CHLORMADINONE ACETATE

US Previously Marketed

First approved in 1965

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 Search

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16356876

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 Chlormadinone acetate was withdrawn from the market in the USA, but it is still being used in Europe under the name Belara.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 Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16356876	Antagonist 2849		3.8 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16356877	Preventing		Approved 8583	BELARA Approved Use BELARA is a hormonal contraceptive.

C_max

Value	Dose	Co-administered	Analyte	Population
1597.3 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16904418/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	CHLORMADINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
9685 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16904418/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	CHLORMADINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
25.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16904418/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	CHLORMADINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 UGT1A1 246 UGT1A3 89 UGT1A6 136 UGT1A9 148 UGT2B7 197 OAT3 747 P-gp 1741

Drug as perpetrator

Target	Modality	Activity
UGT1A1 303	inhibitor 4027 Sources: https://www.ingentaconnect.com/contentone/govi/pharmaz/2011/00000066/00000003/art00012	likely
UGT1A6 171	inhibitor 4027 Sources: https://www.ingentaconnect.com/contentone/govi/pharmaz/2011/00000066/00000003/art00012	likely
UGT1A9 155	inhibitor 4027 Sources: https://www.ingentaconnect.com/contentone/govi/pharmaz/2011/00000066/00000003/art00012	likely
UGT2B7 210	inhibitor 4027 Sources: https://www.ingentaconnect.com/contentone/govi/pharmaz/2011/00000066/00000003/art00012	yes [IC50 14.2 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=001961779, https://pubmed.ncbi.nlm.nih.gov/12736515/, https://link.springer.com/article/10.2165/00044011-200222040-00002	yes [IC50 16 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15548387/	yes [IC50 20.2 uM]
UGT1A3 99	inhibitor 4027 Sources: https://www.ingentaconnect.com/contentone/govi/pharmaz/2011/00000066/00000003/art00012	yes [IC50 8.6 uM]
OAT3 749	inhibitor 4027 Sources: https://escholarship.org/content/qt3xd9s65t/qt3xd9s65t.pdf#page=15 Page: 15.0	yes [Inhibition 50 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://link.springer.com/article/10.2165/00044011-200222040-00002	yes
CYP2C19 2141	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=001961779, https://link.springer.com/article/10.2165/00044011-200222040-00002	yes
CYP2D6 2546	inhibitor 4027 Sources: https://link.springer.com/article/10.2165/00044011-200222040-00002	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-5450	http://www.3bsc.com/index/pro_info.php?id=85252
AA Blocks	AA0073TD	https://www.aablocks.com/goods/Goods/detail?id=AA0073TD
AHH Chemical co.,ltd	MT-49149	http://www.ahhchemical.com/product/MT-49149.html
AK Scientific, Inc. (AKSCI)	M167	http://www.aksci.com/item_detail.php?cat=M167
Alfa Chemistry	ACM1961779	https://www.alfa-chemistry.com/chlormadinone-cas-1961-77-9-item-61741.htm
Ambinter	Amb17610784	http://www.ambinter.com/reference/17610784
Aurora Fine Chemicals LLC	A24.077.517	http://online.aurorafinechemicals.com/info?ID=A24.077.517
BioChemPartner	BCP16136	http://www.biochempartner.com/1961-77-9-BCP16136
BioSynth	J-012685	https://www.biosynth.com/en/products/all-products/products/J-012685.html
Chemspace	CSSB00000055757	https://chem-space.com/CSSB00000055757
Lab Network	LN01262065	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01262065
LGC Standards	DRE-A11327900AL-100	https://www.lgcstandards.com/US/en/p/DRE-A11327900AL-100
LGC Standards	DRE-C11327900	https://www.lgcstandards.com/US/en/p/DRE-C11327900
MuseChem	R049313	https://www.musechem.com/product/R049313.html
Smolecule	S627573	https://www.smolecule.com/products/s627573
THE BioTek	bt-336719	https://www.thebiotek.com/product/others/bt-336719

PubMed

Title	Date	PubMed
Hot flashes during androgen deprivation therapy with luteinizing hormone-releasing hormone agonist combined with steroidal or nonsteroidal antiandrogen for prostate cancer.	2009-03	19038426
Hormonal contraception: present and future.	2008-12	19198700
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.	2008-12	19172543
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	18840013
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.	2007-01	17229161
A five-day gradual reduction regimen of chlormadinone reduces premenstrual anxiety and depression: a pilot study.	2006-10	16971235
[Ocular changes after hormone replacement therapy in postmenopausal women. A preliminary report].	2005-04	21966755
In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins.	2004-12-15	15548387
Effects of progesterone and norethisterone on cephalexin uptake in the human intestinal cell line Caco-2.	2004-04	15056866
Impact of different progestins on endometrial vascularisation of postmenopausal women. A retrospective image analysis-morphometric study.	2003-11-20	14585519
Vaginal dryness assessment in postmenopausal women using pH test strip.	2003-05-30	12753944
[Ultrasonographic and lipid changes in polycystic ovary syndrome according to the type of treatment ].	2002-06	12148471

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

Name

Type

Language

LUTORAL

Preferred Name

English

CHLORMADINONE ACETATE

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

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