Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H21NO4 |
Molecular Weight | 303.3529 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)C3=CC=CC=C3)N2C
InChI
InChIKey=ZPUCINDJVBIVPJ-LJISPDSOSA-N
InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
DescriptionSources: https://www.drugbank.ca/drugs/DB00907Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11895133 | https://www.ncbi.nlm.nih.gov/pubmed/12067559 | https://www.ncbi.nlm.nih.gov/pubmed/17255098 | https://www.ncbi.nlm.nih.gov/pubmed/19897082
Sources: https://www.drugbank.ca/drugs/DB00907
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11895133 | https://www.ncbi.nlm.nih.gov/pubmed/12067559 | https://www.ncbi.nlm.nih.gov/pubmed/17255098 | https://www.ncbi.nlm.nih.gov/pubmed/19897082
Cocaine is an alkaloid ester extracted from the leaves of plants including coca. Cocaine 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. Cocaine is addictive due to its effect on the reward pathway in the brain. After a short period of use, there is a high risk that dependence will occur. Its use also increases the risk of stroke, myocardial infarction, lung problems in those who smoke it, blood infections, and sudden cardiac death. Cocaine sold on the street is commonly mixed with local anesthetics, cornstarch, quinine, or sugar which can result in additional toxicity. Following repeated doses, a person may have decreased the ability to feel pleasure and be very physically tired. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This results in greater concentrations of these three neurotransmitters in the brain. It can easily cross the blood-brain barrier and may lead to the breakdown of the barrier.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL313 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559 |
155.0 nM [Ki] | ||
Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559 |
108.0 nM [Ki] | ||
Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559 |
274.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Cocaine Approved UseINDICATIONS AND USAGE. Cocaine hydrochloride topical solution is indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities. |
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Primary | Cocaine Approved UseINDICATIONS AND USAGE. Cocaine hydrochloride topical solution is indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
550 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
COCAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
840 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
COCAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
78.9 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7242115/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
COCAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
25 mg single, intravenous Dose: 25 mg Route: intravenous Route: single Dose: 25 mg Sources: |
healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: |
|
32 mg single, intranasal Dose: 32 mg Route: intranasal Route: single Dose: 32 mg Sources: |
healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: |
|
42 mg single, respiratory Dose: 42 mg Route: respiratory Route: single Dose: 42 mg Sources: |
healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: |
|
8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Other AEs: Headache, Epistaxis... Other AEs: Headache (1.5%) Sources: Page: p. 56, 74Epistaxis (0.7%) Anxiety (0.7%) Foreign body sensation in eyes (0.4%) Facial pain (0.4%) Neck pain (0.4%) Dizziness (0.4%) Nasal congestion (0.4%) |
2 g single, oral Overdose |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: |
Other AEs: Adverse event... |
160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Drug abuse... Other AEs: Drug abuse Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 0.4% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Facial pain | 0.4% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Foreign body sensation in eyes | 0.4% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Nasal congestion | 0.4% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Neck pain | 0.4% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Anxiety | 0.7% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Epistaxis | 0.7% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Headache | 1.5% | 8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: Page: p. 56, 74 |
unhealthy, 45 years (range: 17- 83 years) n = 275 Health Status: unhealthy Age Group: 45 years (range: 17- 83 years) Sex: M+F Population Size: 275 Sources: Page: p. 56, 74 |
Adverse event | grade 5 | 2 g single, oral Overdose |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: |
Drug abuse | 160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Microbial keratitis following cocaine abuse in a soft contact lens wearer. | 1999 Apr |
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Amlodipine treatment of cocaine dependence. | 1999 Apr-Jun |
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Prolonged perioperative myocardial ischemia in a young male: due to topical intranasal cocaine? | 1999 Aug |
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Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice. | 1999 Aug |
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Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol. | 1999 Aug |
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Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans. | 1999 Aug |
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Cocaine-induced hypertension: role of the peripheral sympathetic system. | 1999 Aug |
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Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine). | 1999 Aug 25 |
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Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome. | 1999 Dec |
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Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse. | 1999 Dec |
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Severe avascular necrosis of the nasal chambers secondary to cocaine abuse. | 1999 Dec |
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Comparative effects of sodium bicarbonate and sodium chloride on reversing cocaine-induced changes in the electrocardiogram. | 1999 Dec |
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Cocaine-induced acute renal failure without rhabdomyolysis. | 1999 Dec |
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Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice. | 1999 Dec 15 |
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Gender differences in treatment-seeking cocaine abusers--implications for treatment and prognosis. | 1999 Fall |
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pH-dependent cocaine-induced cardiotoxicity. | 1999 Jul |
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Distinct features of seizures induced by cocaine and amphetamine analogs. | 1999 Jul 21 |
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The effects of continuous cocaine dose on the induction of behavioral tolerance and dopamine autoreceptor function. | 1999 Jul 9 |
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A case of mutism subsequent to cocaine abuse. | 1999 Jul-Sep |
