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Approved, Withdrawn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
  • 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][[email protected]@]12CC[[email protected]@](O)(CCC(O)=O)[[email protected]@]1(C)CC[[email protected]@]1([H])[[email protected]@]2([H])C=CC2=CC(=O)CC[[email protected]]12C

Pharmacology

Indication
Not Available
Structured Indications
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
DrugInteractionDrug group
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Canrenoic acid.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Canrenoic acid.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Alphaprodine is combined with Canrenoic acid.Illicit
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Canrenoic acid.Experimental, Illicit, Withdrawn
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Canrenoic acid.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Canrenoic acid.Approved, Illicit, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Canrenoic acid.Illicit, Investigational, Vet Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Canrenoic acid.Approved, Illicit
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Canrenoic acid.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Canrenoic acid.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Canrenoic acid.Approved, Investigational
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Canrenoic acid.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Canrenoic acid.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Canrenoic acid.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Canrenoic acid.Approved, Illicit
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Canrenoic acid.Experimental
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Canrenoic acid.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Canrenoic acid.Illicit, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Canrenoic acid.Approved, Illicit, Investigational, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Canrenoic acid.Approved, Illicit, Investigational
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Canrenoic acid.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Canrenoic acid.Approved, Illicit
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Canrenoic acid.Approved, Investigational
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Canrenoic acid.Approved, Investigational
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Canrenoic acid.Approved
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Canrenoic acid.Illicit
MeptazinolThe risk or severity of adverse effects can be increased when Meptazinol is combined with Canrenoic acid.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Canrenoic acid.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Canrenoic acid.Approved, Illicit
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Canrenoic acid.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Canrenoic acid.Approved
NicomorphineThe risk or severity of adverse effects can be increased when Nicomorphine is combined with Canrenoic acid.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Canrenoic acid.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Canrenoic acid.Approved, Illicit
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Canrenoic acid.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Canrenoic acid.Approved, Investigational, Vet Approved
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Canrenoic acid.Approved, Vet Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Canrenoic acid.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Phenazocine is combined with Canrenoic acid.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Phenoperidine is combined with Canrenoic acid.Experimental
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Canrenoic acid.Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Canrenoic acid.Approved
Sodium phosphateCanrenoic acid may increase the nephrotoxic activities of Sodium phosphate.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Canrenoic acid.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Canrenoic acid.Approved
TilidineThe risk or severity of adverse effects can be increased when Tilidine is combined with Canrenoic acid.Experimental
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Canrenoic acid.Approved, Investigational
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 December 01, 2017 17:28