAnalytePopulation
1597.3 pg/mL
2 mg single, oral
CHLORMADINONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
9685 pg × h/mL
2 mg single, oral
CHLORMADINONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
25.3 h
2 mg single, oral
CHLORMADINONE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
1 tablet (0.03 mg ethinyl estradiol and 2 mg chlormadinone acetate) daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown