COC

COCAINE

Created:	2000-02-25
Last modified:	2011-06-04

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8 entries where COC is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	4
Bond Count	45
Aromatic Bond Count	6

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Chemical Component Summary
Name	COCAINE
Systematic Name (OpenEye OEToolkits)	methyl (1R,2R,3S,5S,8S)-8-methyl-3-(phenylcarbonyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
Formula	C₁₇ H₂₁ N O₄
Molecular Weight	303.353
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(OC)C3C1N(C)C(CC1)CC3OC(=O)c2ccccc2
SMILES	CACTVS	3.341	COC(=O)[CH]1[CH](C[CH]2CC[CH]1N2C)OC(=O)c3ccccc3
SMILES	OpenEye OEToolkits	1.5.0	CN1C2CCC1C(C(C2)OC(=O)c3ccccc3)C(=O)OC
Canonical SMILES	CACTVS	3.341	COC(=O)[C@H]1[C@H](C[C@@H]2CC[C@H]1N2C)OC(=O)c3ccccc3
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[N@]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)OC
InChI	InChI	1.03	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
InChIKey	InChI	1.03	ZPUCINDJVBIVPJ-LJISPDSOSA-N

Drug Info: DrugBank

DrugBank ID	DB00907
Name	Cocaine
Groups	approved illicit
Description	An alkaloid ester extracted from the leaves of plants including coca. It 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.
Synonyms	Cocaina Cocaine hydrochloride L-Cocain [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester 2-methyl-3β-hydroxy-1αH,5αH-tropane-2β-carboxylate benzoate (ester) Cocain Cocainum methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate beta-Cocain (−)-cocaine Benzoylmethylecgonine (-)-Cocaine Cocaine L-Cocaine Kokain Neurocaine Methyl benzoylecgonine
Brand Names	PMS-cocaine Hydrochloride Topical Sol 10% PMS-cocaine Hydrochloride Topical Sol 4% Numbrino Cocaine Hydrochloride Nasal Cocaine Hydrochloride Goprelto Cocaine Hydrochloride Topical Sol 10% Cocaine Hydrochloride Top Sol 40mg/ml
Indication	For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
Categories	Agents producing tachycardia Agents that reduce seizure threshold Alkaloids Analgesics and Anesthetics Anesthetics Anesthetics, Local Anticholinergic Agents Aza Compounds Azabicyclo Compounds Cardiovascular Agents Central Nervous System Agents Central Nervous System Stimulants Cholinesterase substrates Cocaine, antagonists & inhibitors Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dopamine Agents Dopamine Uptake Inhibitors Esters of Benzoic Acid Highest Risk QTc-Prolonging Agents Local Anesthetics (Ester) Membrane Transport Modulators Muscarinic Antagonists Nervous System Neurotransmitter Agents Neurotransmitter Uptake Inhibitors OCT2 Inhibitors Ophthalmologicals QTc Prolonging Agents Sensory Organs Sensory System Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Throat Preparations Tropanes Vasoconstrictor Agents
ATC-Code	S01HA01 S02DA02 N01BC01 R02AD03
CAS number	50-36-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium-dependent dopamine transporter	MSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...	unknown	inhibitor
Sodium-dependent noradrenaline transporter	MLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...	unknown	inhibitor
Sodium channel protein	MEQTVLVPPGPDSFNFFTRESLAAIERRIAEEKAKNPKPDKKDDDENGPK...	unknown	inhibitor
Sodium-dependent serotonin transporter	METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...	unknown	inhibitor
Muscarinic acetylcholine receptor M1	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	antagonist
Muscarinic acetylcholine receptor M2	MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...	unknown	antagonist
Sigma non-opioid intracellular receptor 1	MQWAVGRRWAWAALLLAVAAVLTQVVWLWLGTQSFVFQREEIAQLARQYA...	unknown	agonist
Liver carboxylesterase 1	MWLRAFILATLSASAAWGHPSSPPVVDTVHGKVLGKFVSLEGFAQPVAIF...	unknown	binder
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	downregulator
Cholinesterase	MHSKVTIICIRFLFWFLLLCMLIGKSHTEDDIIIATKNGKVRGMNLTVFG...	unknown	substrate
Liver carboxylesterase 1	MWLRAFILATLSASAAWGHPSSPPVVDTVHGKVLGKFVSLEGFAQPVAIF...	unknown	substrate
alpha1-acid glycoprotein	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	binder
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Sodium-dependent dopamine transporter	MSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682