Chlormadinone acetate
Explore a selection of our essential drug information below, or:
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- Experimental, Withdrawn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
- Weight
- Average: 404.93
Monoisotopic: 404.1754371 - Chemical Formula
- C23H29ClO4
- Synonyms
- Chlormadinone acetate
Pharmacology
- Indication
Not Available
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Chlormadinone acetate. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Chlormadinone acetate. Acetaminophen The metabolism of Chlormadinone acetate can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Chlormadinone acetate can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Chlormadinone acetate. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BELARA Chlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG) Tablet, film coated Oral Gedeon Richter Plc 2014-07-08 Not applicable Italy BELARA Chlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG) Tablet, film coated Oral Gedeon Richter Plc 2014-07-08 Not applicable Italy BELARA Chlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG) Tablet, film coated Oral Gedeon Richter Plc 2014-07-08 Not applicable Italy BELARA Chlormadinone acetate (2 MG) + Ethinylestradiol (0.03 MG) Tablet, film coated Oral Gedeon Richter Plc 2014-07-08 Not applicable Italy BELARA film-coated tablet 0.03mg/2mg Chlormadinone acetate (2.000 mg) + Ethinylestradiol (0.030 mg) Tablet, film coated Oral PHARMLINE MARKETING PTE. LTD. 2015-10-14 Not applicable Singapore
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Antiandrogens
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Contraceptives, Oral
- Contraceptives, Oral, Hormonal
- Contraceptives, Oral, Synthetic
- Fused-Ring Compounds
- Hormonal Contraceptives for Systemic Use
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Pregnadienes
- Pregnanes
- Reproductive Control Agents
- Steroids
- Steroids, Chlorinated
- 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
- 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]
- AIFA: Belara (Chlormadinone Acetate, Ethinylestradiol) Oral Tablet [Link]
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- FDA Federal Register: List of Drug Products That Have Been Withdrawn or Removed From the Market for Reasons of Safety or Effectiveness [Link]
- External Links
- KEGG Compound
- C12729
- ChemSpider
- 8963
- 2369
- ChEBI
- 31394
- ChEMBL
- CHEMBL110691
- ZINC
- ZINC000003876041
- Wikipedia
- Chlormadinone_acetate
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Unknown Status Not Available Pharmacogenomics / Systems Biology 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Weight Changes 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet, film coated Oral 2.000 mg Tablet, film coated Oral 2 MG Tablet Oral 5.0000 mg Tablet, film coated Oral Tablet Oral 80.000 mcg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00158 mg/mL ALOGPS logP 3.58 ALOGPS logP 3.72 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 17.83 Chemaxon pKa (Strongest Basic) -5.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 60.44 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 109.09 m3·mol-1 Chemaxon Polarizability 43.67 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002r-0009100000-91593a78932d5a258857 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-3002900000-6d1d11fcb8494f9cd61d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-08or-0096100000-80fc7eac08471423ca09 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0pbc-4009100000-a79644d0d888439ace38 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-9001000000-c6f09cfc635d60eaef6a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-074j-0952000000-e576eda06d9596431197 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.13315 predictedDeepCCS 1.0 (2019) [M+H]+ 195.02856 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.32744 predictedDeepCCS 1.0 (2019)
Drug created at November 19, 2020 23:02 / Updated at December 01, 2022 11:30