Compound Detail

CHEMBL6966

VERAPAMIL

💊 Approved Drug

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💊 Approved Drug

COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL6966
Name	VERAPAMIL
Phase	Approved
Structure Type	MOL
InChI Key	SGTNSNPWRIOYBX-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

CP-16,533-1 CP-165331 D-365 Iproveratril NSC-272306NA Verapamil Verapamil slow release Verapamilo

Targets

498

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

454.6

MW (Da)

5.09

ALogP

HBA

HBD

64.0

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1981
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Stem	-pamil
USAN Year	1968

Extended Properties

Molecular Formula	C27H38N2O4
MW	454.61
Aromatic Rings	2
Heavy Atoms	33
NP-Likeness	-0.07

Indications

Cardiovascular Diseases Arrhythmias, Cardiac Arrhythmias, Cardiac Atrial Fibrillation Bipolar Disorder Diabetes Mellitus, Type 1 Heart Failure Pain Severe Acute Respiratory Syndrome Crohn Disease Diabetes Mellitus, Type 2 Hodgkin Disease Ischemic Stroke Osteoarthritis, Knee Respiratory Syncytial Virus Infections Substance-Related Disorders Hemorrhage

ATC Classification

C08DA01

verapamil

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CALCIUM CHANNEL BLOCKERS

C08DA51

verapamil, combinations

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 387 meas. best 9.6

EC50 74 meas. best 7.51

Ki 32 meas. best 8.85

Kd 5 meas. best 8.16

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Translocator protein CHEMBL4552	IC50	9.6	9.225	0.2	2
MDA-MB-435 CHEMBL614697	IC50	9.6	8.94	0.2	2
MCF7 CHEMBL387	IC50	8.99	6.35	1.0	5
Unchecked CHEMBL612545	IC50	8.88	6.0906	1.3	66
Voltage-gated L-type calcium channel CHEMBL2095177	Ki	8.85	8.85	1.4	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	8.53	6.0238	3.0	90
Voltage-gated L-type calcium channel CHEMBL2095177	IC50	8.43	7.0757	3.7	7
HCT-116 CHEMBL394	IC50	8.4	7.13	4.0	7
K562 CHEMBL385	IC50	8.37	4.75	4.3	8
KB CHEMBL398	IC50	8.36	6.535	4.4	2
KB 3-1 CHEMBL614590	IC50	8.33	6.0133	4.7	3
KBv200 CHEMBL5465447	IC50	8.3	7.76	5.0	4
Rattus norvegicus CHEMBL376	Kd	8.16	8.16	6.9	1
OVCAR-8 CHEMBL612555	IC50	8.07	8.07	8.5	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.0	6.6205	10.0	20
Oryctolagus cuniculus CHEMBL374	Kd	8.0	8.0	10.0	1
Rattus norvegicus CHEMBL376	IC50	8.0	6.998	10.0	5
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.0	5.0889	10.0	19
Cytochrome P450 3A4 CHEMBL340	IC50	7.96	5.2711	11.0	9
Unchecked CHEMBL612545	Ki	7.92	6.1829	12.0	7
A2780/Taxol CHEMBL4483224	IC50	7.73	7.615	18.8	2
Thoracic aorta CHEMBL2367449	EC50	7.51	7.3138	31.0	8
Molecular identity unknown CHEMBL612546	EC50	7.51	7.51	30.9	1
Aorta CHEMBL613606	EC50	7.51	7.1675	31.0	4
Cavia porcellus CHEMBL369	IC50	7.46	6.225	35.0	10
Eca-109/VCR CHEMBL6066735	IC50	7.42	7.42	38.5	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	7.41	7.41	39.0	1
L5178Y CHEMBL614720	IC50	7.32	5.82	47.9	2
Voltage-dependent L-type calcium channel subunit alpha-1S CHEMBL4108	Ki	7.24	7.24	58.0	1
D(3) dopamine receptor CHEMBL234	Ki	7.2	7.2	63.0	1
NCI/ADR-RES CHEMBL613829	IC50	7.16	5.864	69.5	10
Multidrug resistance-associated protein 1 CHEMBL3004	IC50	7.1	5.618	79.0	5
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	7.0	6.3388	100.0	8
KB/VJ300 CHEMBL4513128	IC50	7.0	6.21	100.0	4
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.98	6.98	105.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	EC50	6.92	5.7833	120.0	18
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.9	6.9	126.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.9	6.9	127.0	1
SW-620 CHEMBL612262	IC50	6.85	6.1733	142.0	3
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL1940	IC50	6.82	4.94	150.0	5
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.81	6.81	155.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.78	6.78	165.0	1
NCI-H292 CHEMBL614733	IC50	6.75	6.335	180.0	2
