Canrenoic acid

Identification

Name
Canrenoic acid
Accession Number
DB09015
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Canrenoic acid (as the salt potassium canrenoate) is an aldosterone antagonist. Like spironolactone, it is a prodrug, which is metabolized to canrenone in the body.

Structure
Thumb
Synonyms
  • ácido canrenoico
  • Canrenoate
External IDs
MF 465a / SC 14266
Product Ingredients
IngredientUNIICASInChI Key
Potassium canrenoateM671F9NLEA2181-04-6JTZQCHFUGHIPDF-RYVBEKKQSA-M
International/Other Brands
Soludactone (Pfizer)
Categories
UNII
87UG89VA9K
CAS number
4138-96-9
Weight
Average: 358.478
Monoisotopic: 358.214409446
Chemical Formula
C22H30O4
InChI Key
PBKZPPIHUVSDNM-WNHSNXHDSA-N
InChI
InChI=1S/C22H30O4/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21,26)12-8-19(24)25/h3-4,13,16-18,26H,5-12H2,1-2H3,(H,24,25)/t16-,17+,18+,20+,21+,22-/m1/s1
IUPAC Name
3-[(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]propanoic acid
SMILES
[H][C@@]12CC[C@@](O)(CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Canrenoic acid.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Canrenoic acid.
AcemetacinThe therapeutic efficacy of Canrenoic acid can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe risk or severity of hyperkalemia can be increased when Acetylsalicylic acid is combined with Canrenoic acid.
AgmatineThe risk or severity of hyperkalemia can be increased when Agmatine is combined with Canrenoic acid.
AlclofenacThe risk or severity of hyperkalemia can be increased when Canrenoic acid is combined with Alclofenac.
AlfentanilThe therapeutic efficacy of Canrenoic acid can be decreased when used in combination with Alfentanil.
AliskirenThe risk or severity of hyperkalemia can be increased when Canrenoic acid is combined with Aliskiren.
AlminoprofenThe risk or severity of hyperkalemia can be increased when Canrenoic acid is combined with Alminoprofen.
AlphacetylmethadolThe therapeutic efficacy of Canrenoic acid can be decreased when used in combination with Alphacetylmethadol.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,900,383.

General References
Not Available
External Links
PubChem Compound
656615
PubChem Substance
310264973
ChemSpider
570976
ChEBI
50156
ChEMBL
CHEMBL1616951
Drugs.com
Drugs.com Drug Page
Wikipedia
Potassium_canrenoate
ATC Codes
C03DA02 — Potassium canrenoate

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165U.S. Patent 2,900,383.
Predicted Properties
PropertyValueSource
Water Solubility0.0442 mg/mLALOGPS
logP2.73ALOGPS
logP2.93ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.98 m3·mol-1ChemAxon
Polarizability40.44 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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
Steroid acids / 3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Tertiary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / Steroid acid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclohexenone / Cyclic alcohol / Tertiary alcohol / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
monocarboxylic acid, 3-oxo Delta(4)-steroid, steroid acid (CHEBI:50156) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030154)

Drug created on June 23, 2014 11:28 / Updated on November 02, 2018 08:59