COCAINE

First marketed in 1860

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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	Potency
Serotonin transporter 178 Target ID: CHEMBL313 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8297	155.0 nM [Ki]
Norepinephrine transporter 191 Target ID: CHEMBL304 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8297	108.0 nM [Ki]
Dopamine transporter 180 Target ID: CHEMBL338 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12067559	Inhibitor 8297	274.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cocaine-related disorders 19 Sources: https://clinicaltrials.gov/ct2/show/NCT00000270	Primary		Phase IV 63	Cocaine Approved Use INDICATIONS 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.
Procedures and surgeries on or through accessible mucous membranes of the nasal cavities 8 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24faa247-fe12-4574-881d-445b078b3e87	Primary		Approved 8429	Cocaine Approved Use INDICATIONS 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.

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
32 mg single, intranasal Dose: 32 mg Route: intranasal Route: single Dose: 32 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
42 mg single, respiratory Dose: 42 mg Route: respiratory Route: single Dose: 42 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	healthy, 30-43 years n = 6 Health Status: healthy Age Group: 30-43 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8926741	Sources: https://pubmed.ncbi.nlm.nih.gov/8926741
8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74	Other AEs: Headache, Epistaxis... Other AEs: Headache (1.5%) Epistaxis (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%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/4443787
160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	Other AEs: Drug abuse... Other AEs: Drug abuse Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf

AEs

AE	Significance	Dose	Population
Dizziness	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Facial pain	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Nasal congestion	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Neck pain	0.4%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Anxiety	0.7%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Epistaxis	0.7%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Headache	1.5%	8 % single, intranasal Highest studied dose Dose: 8 % Route: intranasal Route: single Dose: 8 % Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000MedR.pdf Page: p. 56, 74
Adverse event	grade 5	2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/4443787	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4443787
Drug abuse		160 mg single, intranasal Recommended Dose: 160 mg Route: intranasal Route: single Dose: 160 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278 P-gp 1461 BCRP 699 OAT1 599 OAT3 642 OATP1B1 788 OATP1B3 706 OCT2 647 OCT1 512 OCT3 150	CES2 28 P-gp 1537 BCRP 561 OAT1 326 OAT3 339 OATP1B1 406 OATP1B3 350 OCT2 355

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=28 Page: 28.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	yes [IC50 1.2 uM]	unlikely (co-administration study) Comment: the relatively low plasma concentrations of cocaine resulting from therapeutic doses of GOPRELTO are not expected to raise significant drug-drug interaction concerns Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	yes [IC50 7.85 uM]	unlikely (co-administration study) Comment: the relatively low plasma concentrations of cocaine resulting from therapeutic doses of GOPRELTO are not expected to raise significant drug-drug interaction concerns Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 85 uM]
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki >1000 uM]

Drug as victim

Target	Modality	Activity	Metabolite
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT1 326	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OAT3 339	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
OCT2 355	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	no
CES2 28	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209963lbl.pdf#page=12 Page: 12.0	yes
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209963Orig1s000ClinPharmR.pdf#page=27 Page: 27.0	yes	BE 8

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/11561083/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L9JBL
Alfa Chemistry	ACM53214
Aurora Fine Chemicals LLC	A17.902.496	http://online.aurorafinechemicals.com/info?ID=A17.902.496
ChemMol	30107819	http://www.chemmol.com/chemmol/30107819.html
ChemMol	99097714	http://www.chemmol.com/chemmol/99097714.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0602073
Compound Cloud	122142
Compound Cloud	23724835
Compound Cloud	446220
Hangzhou Yuhao Chemical Technology	RT7155
LGC Standards	LGCAMP1345.05-11	https://www.lgcstandards.com/US/en/p/LGCAMP1345.05-11
LGC Standards	LGCAMP1345.05-12	https://www.lgcstandards.com/US/en/p/LGCAMP1345.05-12
LGC Standards	LGCFOR1345.05	https://www.lgcstandards.com/US/en/p/LGCFOR1345.05
NovoSeek	446220
Sigma Aldrich	1143008\|USP
Sigma Aldrich	19330\|SIAL
Sigma Aldrich	51621\|SIAL
Sigma Aldrich	C-008\|CERILLIAN
Sigma Aldrich	C1528\|SIAL
Sigma-Aldrich	C-008_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/c008?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C8912_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c8912?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S524154	http://www.smolecule.com/products/s524154
THE BioTek	bt-264235	https://www.thebiotek.com/product/inhibitors/bt-264235
Tetrahedron	TS78461
Tocris	2833
Toronto Research Chemicals	A634018
Toronto Research Chemicals	C633500
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	CC-1775E
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0777
ZINC	ZINC000003875336	http://zinc15.docking.org/substances/ZINC000003875336

