Benzoylecgonine

Identification

Name
Benzoylecgonine
Accession Number
DB01515
Type
Small Molecule
Groups
Experimental, Illicit
Description

Benzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. It is the main pharmaceutical ingredient in the investigational drug Esterom, a topical solution used for the relief of muscle pain that is not FDA approved or on the market in the United States. [1]

Structure
Thumb
Synonyms
  • (-)-benzoylecgonine
  • (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
  • 3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
  • Ecgonine benzoate
  • O-benzoyl-(-)-ecgonine
  • O-benzoylecgonine
External IDs
DEA No. 9180
International/Other Brands
Esterom
Categories
UNII
5353I8I6YS
CAS number
519-09-5
Weight
Average: 289.3264
Monoisotopic: 289.131408101
Chemical Formula
C16H19NO4
InChI Key
GVGYEFKIHJTNQZ-RFQIPJPRSA-N
InChI
InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
IUPAC Name
(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
SMILES
[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(O)=O)N2C

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
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Lowell M. Somers, James E. Wynn, "Derivatives of benzoylecgonine, ecgonine and ecgonidine and methods for preparing and using same." U.S. Patent US5559123, issued Sep 24, 1996.

US5559123
General References
  1. McDonald S, Lunte C: Determination of the dermal penetration of esterom components using microdialysis sampling. Pharm Res. 2003 Nov;20(11):1827-34. [PubMed:14661928]
External Links
KEGG Compound
C10847
PubChem Compound
448223
PubChem Substance
46508112
ChemSpider
395095
ChEBI
41001
ChEMBL
CHEMBL1231248
HET
BCG
Wikipedia
Benzoylecgonine
PDB Entries
1qyg

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Cambridge Isotope Laboratories Inc.
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5559123No1996-09-242016-09-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.82 mg/mLALOGPS
logP1.71ALOGPS
logP-0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.39 m3·mol-1ChemAxon
Polarizability29.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5582
Blood Brain Barrier+0.7638
Caco-2 permeable+0.7164
P-glycoprotein substrateSubstrate0.5624
P-glycoprotein inhibitor IInhibitor0.6316
P-glycoprotein inhibitor IINon-inhibitor0.9291
Renal organic cation transporterInhibitor0.6439
CYP450 2C9 substrateNon-substrate0.6808
CYP450 2D6 substrateNon-substrate0.8793
CYP450 3A4 substrateSubstrate0.6372
CYP450 1A2 substrateNon-inhibitor0.8832
CYP450 2C9 inhibitorNon-inhibitor0.9445
CYP450 2D6 inhibitorNon-inhibitor0.8493
CYP450 2C19 inhibitorNon-inhibitor0.954
CYP450 3A4 inhibitorNon-inhibitor0.955
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.973
Ames testNon AMES toxic0.7273
CarcinogenicityNon-carcinogens0.9676
BiodegradationNot ready biodegradable0.5363
Rat acute toxicity2.8083 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8437
hERG inhibition (predictor II)Non-inhibitor0.8286
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Tropane alkaloids / Piperidinecarboxylic acids / Benzoyl derivatives / N-alkylpyrrolidines / Dicarboxylic acids and derivatives / Trialkylamines / Carboxylic acid esters / Amino acids / Carboxylic acids / Azacyclic compounds
show 4 more
Substituents
Benzoate ester / Piperidinecarboxylic acid / Tropane alkaloid / Benzoyl / Dicarboxylic acid or derivatives / Piperidine / N-alkylpyrrolidine / Pyrrolidine / Amino acid or derivatives / Carboxylic acid ester
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tropane alkaloid, benzoate ester (CHEBI:41001)

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:02