Compound Detail

CHEMBL193

NIFEDIPINE

💊 Approved Drug

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💊 Approved Drug

COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1ccccc1[N+](=O)[O-]

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL193
Name	NIFEDIPINE
Phase	Approved
Structure Type	MOL
InChI Key	HYIMSNHJOBLJNT-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Adalat Adalat a.r. Adalat cc Adalat ic Adalat la 20 Adalat la 30 Adalat la 60 Adalat ret Adalate lp Adanif xl Adipine mr 10 Adipine mr 20 +18 more

Targets

227

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

346.3

MW (Da)

2.18

ALogP

HBA

HBD

107.8

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1981
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-dipine; -pine
USAN Year	1973

Extended Properties

Molecular Formula	C17H18N2O6
MW	346.34
Aromatic Rings	1
Heavy Atoms	25
NP-Likeness	-0.72

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Voltage-gated L-type calcium channel blocker	BLOCKER	Voltage-gated L-type calcium channel	✓	✓

Indications

Cardiovascular Diseases Coronary Vasospasm Hypertension Diabetic Nephropathies Hypertension, Pulmonary Kidney Calculi Myocardial Ischemia Placenta Previa Pre-Eclampsia Premature Birth Raynaud Disease Anus Diseases Epilepsies, Partial Epilepsy Fissure in Ano Proteinuria Renal Insufficiency, Chronic Adrenal Hyperplasia, Congenital Substance-Related Disorders

