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
Molecular Formula | C17H21NO4 |
Molecular Weight | 303.3529 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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. |
|||
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 |
---|---|---|
Antiglomerular basement membrane antibody-mediated glomerulonephritis after intranasal cocaine use. | 1999 |
|
Sequential neuromotor examination in children with intrauterine cocaine/polydrug exposure. | 1999 Apr |
|
RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration. | 1999 Apr |
|
Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol. | 1999 Aug |
|
Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans. | 1999 Aug |
|
Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome. | 1999 Dec |
|
Comparative effects of sodium bicarbonate and sodium chloride on reversing cocaine-induced changes in the electrocardiogram. | 1999 Dec |
|
Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice. | 1999 Dec 15 |
|
Gender differences in treatment-seeking cocaine abusers--implications for treatment and prognosis. | 1999 Fall |
|
Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. | 1999 Jul 22 |
|
Antisocial personality disorder and psychopathy in cocaine-dependent women. | 1999 Jun |
|
Effects of contingent and non-contingent cocaine on drug-seeking behavior measured using a second-order schedule of cocaine reinforcement in rats. | 1999 Jun |
|
[Centrofacial necrosis secondary to cocaine use]. | 1999 Jun-Jul |
|
Acute ischaemic colitis following intravenous cocaine use. | 1999 May |
|
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine. | 1999 May |
|
Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma. | 1999 Nov |
|
The effects of cocaine on mood and sleep in cocaine-dependent males. | 1999 Nov |
|
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions. | 1999 Oct |
|
Prenatal cocaine and neuromotor outcome at four months: effect of duration of exposure. | 1999 Oct |
|
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects. | 1999 Sep 13 |
|
Cocaine-induced mood disorder: prevalence rates and psychiatric symptoms in an outpatient cocaine-dependent sample. | 1999 Spring |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:36:46 UTC 2022
by
admin
on
Fri Dec 16 16:36:46 UTC 2022
|
Record UNII |
I5Y540LHVR
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
R02AD03
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-ATC |
S02DA02
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-VATC |
QS02DA02
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-VATC |
QN01BC01
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
YELLOW LIST |
NC 004
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
NCI_THESAURUS |
C47795
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-ATC |
S01HA01
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-VATC |
QR02AD03
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-VATC |
QS01HA01
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
DEA NO. |
9041
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
WHO-ATC |
N01BC01
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
||
|
CFR |
21 CFR 862.3250
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
Cocaine
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
D003042
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
60056
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
2286
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
I5Y540LHVR
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
27958
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
SUB13416MIG
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
C80153
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
M3710
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | Merck Index | ||
|
200-032-7
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
723
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
CHEMBL370805
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
COCAINE
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
I5Y540LHVR
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
6469
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
DB00907
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
50-36-2
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
DTXSID2038443
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
446220
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | |||
|
2653
Created by
admin on Fri Dec 16 16:36:46 UTC 2022 , Edited by admin on Fri Dec 16 16:36:46 UTC 2022
|
PRIMARY | RxNorm |
Related Record | Type | Details | ||
---|---|---|---|---|
|
INHIBITOR -> TARGET | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
PARENT -> SALT/SOLVATE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
PARENT -> SALT/SOLVATE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
ANALOGUE->TARGET | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT | |||
|
PARENT -> METABOLITE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Cocaine is a methyl ester of benzoylecgonine
(an alkaloid found in coca leaves or prepared by synthesis from ecgonine). as per INCB
|
||
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|