PubMed

Title	Date	PubMed
Cocaine opens the blood-brain barrier to HIV-1 invasion.	1998 Dec	10065903
Sequential neuromotor examination in children with intrauterine cocaine/polydrug exposure.	1999 Apr	10355807
Midfacial complications of prolonged cocaine snorting.	1999 Apr	10224723
Behavioral and neurochemical effects of the dopamine transporter ligand 4-chlorobenztropine alone and in combination with cocaine in vivo.	1999 Apr	10086994
'Research' versus 'real-world' patients: representativeness of participants in clinical trials of treatments for cocaine dependence.	1999 Apr 1	10217557
Dopamine D2/D3 receptors modulate cocaine's reinforcing and discriminative stimulus effects in rhesus monkeys.	1999 Apr 1	10217549
Role of cocaethylene in toxic symptoms due to repeated subcutaneous cocaine administration modified by oral doses of ethanol.	1999 Aug	10478337
Sex and menstrual cycle differences in the subjective effects from smoked cocaine in humans.	1999 Aug	10472516
Cocaine pharmacokinetics in men and in women during the follicular and luteal phases of the menstrual cycle.	1999 Aug	10432477
Brief report: frequency of maternal cocaine use during pregnancy and infant neurobehavioral outcome.	1999 Dec	10608102
Nasolacrimal duct obstruction and orbital cellulitis associated with chronic intranasal cocaine abuse.	1999 Dec	10604666
[Cocaine: its possible role in coronary arteriosclerosis and myocardial infarct. Case reports and review of the literature].	1999 Jan 21	10067115
pH-dependent cocaine-induced cardiotoxicity.	1999 Jul	10452435
Total occlusion of the left main coronary artery in a young cocaine user.	1999 Jul 1	10402051
The effects of continuous cocaine dose on the induction of behavioral tolerance and dopamine autoreceptor function.	1999 Jul 9	10448878
U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking.	1999 Jun	10435406
5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB.	1999 Jun	10371652
Pharmacological characterization of nicotine's interaction with cocaine and cocaine analogs.	1999 Jun	10336510
Triggering of myocardial infarction by cocaine.	1999 Jun 1	10351966
Choreoathetoid movements in cocaine dependence.	1999 Jun 15	10376125
Cocaine-seeking behavior and Fos expression in the amygdala produced by cocaine or a cocaine self-administration environment.	1999 Jun 29	10415707
Neuronal and behavioural abnormalities in striatal function in DARPP-32-mutant mice.	1999 Mar	10103106
A nicotine antagonist, mecamylamine, reduces cue-induced cocaine craving in cocaine-dependent subjects.	1999 Mar	10063490
Acute ischaemic colitis following intravenous cocaine use.	1999 May	10425576
Aortic thrombosis associated with cocaine use: report of two cases.	1999 May	10347264
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.	1999 May	10215643
Serotonergic function in cocaine addicts: prolactin responses to sequential D,L-fenfluramine challenges.	1999 May 15	10349036
The effects of benzamide analogues on cocaine self-administration in rhesus monkeys.	1999 Nov	10591881
Pramipexole treatment for cocaine cravings.	1999 Nov	10553755
The effect of prenatal cocaine exposure on neurobehavioral outcome: a meta-analysis.	1999 Nov-Dec	10560768
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.	1999 Oct	10490887
Association of depressive symptoms during abstinence with the subjective high produced by cocaine.	1999 Sep	10484960
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.	1999 Sep 1	10485969
Postoperative anisocoria in a patient undergoing endoscopic sinus surgery.	1999 Sep-Oct	10499761
Cocaine induces apoptosis in fetal myocardial cells through a mitochondria-dependent pathway.	2000 Jan	10604926

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 15:15:05 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:05 GMT 2023`
Record UNII	I5Y540LHVR
Record Status	`Validated (UNII)`
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Name

