Compound Detail

CHEMBL370805

COCAINE

💊 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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL370805
Name	COCAINE
Phase	Approved
Structure Type	MOL
InChI Key	ZPUCINDJVBIVPJ-LJISPDSOSA-N
Therapeutic	✓ Yes

Known Names

(r)-(-)-cocaine Benzoylmethylecgonine Cocaine Cocainum IDS-NC-004 Neurocaine RX-0041 RX0041

Targets

481

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

303.4

MW (Da)

1.87

ALogP

HBA

HBD

55.8

PSA (Å²)

0.80

QED

Ro5 Violations

Rot. Bonds

Drug Information

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

Routes of Administration

Topical

Flags

Black Box Warning Natural Product

USAN Stem

-caine

Extended Properties

Molecular Formula	C17H21NO4
MW	303.36
Aromatic Rings	1
Heavy Atoms	22
NP-Likeness	0.93

Indications

Cocaine-Related Disorders Cocaine-Related Disorders Opioid-Related Disorders Hypersensitivity Substance Withdrawal Syndrome

ATC Classification

N01BC01

cocaine

Level 1: NERVOUS SYSTEM

Level 2: ANESTHETICS

R02AD03

cocaine

Level 1: RESPIRATORY SYSTEM

Level 2: THROAT PREPARATIONS

S01HA01

cocaine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

S02DA02

cocaine

Level 1: SENSORY ORGANS

Level 2: OTOLOGICALS

Activity Summary

IC50 251 meas. best 9.3

Ki 228 meas. best 8.46

Kd 2 meas. best 8.36

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent serotonin transporter CHEMBL313	IC50	9.3	6.2379	0.5	29
Monoclonal antibody (mAb) 2E2 CHEMBL612442	Ki	8.46	8.46	3.5	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.36	5.71	4.4	6
Monoclonal antibody (mAb) 2E2 CHEMBL612442	Kd	8.36	8.36	4.4	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	7.5	6.6788	32.0	59
Sodium-dependent dopamine transporter CHEMBL238	Ki	7.5	6.4678	32.0	32
Sodium-dependent serotonin transporter CHEMBL313	Ki	7.35	6.7663	45.0	30
Sodium-dependent serotonin transporter CHEMBL228	Ki	7.35	6.5562	45.0	29
Sodium-dependent dopamine transporter CHEMBL2986	IC50	7.19	7.025	65.0	2
Sodium-dependent dopamine transporter CHEMBL338	IC50	7.18	6.6701	66.0	77
Monkey CHEMBL614874	IC50	7.16	7.16	70.0	1
Unchecked CHEMBL612545	IC50	7.05	5.782	89.1	5
Sodium-dependent dopamine transporter CHEMBL238	IC50	7.05	6.544	89.1	35
Sodium-dependent dopamine transporter CHEMBL5032	IC50	7.02	7.02	95.6	1
Rattus norvegicus CHEMBL376	Ki	6.97	6.6383	108.0	6
Norepinephrine transporter CHEMBL304	Ki	6.97	6.4436	108.0	25
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.97	5.9289	108.0	28
Rattus norvegicus CHEMBL376	IC50	6.9	6.5037	127.0	19
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.75	6.3724	180.0	25
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.73	6.1773	186.0	22
Sodium-dependent dopamine transporter CHEMBL2799	IC50	6.7	6.7	200.0	1
Unchecked CHEMBL612545	Ki	6.64	5.8988	230.0	8
Sodium-dependent dopamine transporter CHEMBL2799	Ki	6.07	6.07	850.0	1
Bos taurus CHEMBL613489	IC50	6.07	6.07	843.0	1
Norepinephrine transporter CHEMBL304	IC50	5.6	5.4735	2500.0	23
Transporter CHEMBL6184	Ki	5.5	5.49	3192.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.05	5.05	8830.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	4.31	4.31	49000.0	1
Muscarinic acetylcholine receptor M1 CHEMBL276	Ki	4.21	4.21	61397.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	32.0	mL.min-1.kg-1	Homo sapiens
CL	64.0	mL.min-1.kg-1	Macaca
CL	102.0	mL.min-1.kg-1	Canis lupus familiaris
CL	260.0	mL.min-1.kg-1	Rattus norvegicus
CL	32.0	mL.min-1.kg-1	Homo sapiens
CL	32.0	mL.min-1.kg-1	Homo sapiens
Fu	0.09	-	-
Fu	0.018	-	-
Fu	0.09	-	Homo sapiens
Fu	0.12	-	Homo sapiens
MRT	1.0	hr	Homo sapiens
T1/2	0.76	hr	Homo sapiens
T1/2	0.3333	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent serotonin transporter	IC50	=	0.5	nM	9.3	Displacement of [3H]paroxetine from Serotonin transporter of rat caudate putamen	15857139
Monoclonal antibody (mAb) 2E2	Ki	=	3.5	nM	8.46	Binding affinity towards human monoclonal antibody 2E2 using [3H]cocaine	14695827
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	4.4	nM	8.36	K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv1...	12190308
Monoclonal antibody (mAb) 2E2	Kd	=	4.4	nM	8.36	Dissociation Constant for human monoclonal antibody 2E2 with [3H]cocaine	14695827
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Displacement of [3H]WIN-35428 from dopamine transporter in rat caudate putamen t...	9435910
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Binding affinity towards dopamine transporter using [3H]WIN-35428 as radioligand...	9632375
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Affinity for rat dopamine transporter using [3H]WIN-35428 displacement.	7562926
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Affinity for dopamine transporter was assessed by the ability to displace [3H]WI...	11881989
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Binding affinity was determined against cocaine receptor by measuring the abilit...	7966147
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Binding affinity against dopamine transporter in rat caudate putamen tissue usin...	8941387
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Displacement of [3H]WIN-35428 from dopamine transporter (DAT) in Rat Caudate Put...	9083474
Sodium-dependent dopamine transporter	Ki	=	32.0	nM	7.5	Binding affinity towards dopamine transporter using [3H]WIN-35428 as radioligand...	8691489
Sodium-dependent serotonin transporter	Ki	=	45.0	nM	7.35	Binding affinity towards serotonin transporter 5-HTT was determined using [3H]pa...	14711303
Sodium-dependent serotonin transporter	Ki	=	45.0	nM	7.35	Displacement of [3H]paroxetine from human 5HTT	16854064
Sodium-dependent serotonin transporter	Ki	=	45.0	nM	7.35	Displacement of [3H]paroxetine from 5HTT	15566309
Sodium-dependent serotonin transporter	Ki	=	45.0	nM	7.35	Displacement of [3H]paroxetine from 5HTT	16279803
Sodium-dependent dopamine transporter	IC50	=	65.0	nM	7.19	In vitro inhibitory activity towards [3H]cocaine binding to rat striatal tissue	1995895
Sodium-dependent dopamine transporter	IC50	=	66.0	nM	7.18	Inhibition of [125I]RTI-55 cocaine binding to the dopamine transporter.	1552510
Sodium-dependent dopamine transporter	IC50	=	67.8	nM	7.17	Compound was evaluated for inhibition of specifically bound [3H]- cocaine (2.7 n...	2033595
Monkey	IC50	=	70.0	nM	7.16	Concentration inhibiting [3H]cocaine binding to rat striatal membranes.	1613745

Literature References

PubMed	DOI	Target Context	# Activities
1469704	10.1021/jm00103a015	Rattus norvegicus	32
15566309	10.1021/jm0401311	Mus musculus	21
1613745	10.1021/jm00090a005	ADMET	19
14711303	10.1021/jm030453p	Mus musculus	13
12723940	10.1021/jm030092d	Rattus norvegicus	11
17255098	10.1074/jbc.m610633200	Sodium-dependent dopamine transporter	9
15920768	10.1002/jps.20373	ADMET	8
9526561	10.1021/jm970025h	Sodium-dependent dopamine transporter	7
28319392	10.1021/acs.jmedchem.7b00141	Sodium-dependent dopamine transporter	7
1552510	10.1021/jm00084a001	Sodium-dependent dopamine transporter	6
14711303	10.1021/jm030453p	Rattus norvegicus	6
15566309	10.1021/jm0401311	Rattus norvegicus	6
1588560	10.1021/jm00088a017	Sodium-dependent dopamine transporter	5
8258830	10.1021/jm00077a011	Sodium-dependent dopamine transporter	5
6716406	10.1021/jm00371a023	Mus musculus	5
11229756	10.1016/s0960-894x(00)00703-4	Rattus norvegicus	5
12061889	10.1021/jm0200409	ADMET	5
9599245	10.1021/jm980028+	Sodium-dependent dopamine transporter	4
38117239	10.1021/acs.jmedchem.3c02037	Unchecked	4
10987420	10.1016/s0960-894x(00)00371-1	Unchecked	4

Data from ChEMBL 36 via Core Engine