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. |
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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 |
---|---|---|
Cocaine opens the blood-brain barrier to HIV-1 invasion. | 1998 Dec |
|
Symptomatic overlap of cocaine intoxication and acute schizophrenia at emergency presentation. | 1999 |
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Microbial keratitis following cocaine abuse in a soft contact lens wearer. | 1999 Apr |
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Midfacial complications of prolonged cocaine snorting. | 1999 Apr |
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RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration. | 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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Cocaine pharmacokinetics in men and in women during the follicular and luteal phases of the menstrual cycle. | 1999 Aug |
|
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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Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal 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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Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice. | 1999 Dec 15 |
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Severe renal arterio-arteriolosclerosis after cocaine use. | 1999 Feb |
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The evaluation of cocaine-induced chest pain with acute myocardial perfusion imaging. | 1999 Feb |
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[Cerebral infarction caused after cocaine consumption]. | 1999 Jan |
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pH-dependent cocaine-induced cardiotoxicity. | 1999 Jul |
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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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Effects of dopamine receptor antagonists (D1 and D2) on the demand for smoked cocaine base in rhesus monkeys. | 1999 Jun |
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5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB. | 1999 Jun |
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Antisocial personality disorder and psychopathy in cocaine-dependent women. | 1999 Jun |
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Effects of the 5-HT2C/2B antagonist SB 206553 on hyperactivity induced by cocaine. | 1999 Jun |
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Triggering of myocardial infarction by cocaine. | 1999 Jun 1 |
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Choreoathetoid movements in cocaine dependence. | 1999 Jun 15 |
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Cocaine-seeking behavior and Fos expression in the amygdala produced by cocaine or a cocaine self-administration environment. | 1999 Jun 29 |
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Stress-induced craving and stress response in cocaine dependent individuals. | 1999 Mar |
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Neuronal and behavioural abnormalities in striatal function in DARPP-32-mutant mice. | 1999 Mar |
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Neuropsychological deficits in withdrawn cocaine-dependent males. | 1999 May |
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Serotonergic function in cocaine addicts: prolactin responses to sequential D,L-fenfluramine challenges. | 1999 May 15 |
|
Chronic inhaled cocaine abuse may predispose to the development of pancreatic adenocarcinoma. | 1999 Nov |
|
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys. | 1999 Nov |
|
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice. | 1999 Nov 15 |
|
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions. | 1999 Oct |
|
Cocaine-induced erythrocytosis and increase in von Willebrand factor: evidence for drug-related blood doping and prothrombotic effects. | 1999 Sep 13 |
|
Dose-related neurobehavioral effects of chronic cocaine use. | 1999 Summer |
|
Using eye movement desensitization and reprocessing to reduce cocaine cravings. | 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
Wed Jul 05 22:46:25 UTC 2023
by
admin
on
Wed Jul 05 22:46:25 UTC 2023
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Record UNII |
I5Y540LHVR
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Record Status |
Validated (UNII)
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Record Version |
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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
Created by
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Code System | Code | Type | Description | ||
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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 |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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INHIBITOR -> TARGET |
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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PARENT -> SALT/SOLVATE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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LABELED -> NON-LABELED |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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PARENT -> SALT/SOLVATE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
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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
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Seen when cocaine use is combined with alcohol
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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