Type

Language

COCAINE

Common Name

English

Cocaine [WHO-DD]

Common Name

English

COCAINE [VANDF]

Common Name

English

RX-0041

Code

English

RX0041

Code

English

(R)-(-)-COCAINE

Common Name

English

COCAINE [MI]

Common Name

English

COCAINUM [HPUS]

Common Name

English

8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(BENZOYLOXY)-8-METHYL-, METHYL ESTER, (1R-(EXO,EXO))-

Common Name

English

METHYL (1R,2R,3S,5S)-3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1) OCTANE-2-CARBOXYLATE

Systematic Name

English

NEUROCAINE

Common Name

English

METHYL 3B-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLATE BENZOATE (ESTER)

Common Name

English

3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID METHYL ESTER BENZOATE (ESTER)

Common Name

English

COCAINUM

Common Name

English

COCAINE [MART.]

Common Name

English

ECGONINE METHYL ESTER BENZOATE (ESTER)

Common Name

English

BENZOYLMETHYLECGONINE

Common Name

English

COCAINE [HSDB]

Common Name

English

IDS-NC-004

Code

English

COCAINE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R02AD03

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

WHO-ATC

S02DA02

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

WHO-VATC

QS02DA02

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

WHO-VATC

QN01BC01

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

YELLOW LIST

NC 004

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

NCI_THESAURUS

C47795

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

WHO-ATC

S01HA01

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

WHO-VATC

QR02AD03

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

WHO-VATC

QS01HA01

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

DEA NO.

9041

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

WHO-ATC

N01BC01

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

CFR

21 CFR 862.3250

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

Code System Code Type Description

LACTMED

Cocaine

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

MESH

D003042

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

CHEBI

60056

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

IUPHAR

2286

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

FDA UNII

I5Y540LHVR

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

CHEBI

27958

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

EVMPD

SUB13416MIG

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

NCI_THESAURUS

C80153

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

MERCK INDEX

m3710

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

Merck Index

ECHA (EC/EINECS)

200-032-7

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

DRUG CENTRAL

723

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

ChEMBL

CHEMBL370805

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

WIKIPEDIA

COCAINE

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

DAILYMED

I5Y540LHVR

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

HSDB

6469

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

DRUG BANK

DB00907

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

CAS

50-36-2

Created by admin on Fri Dec 15 15:15:05 GMT 2023 , Edited by admin on Fri Dec 15 15:15:05 GMT 2023

PRIMARY

EPA CompTox

DTXSID2038443

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

PUBCHEM

446220

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

SMS_ID

100000079767

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

RXCUI

2653

Created by admin on Fri Dec 15 15:15:06 GMT 2023 , Edited by admin on Fri Dec 15 15:15:06 GMT 2023

PRIMARY

RxNorm

Related Record Type Details


					QL5NZ3JM5F

COCAINE HYDROBROMIDE

PARENT -> SALT/SOLVATE

Amount:


					ENI788PTL9

COCAINE ESTERASE (RBP-8000)

INHIBITOR -> TARGET

Amount:


					4007E25Z4Z

OCT-3

TRANSPORTER -> INHIBITOR


					ENI788PTL9

COCAINE ESTERASE (RBP-8000)

METABOLIC ENZYME -> SUBSTRATE

Amount:


					GG6P4Q1KNT

COCAINE SULFATE

PARENT -> SALT/SOLVATE

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					XH8T8T6WZH

COCAINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					2RT6KC9AZ6

COCAINE BORATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					6354H8D6D3

COCAINE C-11

LABELED -> NON-LABELED

Amount:


					QL5NZ3JM5F

COCAINE HYDROBROMIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					WMG69LB74K

COCAINE HYDRIODIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					WM3M8W3FYR

COCAINE CITRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					482M00274D

OCT-2

TRANSPORTER -> INHIBITOR


					ONY583280Z

OCT-1

TRANSPORTER -> INHIBITOR


					9BFT5BK9YZ

COCAINE NITRATE DIHYDRATE

PARENT -> SALT/SOLVATE

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:

Related Record Type Details


					K8J4W658QK

2'-HYDROXYCOCAINE

METABOLITE ACTIVE -> PARENT

Amount:


					5353I8I6YS

BENZOYLECGONINE

PARENT -> METABOLITE

Comments:

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

Amount: