NAV

Chlormadinone acetate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Chlormadinone acetate is a progestin indicated in combination with an estrogen for birth control.

Generic Name
Chlormadinone acetate
DrugBank Accession Number
DB15903
Background

Chlormadinone acetate is a progesterone derivative first synthesized in 1961. In the US, chlormadinone acetate was formerly marketed as a component of the combination drug products Estalor-21 and C-Quens. However, the use of these drugs was associated with the development of mammary tumors in dogs. In 1972, the FDA withdrew its approval for the use of chlormadinone acetate in all products.3,4 Chlormadinone acetate continues to be used in other countries due to its high contraceptive efficacy and tolerability.1,2

Type
Small Molecule
Groups
Experimental, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 404.93
Monoisotopic: 404.1754371
Chemical Formula
C23H29ClO4
Synonyms
  • Chlormadinone acetate
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
Capromab pendetideChlormadinone acetate may decrease effectiveness of Capromab pendetide as a diagnostic agent.
Choline C 11Chlormadinone acetate may decrease effectiveness of Choline C 11 as a diagnostic agent.
Flotufolastat F-18Chlormadinone acetate may decrease effectiveness of Flotufolastat F-18 as a diagnostic agent.
Gallium Ga-68 gozetotideChlormadinone acetate may increase effectiveness of Gallium Ga-68 gozetotide as a diagnostic agent.
Piflufolastat F 18Chlormadinone acetate may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent.
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BELARAChlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG)Tablet, film coatedOralGedeon Richter Plc2014-07-08Not applicableItaly flag
BELARAChlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG)Tablet, film coatedOralGedeon Richter Plc2014-07-08Not applicableItaly flag
BELARAChlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG)Tablet, film coatedOralGedeon Richter Plc2014-07-08Not applicableItaly flag
BELARAChlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG)Tablet, film coatedOralGedeon Richter Plc2014-07-08Not applicableItaly flag
BELARA film-coated tablet 0.03mg/2mgChlormadinone acetate (2.000 mg) + Ethinylestradiol (0.030 mg)Tablet, film coatedOralPHARMLINE MARKETING PTE. LTD.2015-10-14Not applicableSingapore flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
0SY050L61N
CAS number
302-22-7
InChI Key
QMBJSIBWORFWQT-DFXBJWIESA-N
InChI
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
IUPAC Name
(1R,3aS,3bR,9aR,9bS,11aS)-1-acetyl-5-chloro-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate
SMILES
[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=C(Cl)C2=CC(=O)CC[C@]12C

References

General References
  1. Barriga P P, Ambrosi Penazzo N, Franco Finotti M, Celis AA, Cerdas O, Chavez JA, Cuitino LA, Fernandes CE, Plata MA, Tiran-Saucedo J, Vanhauwaert PS: At 10 years of chlormadinone use in Latin America: a review. Gynecol Endocrinol. 2016 Jul;32(7):517-20. doi: 10.3109/09513590.2016.1153059. Epub 2016 Apr 26. [Article]
  2. AIFA: Belara (Chlormadinone Acetate, Ethinylestradiol) Oral Tablet [Link]
  3. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
  4. FDA Federal Register: List of Drug Products That Have Been Withdrawn or Removed From the Market for Reasons of Safety or Effectiveness [Link]
KEGG Compound
C12729
ChemSpider
8963
RxNav
2369
ChEBI
31394
ChEMBL
CHEMBL110691
ZINC
ZINC000003876041
Wikipedia
Chlormadinone_acetate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Unknown StatusNot AvailablePharmacogenomics / Systems Biology1
4Unknown StatusTreatmentWeight Changes1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Tablet, film coatedOral2.000 mg
Tablet, film coatedOral2 MG
TabletOral5.0000 mg
Tablet, film coatedOral
TabletOral80.000 mcg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00158 mg/mLALOGPS
logP3.58ALOGPS
logP3.72Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)17.83Chemaxon
pKa (Strongest Basic)-5.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area60.44 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity109.09 m3·mol-1Chemaxon
Polarizability43.67 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002r-0009100000-91593a78932d5a258857
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-3002900000-6d1d11fcb8494f9cd61d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08or-0096100000-80fc7eac08471423ca09
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbc-4009100000-a79644d0d888439ace38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9001000000-c6f09cfc635d60eaef6a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-074j-0952000000-e576eda06d9596431197
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.13315
predicted
DeepCCS 1.0 (2019)
[M+H]+195.02856
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.32744
predicted
DeepCCS 1.0 (2019)

Drug created at November 19, 2020 23:02 / Updated at December 01, 2022 11:30