Canrenoic acid

Identification

Summary

Canrenoic acid is an aldosterone antagonist used in primary hyperaldosteronism and other disorders related to aberrant aldosterone levels.

Generic Name
Canrenoic acid
DrugBank Accession Number
DB09015
Background

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.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 358.478
Monoisotopic: 358.214409446
Chemical Formula
C22H30O4
Synonyms
  • ácido canrenoico
  • Canrenoate
  • Canrenoic acid
External IDs
  • MF 465a
  • SC 14266

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.
DrugInteraction
AbacavirCanrenoic acid may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Canrenoic acid.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension 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.
AcetaminophenCanrenoic acid may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
AcetyldigitoxinCanrenoic acid may decrease the excretion rate of Acetyldigitoxin which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Canrenoic acid which could result in a higher serum level.
AclidiniumCanrenoic acid may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
AcrivastineCanrenoic acid may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirCanrenoic acid may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Potassium canrenoateM671F9NLEA2181-04-6JTZQCHFUGHIPDF-RYVBEKKQSA-M
International/Other Brands
Soludactone (Pfizer)

Categories

ATC Codes
C03DA02 — Potassium canrenoate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
17-hydroxysteroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic 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)
Affected organisms
Not Available

Chemical Identifiers

UNII
87UG89VA9K
CAS number
4138-96-9
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

References

Synthesis Reference

U.S. Patent 2,900,383.

General References
Not Available
PubChem Compound
656615
PubChem Substance
310264973
ChemSpider
570976
RxNav
618970
ChEBI
50156
ChEMBL
CHEMBL1616951
ZINC
ZINC000003938750
Drugs.com
Drugs.com Drug Page
Wikipedia
Potassium_canrenoate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / COVID-19 Pneumonia1
3CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
2Not Yet RecruitingPreventionBrain Dead Organ Donors1
2Not Yet RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / COVID-19 Acute Respiratory Distress Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionParenteral
Tablet, film coatedOral100 MG
TabletOral
Tablet, coatedOral
TabletOral100 MG
TabletOral25 MG
TabletOral50 MG
Tablet, film coatedOral200 MG
Injection, powder, for solutionIntravenous200 MG/2ML
SolutionIntravenous200 mg
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

Drug created on June 23, 2014 17:28 / Updated on September 18, 2021 12:37