Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C17H21NO4.C6H8O7 |
Molecular Weight | 798.8294 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)C3=CC=CC=C3)N2C.COC(=O)[C@@H]4[C@H]5CC[C@@H](C[C@@H]4OC(=O)C6=CC=CC=C6)N5C
InChI
InChIKey=ABRXXTCCHNTUTK-QJHKOLHCSA-N
InChI=1S/2C17H21NO4.C6H8O7/c2*1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11;7-3(8)1-6(13,5(11)12)2-4(9)10/h2*3-7,12-15H,8-10H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t2*12-,13+,14-,15+;/m00./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 |
Molecular Formula | C6H8O7 |
Molecular Weight | 192.1235 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Cocaine-induced hypertension: role of the peripheral sympathetic system. | 1999 Aug |
|
Cocaine-induced severe angioedema and urticaria. | 1999 Aug |
|
Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse. | 1999 Dec |
|
Severe avascular necrosis of the nasal chambers secondary to cocaine abuse. | 1999 Dec |
|
Effects of phenytoin on cocaine self-administration in humans. | 1999 Feb 1 |
|
Chronic prenatal cocaine treatment down-regulates mu-opioid receptor mRNA expression in the brain of fetal Rhesus Macaque. | 1999 Feb 12 |
|
Initial validation of the Voris Cocaine Craving Scale: a preliminary report. | 1999 Jan |
|
Antisocial personality disorder and psychopathy in cocaine-dependent women. | 1999 Jun |
|
Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs. | 1999 Jun |
|
Triggering of myocardial infarction by cocaine. | 1999 Jun 1 |
|
Cocaine-seeking behavior and Fos expression in the amygdala produced by cocaine or a cocaine self-administration environment. | 1999 Jun 29 |
|
Phasic accumbal firing may contribute to the regulation of drug taking during intravenous cocaine self-administration sessions. | 1999 Jun 29 |
|
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine. | 1999 May |
|
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice. | 1999 Nov 15 |
|
The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis. | 1999 Nov-Dec |
|
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions. | 1999 Oct |
|
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 |
|
Association of depressive symptoms during abstinence with the subjective high produced by cocaine. | 1999 Sep |
|
Postoperative anisocoria in a patient undergoing endoscopic sinus surgery. | 1999 Sep-Oct |
|
Effects of prenatal cocaine/crack and other drug exposure on electroencephalographic sleep studies at birth and one year. | 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
Sat Dec 16 11:10:48 GMT 2023
by
admin
on
Sat Dec 16 11:10:48 GMT 2023
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Record UNII |
WM3M8W3FYR
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Record Status |
Validated (UNII)
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Record Version |
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-
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167713243
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WM3M8W3FYR
Created by
admin on Sat Dec 16 11:10:48 GMT 2023 , Edited by admin on Sat Dec 16 11:10:48 GMT 2023
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ACTIVE MOIETY |
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