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Drug-Target Interaction

Drug

show drug details
PubChem ID:2520
Structure:
Synonyms:
(+)-verapamil
(+-)-Verapamil
(1)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile
152-11-4 (HYDROCHLORIDE SALT)
2-(3,4-Dimethoxyphenyl)-5-((2-(3,4-dimethoxyphenyl)ethyl)(methyl)amino)-2-isopropylpentanenitrile, (+/-)-
2-(3,4-Dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methyl-amino]-2-(1-methylethyl) pentanenitrile
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropy
5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
52-53-9
52-53-9 (FREE BASE)
56949-77-0
AB00053495
AIDS-002990
AIDS002990
alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)-methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-
Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
Bio1_000425
Bio1_000914
Bio1_001403
Bio2_000233
Bio2_000713
BPBio1_000268
BSPBio_000242
BSPBio_001513
BSPBio_002358
C07188
C27H38N2O4
Calan
Calcan
Cardibeltin
CCRIS 6749
CHEBI:9948
cMAP_000023
Cordilox
Covera-HS
CP-16533-1
D-365
D02356
DB00661
Dexverapamil
Dilacoran
DivK1c_000399
EINECS 200-145-1
EINECS 260-462-6
Falicard
Finoptin
IDI1_000399
IDI1_033983
Iproveratril
Isoptimo
Isoptin
Isoptine
Isotopin
Izoptin
KBio1_000399
KBio2_000233
KBio2_002343
KBio2_002801
KBio2_004911
KBio2_005369
KBio2_007479
KBio3_000465
KBio3_000466
KBio3_002823
KBioGR_000233
KBioGR_001372
KBioGR_002343
KBioSS_000233
KBioSS_002346
Lopac0_001237
LS-174
Manidon
NCGC00024710-04
NCGC00024710-05
NCGC00024710-06
NCGC00024710-07
NCGC00024710-08
NCGC00024710-09
nchembio.79-comp5
NCI60_020143
NINDS_000399
NSC 135784
NSC272366 (HYDROCHLORIDE SALT)
NSC657799 (HYDROCHLORIDE SALT)
Prestwick0_000141
Prestwick1_000141
Prestwick2_000141
Prestwick3_000141
SPBio_001820
SPBio_002181
Spectrum2_001740
Spectrum4_000906
Spectrum5_001786
STOCK2S-60963
Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
Vasolan
Verapamil
Verapamil (USAN/INN)
Verapamil HCl
Verapamil hydrochloride
Verapamil [USAN:BAN:INN]
Verapamil [USAN:INN:BAN]
Verapamilo
Verapamilo [INN-Spanish]
Verapamilum
Verapamilum [INN-Latin]
Verelan
ATC-Codes:
Side-Effects:
Side-EffectFrequency
infection0.08866667
constipation0.062083334
upper respiratory infection0.054
headache0.03883334
flu syndrome0.03375
peripheral edema0.03275
dizziness0.030919995
rhinitis0.027
sinusitis0.02675
pharyngitis0.02675
dyspepsia0.024666667
pain0.024
diarrhea0.024
nausea0.0226
hypotension0.020352943
fatigue0.02021429
asthenia0.02
ecg abnormal0.02
edema0.017708331
pulmonary edema0.017000003
hypertension0.017
rash0.014333334
elevated liver enzymes0.014
dyspnea0.014
ankle edema0.014
bradycardia0.0139999995
av block0.011777779
myalgia0.011
paresthesia0.01
flushing0.0064000003
postural hypotension0.0040
paralysis0.0010
gynecomastia0
sweating0
palpitations0
ecchymosis0
muscle cramps0
urinary frequency0
heart failure0
bronchospasm0
cardiomyopathy0
vasculitis0
allergic reaction0
hepatitis0
somnolence0
erythema multiforme0
depressive symptoms0
hyperkeratosis0
increased sweating0
arthralgia0
oligomenorrhea0
insomnia0
abnormal vision0
vomiting0
ihss0
respiratory failure0
angioedema0
galactorrhea0
tremor0
anaphylaxis0
claudication0
chest pain0
jaundice0
paralytic ileus0
dry mouth0
urticaria0
pruritus0
muscle weakness0
stevens - johnson syndrome0
confusion0
myocardial infarction0
sinus arrest0
syncope0
alopecia0
cerebrovascular accident0
spasm0
seizures0
nystagmus0
tinnitus0
vertigo0
impotence0
hypersensitivity0
hyperprolactinemia0
purpura0
blurred vision0
numbness0
diplopia0

Target

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Uniprot ID:CP2C9_HUMAN
Synonyms:
(R)-limonene 6-monooxygenase
(S)-limonene 6-monooxygenase
(S)-limonene 7-monooxygenase
CYPIIC9
Cytochrome P450 2C9
P-450MP
P450 MP-4/MP-8
P450 PB-1
S-mephenytoin 4-hydroxylase
EC-Numbers:1.14.13.48
1.14.13.49
1.14.13.80
Organism:Homo sapiens
Human
PDB IDs:1OG2 1OG5 1R9O
Structure:
1R9O

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----
----
----
----

References:

10640508
Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A.. B Ma; T Prueksaritanont; J H Lin (2000) Drug metabolism and disposition: the biological fate of chemicals display abstract
The inhibitory effects of six commonly used calcium channel blockers on three major cytochrome P-450 activities were examined and characterized in human liver microsomes. All six compounds reversibly inhibited CYP2D6 (bufuralol 1'-hydroxylation) and CYP2C9 (tolbutamide methyl hydroxylation) activities. The IC(50) values for the inhibition of CYP2D6 and CYP2C9 for nicardipine were 3 to 9 microM, whereas those for all others ranged from 14 to >150 microM. Except for nifedipine, all calcium channel blockers showed increased inhibitory potency toward CYP3A activities (testosterone 6beta-hydroxylation and midazolam 1'-hydroxylation) after 30-min preincubation with NADPH. IC(50) values for the inhibition of testosterone 6beta-hydroxylase obtained in the NADPH-preincubation experiment for nicardipine (1 microM), verapamil (2 microM), and diltiazem (5 microM) were within 10-fold, whereas those for amlodipine (5 microM) and felodipine (13 microM) were >200-fold of their respective plasma concentrations reported after therapeutic doses. Similar results also were obtained based on midazolam 1'-hydroxylase activity. Unlike the observations with mibefradil, a potent irreversible inhibitor of CYP3A, the NADPH-dependent inhibition of CYP3A activity by nicardipine and verapamil was completely reversible on dialysis, whereas that by diltiazem was partially restored (80%). Additional experiments revealed that nicardipine, verapamil, and diltiazem formed cytochrome P-450-iron (II)-metabolite complex in both human liver microsomes and recombinant CYP3A4. Nicardipine yielded a higher extent of complex formation ( approximately 30% at 100 microM), and was a much faster-acting inhibitor (maximal inhibition rate constant approximately 2 min(-1)) as compared with verapamil and diltiazem. These present findings that the CYP3A inhibition caused by nicardipine, verapamil, and diltiazem is, at least in part, quasi-irreversible provide a rational basis for pharmacokinetically significant interactions reported when they were coadministered with agents that are cleared primarily by CYP3A-mediated pathways.
12396893
16278191
8750925