ATC Classification

C08CA05

nifedipine

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CALCIUM CHANNEL BLOCKERS

C08CA55

nifedipine, combinations

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 160 meas. best 9.3

Ki 38 meas. best 9.28

EC50 23 meas. best 9.0

Kd 6 meas. best 9.83

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Rattus norvegicus CHEMBL376	Kd	9.83	7.375	0.1	2
Oryctolagus cuniculus CHEMBL374	Kd	9.8	9.8	0.2	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL1940	Kd	9.4	9.4	0.4	1
Oryctolagus cuniculus CHEMBL374	IC50	9.3	8.1413	0.5	8
Translocator protein CHEMBL4552	IC50	9.3	9.3	0.5	1
Unchecked CHEMBL612545	Ki	9.28	7.6773	0.5	15
Unchecked CHEMBL612545	IC50	9.08	7.2492	0.8	26
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2830	IC50	9.0	8.77	1.0	2
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL1940	Ki	9.0	9.0	1.0	1
Unchecked CHEMBL612545	EC50	9.0	7.14	1.0	3
Rattus norvegicus CHEMBL376	IC50	8.94	8.4257	1.2	14
Voltage-dependent L-type calcium channel subunit alpha-1D CHEMBL4132	Ki	8.92	8.92	1.2	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	8.85	8.85	1.4	1
Ileum CHEMBL613680	IC50	8.82	8.16	1.5	3
Ileum CHEMBL613680	EC50	8.82	8.82	1.5	1
Voltage-gated L-type calcium channel CHEMBL2095177	IC50	8.78	7.8188	1.6	8
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	8.59	7.2417	2.6	6
Voltage-dependent L-type calcium channel subunit alpha-1D CHEMBL4132	IC50	8.57	8.57	2.7	1
Aorta CHEMBL613606	IC50	8.54	7.9867	2.9	3
Rattus norvegicus CHEMBL376	EC50	8.49	8.49	3.2	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	Ki	8.46	8.46	3.5	1
Sus scrofa CHEMBL613488	IC50	8.44	8.44	3.6	1
Cavia porcellus CHEMBL369	IC50	8.4	7.0709	4.0	11
Voltage-gated L-type calcium channel CHEMBL2095177	Ki	8.33	8.33	4.7	1
Cavia porcellus CHEMBL369	EC50	8.29	8.29	5.1	1
Aorta CHEMBL613672	IC50	8.05	8.05	9.0	5
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	8.0	6.6267	10.0	3
Voltage-gated L-type calcium channel CHEMBL2095177	EC50	7.92	7.92	12.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	Ki	7.84	7.83	14.4	2
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL1940	IC50	7.66	7.4067	22.0	3
Aorta CHEMBL613606	EC50	7.52	6.445	30.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.41	6.995	39.0	4
Right atrium CHEMBL2367363	EC50	7.41	7.41	39.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.02	7.02	96.0	1
Left atrium CHEMBL2367407	EC50	6.58	6.58	260.0	3
Cytochrome P450 1A2 CHEMBL3356	IC50	6.52	6.08	300.0	2
Transient receptor potential cation channel subfamily A member 1 CHEMBL1075310	EC50	6.4	6.4	400.0	1
C-C chemokine receptor type 2 CHEMBL4015	Ki	6.07	6.07	847.0	1
C6-BU-1 CHEMBL614532	IC50	6.0	6.0	1000.0	1
Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1 CHEMBL2097170	IC50	5.95	5.475	1120.0	2
Cholinesterase CHEMBL5763	Ki	5.92	5.61	1200.0	2
L-type calcium channel CHEMBL3988632	IC50	5.92	5.92	1200.0	1
Voltage-dependent L-type calcium channel subunit alpha-1D CHEMBL4138	IC50	5.87	5.87	1350.0	1
Indoleamine 2,3-dioxygenase 2 CHEMBL2189159	IC50	5.82	5.82	1500.0	1
Calvarial osteoblast CHEMBL4296516	EC50	5.81	5.81	1540.0	1
Myosin light chain kinase, smooth muscle CHEMBL2428	IC50	5.7	5.7	2020.0	1
C-C chemokine receptor type 2 CHEMBL4015	IC50	5.66	5.66	2191.0	1
Adenosine receptor A1 CHEMBL318	Ki	5.54	5.54	2890.0	2
Unchecked CHEMBL612545	Kd	5.54	5.54	2900.0	1
Cytochrome P450 2J2 CHEMBL3491	IC50	5.51	5.51	3060.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1204.92	ng.hr.mL-1	Homo sapiens
CL	8.4	mL.min-1.kg-1	-
CL	7.8	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	4.5	mL.min-1.kg-1	Rattus norvegicus
CL	7.0	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	10.0	mL.min-1.kg-1	Macaca
CL	12.3	mL.min-1.kg-1	Canis lupus familiaris
CL	149.1	mL.min-1.g-1	Homo sapiens
CL	22.39	uL.min-1.(10^6cells)-1	Homo sapiens
CL	150.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	150.0	mL.min-1.g-1	Homo sapiens
CL	196.0	mL.min-1.kg-1	Homo sapiens
CL	17.1	uL.min-1.(10^6cells)-1	Homo sapiens
CL	28.7	uL.min-1.(10^6cells)-1	Homo sapiens
CL	8.1	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	175.0	mL.min-1.kg-1	Homo sapiens
Cmax	271.0	nM	Homo sapiens
F	79.0	%	Homo sapiens
F	50.0	%	Homo sapiens
Fu	0.04	-	-
Fu	0.023	-	-
Fu	0.04	-	Homo sapiens
Fu	0.044	-	Homo sapiens
Fu	0.044	-	Homo sapiens
Fu	0.068	-	Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Rattus norvegicus	Kd	=	0.1479	nM	9.83	Inhibition of calcium activation was assessed against calcium-induced constricti...	2002473
Oryctolagus cuniculus	Kd	=	0.1585	nM	9.8	Calcium channel-blocking activity by determined by ability to antagonize calcium...	1920352
Voltage-dependent L-type calcium channel subunit alpha-1C	Kd	=	0.4	nM	9.4	Displacement of [3H]nitrendipine from dihydropyridine receptor of guinea pig myo...	7837222
Translocator protein	IC50	=	0.5	nM	9.3	Inhibition of rat TSPO	38295689
Oryctolagus cuniculus	IC50	=	0.5	nM	9.3	Compound was tested for ability to relax potassium-contracted rabbit aorta smoot...	2834556
Unchecked	Ki	=	0.53	nM	9.28	The compound was tested in vitro for its ability to displace [3H]PN-200-110 from...	-
Unchecked	Ki	=	0.53	nM	9.28	[Ca2+] channel binding affinity was evaluated by its ability to displace [3H]-PN...	-
Unchecked	IC50	=	0.8318	nM	9.08	Compound was tested for its antagonist activity against calcium channel	2846838
Voltage-dependent L-type calcium channel subunit alpha-1C	Ki	=	1.0	nM	9.0	Inhibition of [3H]nitrendipine binding to L-type calcium channel dihydropyridine...	2435904
Unchecked	EC50	=	1.0	nM	9.0	Displacement of [3H]nitrendipine from voltage-dependent calcium channel in rat b...	18640843
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	1.0	nM	9.0	Inhibition of [3H]nitrendipine binding to calcium channels in Rabbit cardiac mus...	3184128
Oryctolagus cuniculus	IC50	=	1.0	nM	9.0	Calcium channel blocking activity in rabbit	2435903
Unchecked	IC50	=	1.07	nM	8.97	Antagonist activity at calcium channel in guinea pig ileum assessed as inhibitio...	19162489
Rattus norvegicus	IC50	=	1.16	nM	8.94	Molar concentration required to block [Ca2+] induced contraction of K+ depolariz...	1552511
Voltage-dependent L-type calcium channel subunit alpha-1D	Ki	=	1.2	nM	8.92	Binding affinity for L-type [Ca2+] channels was measured through displacement of...	9876109
Rattus norvegicus	IC50	=	1.2	nM	8.92	Inhibition of [Ca2+] induced contraction of K+ depolarized rat aorta by 50%	8496910
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	1.42	nM	8.85	Inhibition of rat Cav1.2 channel in rat mesenteric artery assessed as relaxation...	24754640
Unchecked	Ki	=	1.479	nM	8.83	Displacement of (+)-[5-methyl-3H]PN200-100 from L type calcium channel in guinea...	18303827
Unchecked	Ki	=	1.5	nM	8.82	Displacement of [3H]-PN200-110 from L-type calcium channel in Hartley guinea pig...	23586669
Ileum	EC50	=	1.5	nM	8.82	Inhibition of calcium-induced contraction in K+-depolarized guinea pig ileum	30530190

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1384
-	10.6019/CHEMBL3885881	Rattus norvegicus	332
-	10.6019/CHEMBL4295262	Unchecked	44
7513748	10.1021/np50104a019	Rattus norvegicus	23
16472241	10.2174/1570163043334794	Hepatotoxicity	18
26385444	10.1016/j.bmc.2015.09.009	Rattus norvegicus	17
19321237	10.1016/j.ejmech.2009.02.021	Rattus norvegicus	16
-	10.1007/s00044-011-9600-x	Voltage-gated L-type calcium channel	16
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
23586669	10.1021/jm301839q	Unchecked	12
20813434	10.1016/j.ejmech.2010.08.022	Rattus norvegicus	12
2066997	10.1021/jm00111a047	Oryctolagus cuniculus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
31408333	10.1021/acs.jmedchem.9b00708	Rattus norvegicus	11
18303827	10.1021/jm070681+	Unchecked	10
8496700	10.1021/np50094a001	Unchecked	10
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	9
16621936	10.1124/dmd.105.006619	ADMET	8
20070106	10.1021/jm901371v	Homo sapiens	8
3172124	10.1021/jm00118a004	Oryctolagus cuniculus	8

Data from ChEMBL 36 via Core Engine