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
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
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 |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/16356876
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 Chlormadinone acetate was withdrawn from the market in the USA, but it is still being used in Europe under the name Belara.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 |
---|---|---|---|
Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16356876 |
3.8 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | BELARA Approved UseBELARA is a hormonal contraceptive. |
Cmax
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 |
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 |
CHLORMADINONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
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 |
CHLORMADINONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
likely | ||||
yes [IC50 14.2 uM] | ||||
yes [IC50 16 uM] | ||||
yes [IC50 20.2 uM] | ||||
yes [IC50 8.6 uM] | ||||
Page: 15.0 |
yes [Inhibition 50 uM] | |||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15025547
1 tablet (0.03 mg ethinyl estradiol and 2 mg chlormadinone acetate) daily.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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Edited
Fri Dec 15 17:23:02 UTC 2023
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Fri Dec 15 17:23:02 UTC 2023
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Record UNII |
0SY050L61N
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C776
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92338
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Chlormadinone acetate
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D002715
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m3372
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206-118-0
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3591
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2369
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DTXSID6020274
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CHEMBL110691
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C365
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
Twenty times as potent as progesterone as far as its progestational action is concerned
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Related Record | Type | Details | ||
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ACTIVE MOIETY |