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Compound Detail

CHEMBL529437

COCAINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
COC(=O)[C@H]1[C@@H](OC(=O)c2ccccc2)C[C@@H]2CC[C@H]1N2C.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL529437
Name COCAINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key PIQVDUKEQYOJNR-VZXSFKIWSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL370805
Active Moiety CHEMBL370805

Known Names

Cocaine hcl Cocaine hydrochloride Cocaine hydrochloride cii Cocaine muriate Cocainum muriaticum Goprelto MCV 4526 NIH 8211 NSC-25263 Numbrino RX-0041-002
6
Targets
13
Activities
2
Assay Types
0
PK Parameters
18
Publications
11
Known Names
2
Indications
1
Mechanisms

Molecular Properties

303.4
MW (Da)
1.87
ALogP
5
HBA
0
HBD
55.8
PSA (Ų)
0.80
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Black Box Warning
USAN Stem -caine

Extended Properties

Molecular Formula C17H22ClNO4
MW 339.82
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 0.93

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium channel alpha subunit blocker BLOCKER Sodium channel alpha subunit ✓ ✓

Indications

Anesthesia Cocaine-Related Disorders

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

Ki 8 meas. best 7.33
IC50 5 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.33 7.33 46.3 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.05 6.7733 89.1 3
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 7.02 7.02 95.0 2
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 6.81 6.81 156.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.51 6.51 306.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 6.39 6.39 404.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.2 6.2 630.0 1
Norepinephrine transporter
CHEMBL304
 Ki 5.71 5.71 1930.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.7 5.7 1990.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 46.3 nM 7.33 Displacement of [125I]RTI55 from human DAT 20597489
Sodium-dependent dopamine transporter IC50 = 89.1 nM 7.05 Displacement of [3H]WIN-35428 from DAT 18556210
Sodium-dependent dopamine transporter IC50 = 89.1 nM 7.05 Displacement of [3H]WIN-35428 from DAT 19053748
Sodium-dependent serotonin transporter Ki = 95.0 nM 7.02 Displacement of [3H]paroxetine from 5HTT 18556210
Sodium-dependent serotonin transporter Ki = 95.0 nM 7.02 Displacement of [3H]paroxetine from 5HTT 19053748
Sodium-dependent dopamine transporter Ki = 156.0 nM 6.81 Displacement of [3H]WIN-35428 from DAT in Sprague-Dawley rat striatum 17489581
Sodium-dependent serotonin transporter Ki = 306.0 nM 6.51 Displacement of [3H]citalopram from 5HTT in Sprague-Dawley rat cerebrum 17489581
Sodium-dependent dopamine transporter IC50 = 404.0 nM 6.39 Inhibition of [3H]DA uptake at DAT in Sprague-Dawley rat striatum 17489581
Sodium-dependent dopamine transporter IC50 = 600.0 nM 6.22 Inhibition of the Dopamine transporter (DAT, SLC6A3) as assessed by GPCR-mediate... 33446713
Sodium-dependent noradrenaline transporter IC50 = 630.0 nM 6.2 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854
Norepinephrine transporter Ki = 1930.0 nM 5.71 Displacement of [3H]nisoxetine from NET in Sprague-Dawley rat cortical tissue 17489581
Sodium-dependent noradrenaline transporter Ki = 1990.0 nM 5.7 Displacement of [3H]nisoxetine from NET 18556210
Sodium-dependent noradrenaline transporter Ki = 1990.0 nM 5.7 Displacement of [3H]nisoxetine from NET 19053748

Literature References

PubMed DOI Target Context # Activities
19053748 10.1021/jm801162z Unchecked 2
17489581 10.1021/jm061354p Sodium-dependent dopamine transporter 2
19053748 10.1021/jm801162z Sodium-dependent dopamine transporter 1
33446713 10.1038/s41598-020-79218-w Sodium-dependent dopamine transporter 1
34112854 10.1038/s41598-021-91700-7 Sodium-dependent noradrenaline transporter 1
20597489 10.1021/jm100269c Sodium-dependent noradrenaline transporter 1
20597489 10.1021/jm100269c Sodium-dependent serotonin transporter 1
20597489 10.1021/jm100269c Sodium-dependent dopamine transporter 1
19053748 10.1021/jm801162z Sodium-dependent noradrenaline transporter 1
19053748 10.1021/jm801162z Sodium-dependent serotonin transporter 1
18556210 10.1016/j.bmc.2008.05.073 Sodium-dependent serotonin transporter 1
18556210 10.1016/j.bmc.2008.05.073 Sodium-dependent noradrenaline transporter 1
18556210 10.1016/j.bmc.2008.05.073 Sodium-dependent dopamine transporter 1
17489581 10.1021/jm061354p Monoamine transporters; Norepinephrine & serotonin 1
17489581 10.1021/jm061354p Monoamine transporters; Norepininephrine & dopamine 1
17489581 10.1021/jm061354p Monoamine transporters; serotonin & dopamine 1
17489581 10.1021/jm061354p Sodium-dependent serotonin transporter 1
17489581 10.1021/jm061354p Norepinephrine transporter 1

Data from ChEMBL 36 via Core Engine