Benzoylecgonine
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Benzoylecgonine
- DrugBank Accession Number
- DB01515
- Background
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
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
- Weight
- Average: 289.3264
Monoisotopic: 289.131408101 - Chemical Formula
- C16H19NO4
- 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
Pharmacology
- Indication
Not Available
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzoate ester / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tropane alkaloid, benzoate ester (CHEBI:41001)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5353I8I6YS
- CAS number
- 519-09-5
- 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
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
- McDonald S, Lunte C: Determination of the dermal penetration of esterom components using microdialysis sampling. Pharm Res. 2003 Nov;20(11):1827-34. [Article]
- External Links
- KEGG Compound
- C10847
- PubChem Compound
- 448223
- PubChem Substance
- 46508112
- ChemSpider
- 395095
- ChEBI
- 41001
- ChEMBL
- CHEMBL1231248
- ZINC
- ZINC000002572652
- PDBe Ligand
- BCG
- Wikipedia
- Benzoylecgonine
- PDB Entries
- 1qyg / 6nfn
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Cambridge Isotope Laboratories Inc.
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5559123 No 1996-09-24 2016-09-24 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 195 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 3.82 mg/mL ALOGPS logP 1.71 ALOGPS logP -0.59 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 3.15 Chemaxon pKa (Strongest Basic) 9.54 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.84 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 76.39 m3·mol-1 Chemaxon Polarizability 29.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5582 Blood Brain Barrier + 0.7638 Caco-2 permeable + 0.7164 P-glycoprotein substrate Substrate 0.5624 P-glycoprotein inhibitor I Inhibitor 0.6316 P-glycoprotein inhibitor II Non-inhibitor 0.9291 Renal organic cation transporter Inhibitor 0.6439 CYP450 2C9 substrate Non-substrate 0.6808 CYP450 2D6 substrate Non-substrate 0.8793 CYP450 3A4 substrate Substrate 0.6372 CYP450 1A2 substrate Non-inhibitor 0.8832 CYP450 2C9 inhibitor Non-inhibitor 0.9445 CYP450 2D6 inhibitor Non-inhibitor 0.8493 CYP450 2C19 inhibitor Non-inhibitor 0.954 CYP450 3A4 inhibitor Non-inhibitor 0.955 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.973 Ames test Non AMES toxic 0.7273 Carcinogenicity Non-carcinogens 0.9676 Biodegradation Not ready biodegradable 0.5363 Rat acute toxicity 2.8083 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8437 hERG inhibition (predictor II) Non-inhibitor 0.8286
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0190000000-fa4c8676731a0cdf2985 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1930000000-4e712677b57408f9ae24 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-006x-0590000000-774c9b9fb599f0046e56 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00ac-2910000000-50cffecdf7ab2cb399df Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-3900000000-2f9f1986ee422ec54d5b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9100000000-bcc4f454f21ef5f97f0c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.9568714 predictedDarkChem Lite v0.1.0 [M-H]- 167.9033714 predictedDarkChem Lite v0.1.0 [M-H]- 162.85564 predictedDeepCCS 1.0 (2019) [M+H]+ 172.7458714 predictedDarkChem Lite v0.1.0 [M+H]+ 167.1103714 predictedDarkChem Lite v0.1.0 [M+H]+ 165.25117 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.8188714 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.77321 predictedDeepCCS 1.0 (2019)
Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51