D(3) dopamine receptor CHEMBL234	IC50	6.73	6.73	186.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	6.7	6.7	200.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.66	6.66	217.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.62	6.62	240.0	1
Unchecked CHEMBL612545	EC50	6.61	6.0809	245.0	23
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.53	6.53	297.0	1
Oryctolagus cuniculus CHEMBL374	IC50	6.52	6.52	300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	-	-	Rattus norvegicus
AUC	451.5	ng.hr.mL-1	Rattus norvegicus
AUC	367.0	ng.hr.mL-1	Rattus norvegicus
AUC	256.17	ng.hr.mL-1	Rattus norvegicus
AUC	297.83	ng.hr.mL-1	Rattus norvegicus
AUC	638.5	ng.hr.mL-1	Rattus norvegicus
AUC	692.67	ng.hr.mL-1	Rattus norvegicus
AUC	198.5	ng.hr.mL-1	Rattus norvegicus
AUC	231.83	ng.hr.mL-1	Rattus norvegicus
AUC	7033.17	ng.hr.mL-1	Rattus norvegicus
AUC	1458.0	ng.hr.mL-1	Rattus norvegicus
CL	14.66	mL.min-1.kg-1	Homo sapiens
CL	18.0	mL.min-1.kg-1	Homo sapiens
CL	16.5	mL.min-1.kg-1	Homo sapiens
CL	18.0	mL.min-1.kg-1	Homo sapiens
CL	11.8	mL.min-1.kg-1	Homo sapiens
CL	105.0	mL.min-1.g-1	Homo sapiens
CL	37.1	mL.min-1.kg-1	Macaca
CL	40.4	mL.min-1.kg-1	Rattus norvegicus
CL	62.2	mL.min-1.kg-1	Canis lupus familiaris
CL	13.7	mL.min-1.kg-1	Homo sapiens
CL	18.0	mL.min-1.kg-1	Homo sapiens
CL	763.0	mL.min-1.kg-1	Mus musculus
CL	8.0	mL.min-1.kg-1	Mus musculus
CL	126.0	mL.min-1.kg-1	Homo sapiens
CL	209.0	mL.min-1.g-1	Homo sapiens
CL	-	mL.min-1.g-1	Homo sapiens
CL	649.0	mL.min-1.g-1	Mus musculus
CL	1.0	mL.min-1.g-1	Mus musculus
CL	26.3	uL.min-1.(10^6cells)-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MDA-MB-435	IC50	=	0.25	nM	9.6	Reversal of vinblastine resistance in multidrug resistant MDA435/LCC6 cells by M...	17154505
Translocator protein	IC50	=	0.25	nM	9.6	Inhibition of rat TSPO	38295689
MCF7	IC50	=	1.02	nM	8.99	Reversal of paclitaxel resistance in human MCF7 cells assessed as reduction in p...	39151276
Unchecked	IC50	=	1.31	nM	8.88	Potentiation of vincristine-induced cytotoxicity against human KBV cells assesse...	30455148
Voltage-gated L-type calcium channel	Ki	=	1.4	nM	8.85	Calcium antagonistic activity by measuring [3H]nitrendipine displacement at L-ty...	7473567
Translocator protein	IC50	=	1.4	nM	8.85	Ability to inhibit [3H]-PK 11195 binding to peripheral-type benzodiazepine recep...	8709127
Unchecked	IC50	=	1.593	nM	8.8	Reversal of multidrug resistance activity in P-gp overexpressing human KB-VIN ce...	32750634
Unchecked	IC50	=	1.62	nM	8.79	Reversal of resistance to paclitaxel-induced cytotoxicity in HEK293 cells assess...	33280384
MCF7	IC50	=	2.68	nM	8.57	Reversal of paclitaxel resistance in human MCF7 cells assessed as reduction in p...	39151276
ATP-dependent translocase ABCB1	IC50	=	2.97	nM	8.53	Reversal of P-glycoprotein mediated multidrug resistance in human KBV cells asse...	33360797
Voltage-gated L-type calcium channel	IC50	=	3.7	nM	8.43	Ability to inhibit [3H]nitrendipine binding to the calcium channel receptor(CCR)...	8709127
Voltage-gated L-type calcium channel	IC50	=	3.7	nM	8.43	Inhibition of [3H]nitrendipine binding at L-type [Ca2+] channel in rat cortex ho...	7473567
Unchecked	IC50	=	3.84	nM	8.42	Reversal of resistance to paclitaxel-induced cytotoxicity in human KB 3-1 cells ...	33280384
ATP-dependent translocase ABCB1	IC50	=	3.87	nM	8.41	Inhibition of ABCB1 in human HeLa S3 cells assessed as potentiation of vincristi...	32569926
HCT-116	IC50	=	4.0	nM	8.4	Effect on vinblastine IC50 against MDR human carcinoma HCT116/VM46 cell line at ...	12729663
K562	IC50	=	4.3	nM	8.37	Reversal of vinorelbine resistance in human K562 cells assessed as reduction in ...	36728755
KB	IC50	=	4.4	nM	8.36	Reversal of vinorelbine resistance in human KB cells assessed as reduction in ce...	36728755
Unchecked	IC50	=	4.52	nM	8.35	Potentiation of cisplatin-induced cytotoxicity against human KBV cells assessed ...	35219948
ATP-dependent translocase ABCB1	IC50	=	4.59	nM	8.34	Reversal of P-glycoprotein mediated multidrug resistance in human KBV cells asse...	33360797
KB 3-1	IC50	=	4.7	nM	8.33	Reversal of P-gp-mediated multidrug resistance to Cytotoxicity of colchicine aga...	17488128

