Drug/Small Molecule:
cocaine

2D structure

Overview

Generic Names: Badrock; Bazooka; Benzoylethylecgonine; Benzoylmethylecgonine; Bernice; Bernies; Beta-Cocain; Blast; Blizzard; Blow; Bouncing Powder; Bump; Burese; C" Carrie; COC; Cabello; Candy; Carrie; Caviar; Cecil; Charlie; Chicken Scratch; Cholly; Coca; Cocain; Cocaina; Cocaine Free Base; Cocaine-M; Cocktail; Coke; Cola; Corine; D-pseudococaine; Dama Blanca; Delcaine; Depsococaine; Dextrocaine; Dust; Eritroxilina; Erytroxylin; Flake; Flex; Florida Snow; Foo Foo; Freeze; G-Rock; Girl; Gold Dust; Goofball; Green Gold; Happy Dust; Happy Powder; Happy Trails; Heaven; Hell; Isocaine; Isococain; Isococaine; Jam; Kibbles N' Bits; Kokain; Kokan; Kokayeen; L-Cocain; L-Cocaine; Lady; Leaf; Methyl Benzoylecgonine; Moonrocks; Neurocaine; Pimp's Drug; Prime Time; Rock; Sleighride; Snort; Star Dust; Star-Spangled Powder; Sugar; Sweet Stuff; Toke; Toot; Trails; Yeyo; Zip
Trade Names: Cocaine
PharmGKB Accession Id: PA449072

Description

An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake. PubChem (source: Drug Bank)

Indication

For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities. (source: Drug Bank)

ATC Therapeutic Categories

  • N01BC:Esters of benzoic acid
  • R02AD:Anesthetics, local
  • S01HA:Local anesthetics
  • S02DA:Analgesics and anesthetics

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Cocaine produces anesthesia by inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. This is achieved by reversibly binding to and inactivating sodium channels. Sodium influx through these channels is necessary for the depolarization of nerve cell membranes and subsequent propagation of impulses along the course of the nerve. Cocaine is the only local anesthetic with vasoconstrictive properties. This is a result of its blockade of norepinephrine reuptake in the autonomic nervous system. Cocaine binds differentially to the dopamine, serotonin, and norepinephrine transport proteins and directly prevents the re-uptake of dopamine, serotonin, and norepinephrine into pre-synaptic neurons. Cocaine also produces a number of indirect actions, which alter other neuromodulatory systems (i.e., opioidergic, glutamatergic, and GABAergic systems). (source: Drug Bank)

Pharmacology

Cocaine is a local anesthetic indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. Cocaine is metabolized to benzoylecgonine and ecgonine methyl ester, which are both excreted in the urine. In the presence of alcohol, a further active metabolite, cocaethylene is formed, and is more toxic then cocaine itself. (source: Drug Bank)

Absorption

Cocaine is absorbed from all sites of application, including mucous membranes and gastrointestinal mucosa. By oral or intra-nasal route, 60 to 80% of cocaine is absorbed. (source: Drug Bank)

Toxicity

Intense agitation, convulsions, hypertension, rhythm disturbance, coronary insufficiency, hyperthermia, rhabdomyolysis, and renal impairment. Oral mouse LD<sub>50</sub> = 96 mg/kg (source: Drug Bank)

Isomeric SMILES Code:

CN1C2CCC1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)OC (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
BCHE
  •   
  •   
  • PK
  • FA
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
CNR1
  • CO
  •   
  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
COMT
  •   
  •   
  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2D6
  •   
  •   
  • PK
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
DRD1
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
HOMER1
  •   
  • PD
  •   
  •   
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
DRD1 Uncurated Annotation (source: Drug Bank)
DRD3 Uncurated Annotation (source: Drug Bank)
OPRK1 Uncurated Annotation (source: Drug Bank)
SCN5A Uncurated Annotation (source: Drug Bank)
SCN10A Uncurated Annotation (source: Drug Bank)
SCN11A Uncurated Annotation (source: Drug Bank)
SLC6A1 Uncurated Annotation (source: Drug Bank)
SLC6A3 Uncurated Annotation (source: Drug Bank)
SLC6A2 Uncurated Annotation (source: Drug Bank)
SLC6A4 Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Apnea
  •   
  •   
  • PK
  • FA
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Cocaine-Related Disorders
  • CO
  •   
  •   
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00907
ChEBI ID:
27958
KEGG Compound ID:
C01416
KEGG Drug ID:
D00110
PubChem Compound ID:
5760
PubChem Substance ID:
148543
IUPHAR Ligand ID:
2286

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
Add New Alternate Name
Add New ATC Term
Add Cross Reference
Add a metabolite
Add a text annotation
Add a drug target
hint: enter a gene
    Add a drug interaction
    hint: enter a drug
    PharmGKB® is a registered trademark of HHS and is financially supported by NIH/NIGMS. It is managed at Stanford University (GM61374).
    ©2001-2010 PharmGKB.