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Effects of dopamine receptor antagonists (D1 and D2) on the demand for smoked cocaine base in rhesus monkeys. | 1999 Jun |
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U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking. | 1999 Jun |
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[Centrofacial necrosis secondary to cocaine use]. | 1999 Jun-Jul |
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Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma. | 1999 Nov |
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The effects of cocaine on mood and sleep in cocaine-dependent males. | 1999 Nov |
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The effects of benzamide analogues on cocaine self-administration in rhesus monkeys. | 1999 Nov |
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Pramipexole treatment for cocaine cravings. | 1999 Nov |
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Level of in utero cocaine exposure and neonatal ultrasound findings. | 1999 Nov |
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Dopamine transporter mRNA in autopsy studies of chronic cocaine users. | 1999 Nov 10 |
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Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice. | 1999 Nov 15 |
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Alcohol plus cocaine prenatally is more deleterious than either drug alone. | 1999 Nov-Dec |
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The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis. | 1999 Nov-Dec |
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Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions. | 1999 Oct |
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Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure. | 1999 Oct |
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Antagonism of 5-hydroxytryptamine(4) receptors attenuates hyperactivity induced by cocaine: putative role for 5-hydroxytryptamine(4) receptors in the nucleus accumbens shell. | 1999 Oct |
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Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys. | 1999 Oct |
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A role for the bed nucleus of the stria terminalis, but not the amygdala, in the effects of corticotropin-releasing factor on stress-induced reinstatement of cocaine seeking. | 1999 Oct 15 |
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Urticarial vasculitis following cocaine use. | 1999 Sep |
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Homozygosity at the dopamine DRD3 receptor gene in cocaine dependence. | 1999 Sep |
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Effects of chronic 'Binge' cocaine administration on plasma ACTH and corticosterone levels in mice deficient in DARPP-32. | 1999 Sep |
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Long-term changes in connexin32 gap junction protein and mRNA expression following cocaine self-administration in rats. | 1999 Sep |
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Cocaine induced myocardial infarction. | 1999 Sep |
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Association of depressive symptoms during abstinence with the subjective high produced by cocaine. | 1999 Sep |
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Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures. | 1999 Sep |
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Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence. | 1999 Sep 1 |
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Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects. | 1999 Sep 13 |
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Postoperative anisocoria in a patient undergoing endoscopic sinus surgery. | 1999 Sep-Oct |
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Dose-related neurobehavioral effects of chronic cocaine use. | 1999 Summer |
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Using eye movement desensitization and reprocessing to reduce cocaine cravings. | 2000 Jan |
|
Effects of prenatal cocaine/crack and other drug exposure on electroencephalographic sleep studies at birth and one year. | 2000 Jan |
|
Cocaine induces apoptosis in fetal myocardial cells through a mitochondria-dependent pathway. | 2000 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01746940
Cocaine HCl 10% topical solution, up to 4 mL, is applied for 20 minutes via cotton pledget(s)
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16386305
Neuronal cultures were prepared from 18-day-old Sprague–Dawley rat fetuses. Cultures were used for neurotoxicity experiments after 12 days in culture. To assess any toxic effects of cocaine per se, 10 mL aliquots of three different dilutions of the cocaine stock solution (0.1–10 mM final concentration in the medium) were added to cell cultures. Appropriate vehicle controls (same volume of solvent added) were included for each group.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
R02AD03
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WHO-ATC |
S02DA02
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WHO-VATC |
QS02DA02
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WHO-VATC |
QN01BC01
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YELLOW LIST |
NC 004
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NCI_THESAURUS |
C47795
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WHO-ATC |
S01HA01
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WHO-VATC |
QR02AD03
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WHO-VATC |
QS01HA01
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DEA NO. |
9041
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WHO-ATC |
N01BC01
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CFR |
21 CFR 862.3250
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Cocaine
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D003042
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60056
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2286
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I5Y540LHVR
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27958
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SUB13416MIG
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C80153
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m3710
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200-032-7
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723
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CHEMBL370805
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COCAINE
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I5Y540LHVR
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6469
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DB00907
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50-36-2
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DTXSID2038443
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446220
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100000079767
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2653
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PRIMARY | RxNorm |
ACTIVE MOIETY
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