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	332
28964936	10.1016/j.ejmech.2017.09.014	Unchecked	162
-	10.5281/zenodo.13943903	ADMET	88
31158845	10.1038/s41586-019-1291-3	ADMET	62
26197353	10.1021/acs.jmedchem.5b00428	Mycobacterium tuberculosis	45
-	10.6019/CHEMBL4295262	Unchecked	44
26562541	10.1016/j.ejmech.2015.10.054	Mycobacterium tuberculosis	42
32569926	10.1016/j.ejmech.2020.112422	ATP-dependent translocase ABCB1	26
14998330	10.1021/jm0303204	Unchecked	26
21135265	10.1124/dmd.110.035642	ADMET	24
31585275	10.1016/j.ejmech.2019.111726	ATP-dependent translocase ABCB1	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
21135265	10.1124/dmd.110.035642	Rattus norvegicus	18
12729663	10.1016/s0960-894x(03)00294-4	HCT-116	17
33706147	10.1016/j.ejmech.2021.113317	Unchecked	16
24949913	10.1021/np500076v	Voltage-gated L-type calcium channel	15
19364853	10.1128/aac.01689-08	Plasmodium falciparum	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
29407947	10.1016/j.ejmech.2018.01.027	Unchecked	14
24602787	10.1016/j.ejmech.2014.02.003	ADMET	14

Data from ChEMBL 36 via Core Engine