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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

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=C(Cl)C4=CC(=O)CC[C@]34C

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

Molecular Formula C23H29ClO4
Molecular Weight 404.927
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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 Chlormadinone acetate was withdrawn from the market in the USA, but it is still being used in Europe under the name Belara.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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
BELARA

Approved Use

BELARA is a hormonal contraceptive.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1597.3 pg/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
CHLORMADINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9685 pg × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
CHLORMADINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25.3 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ETHINYL ESTRADIOL
CHLORMADINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
yes [IC50 14.2 uM]
yes [IC50 16 uM]
yes [IC50 20.2 uM]
yes [IC50 8.6 uM]
yes [Inhibition 50 uM]
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
[Ultrasonographic and lipid changes in polycystic ovary syndrome according to the type of treatment ].
2002 Jun
Vaginal dryness assessment in postmenopausal women using pH test strip.
2003 May 30
Impact of different progestins on endometrial vascularisation of postmenopausal women. A retrospective image analysis-morphometric study.
2003 Nov 20
Effects of progesterone and norethisterone on cephalexin uptake in the human intestinal cell line Caco-2.
2004 Apr
In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins.
2004 Dec 15
[Ocular changes after hormone replacement therapy in postmenopausal women. A preliminary report].
2005 Apr
A five-day gradual reduction regimen of chlormadinone reduces premenstrual anxiety and depression: a pilot study.
2006 Oct
Global update on defining and treating high-risk localized prostate cancer with leuprorelin: a Japanese perspective--the effect of primary androgen deprivation therapy on stage C prostate cancer.
2007 Jan
Effects of an oral contraceptive containing chlormadinone and ethinylestradiol on acne-prone skin of women of different age groups: an open-label, single-centre, phase IV study.
2008
Hormonal contraception: present and future.
2008 Dec
Effects of two estroprogestins containing ethynilestradiol 30 microg and drospirenone 3 mg and ethynilestradiol 30 microg and chlormadinone 2 mg on skin and hormonal hyperandrogenic manifestations.
2008 Dec
Hot flashes during androgen deprivation therapy with luteinizing hormone-releasing hormone agonist combined with steroidal or nonsteroidal antiandrogen for prostate cancer.
2009 Mar

Sample Use Guides

1 tablet (0.03 mg ethinyl estradiol and 2 mg chlormadinone acetate) daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:23:02 UTC 2023
Edited
by admin
on Fri Dec 15 17:23:02 UTC 2023
Record UNII
0SY050L61N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORMADINONE ACETATE
HSDB   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
CHLORMADINONE ACETATE [MI]
Common Name English
NORMENON
Brand Name English
Chlormadinone acetate [WHO-DD]
Common Name English
CHLORMADINONE ACETATE [EP MONOGRAPH]
Common Name English
NSC-92338
Code English
CHLORMADINONE ACETATE [HSDB]
Common Name English
CHLORMADINONE ACETATE [MART.]
Common Name English
17-(ACETYLOXY)-6-CHLOROPREGNA-4,6-DIENE-3,20-DIONE
Systematic Name English
LUTORAL
Brand Name English
6-Chloro-17-hydroxypregna-4,6-diene-3,20-dione acetate
Common Name English
PREGNA-4,6-DIENE-3,20-DIONE, 17-(ACETYLOXY)-6-CHLORO-
Systematic Name English
CHLORMADINONE ACETATE [JAN]
Common Name English
RS-1280
Code English
17.ALPHA.-ACETOXY-6-CHLORO-6,7-DEHYDROPROGESTERONE
Common Name English
6-CHLORO-6-DEHYDRO-17.ALPHA.-HYDROXYPROGESTERONE ACETATE
Common Name English
6-CHLORO-6-DEHYDRO-17.ALPHA.-ACETOXYPROGESTERONE
Common Name English
CHLORMADINONE ACETATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
Code System Code Type Description
NSC
92338
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
WIKIPEDIA
Chlormadinone acetate
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
MESH
D002715
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
MERCK INDEX
m3372
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
206-118-0
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
HSDB
3591
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
SMS_ID
100000090550
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
RXCUI
2369
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID6020274
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL110691
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
PUBCHEM
9324
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
CAS
302-22-7
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
FDA UNII
0SY050L61N
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
NCI_THESAURUS
C365
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
EVMPD
SUB01219MIG
Created by admin on Fri Dec 15 17:23:02 UTC 2023 , Edited by admin on Fri Dec 15 17:23:02 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Twenty times as potent as progesterone as far as its progestational action is concerned
Related Record Type Details
ACTIVE MOIETY