Canrenone

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

Identification

Summary

Canrenone is an antimineralocorticoid and active metabolite of spironolactone used in the treatment of primary hyperaldosteronism and edematous states caused by secondary hyperaldosteronism (e.g. heart failure).

Generic Name
Canrenone
DrugBank Accession Number
DB12221
Background

Canrenone has been used in trials studying the diagnostic of Heart Failure.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 340.4559
Monoisotopic: 340.203844762
Chemical Formula
C22H28O3
Synonyms
  • Canrenone
External IDs
  • SC-9376

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
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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
AbacavirCanrenone 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 Canrenone.
AceclofenacAceclofenac may increase the excretion rate of Canrenone which could result in a lower serum level and potentially a reduction in efficacy.
AcemetacinThe therapeutic efficacy of Canrenone can be decreased when used in combination with Acemetacin.
AcetaminophenCanrenone may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
AcetyldigitoxinCanrenone may decrease the excretion rate of Acetyldigitoxin which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Canrenone which could result in a higher serum level.
AclidiniumCanrenone may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
AcrivastineCanrenone may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirCanrenone 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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Categories

ATC Codes
C03DA03 — Canrenone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Steroid lactones
Alternative Parents
3-oxosteroids / Cyclohexenones / Gamma butyrolactones / Tetrahydrofurans / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxosteroid / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Gamma butyrolactone / Hydrocarbon derivative / Ketone
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
78O20X9J0U
CAS number
976-71-6
InChI Key
UJVLDDZCTMKXJK-WNHSNXHDSA-N
InChI
InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1
IUPAC Name
(1R,3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-2,3,3a,3b,7,8,9,9a,9b,10,11,11a-dodecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione
SMILES
[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

References

General References
  1. AIFA Product Information: Luvion (canrenone) for oral/intravenous administration [Link]
Human Metabolome Database
HMDB0003033
PubChem Compound
13789
PubChem Substance
347828500
ChemSpider
13192
RxNav
1982
ChEBI
135445
ChEMBL
CHEMBL1463345
ZINC
ZINC000003881648
Wikipedia
Canrenone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHypertension, Essential Hypertension1
4Not Yet RecruitingTreatmentParoxysmal Atrial Fibrillation (PAF)1
3CompletedDiagnosticHeart Failure1
Not AvailableCompletedNot AvailableCardiac Heart Failure Patients1
Not AvailableCompletedNot AvailablePrimary Aldosteronism Due to Aldosterone Producing Adenoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
TabletOral50 MG
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0042 mg/mLALOGPS
logP2.79ALOGPS
logP3.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity97.48 m3·mol-1ChemAxon
Polarizability38.67 Å3ChemAxon
Number of Rings5ChemAxon
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-2910000000-895da7d842991e1f2631
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-3900000000-44a9709cabb5e8f1da5d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0079-0962000000-d3aa34556f83b16405c8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05tr-0962000000-924d636ff93f46fb7ccc
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Drug created on October 20, 2016 21:39 / Updated on May 21, 2021 10:22