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Details

Stereochemistry RACEMIC
Molecular Formula C21H26N2O7
Molecular Weight 418.4403
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Nimodipine

SMILES

COCCOC(=O)C1=C(C)NC(C)=C(C1C2=CC(=CC=C2)[N+]([O-])=O)C(=O)OC(C)C

InChI

InChIKey=UIAGMCDKSXEBJQ-UHFFFAOYSA-N
InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3

HIDE SMILES / InChI

Molecular Formula C21H26N2O7
Molecular Weight 418.4403
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Nimodipine is a dihydropyridine calcium antagonist which has been shown to dilate cerebral arterioles and increase cerebral blood flow in animals and humans. It has potential in the treatment of a range of cerebrovascular disorders. Major interest to date, however, has focused on its use in the prevention and treatment of the delayed ischaemic neurological deficits that frequently occur in patients with subarachnoid haemorrhages as a result of sustained cerebral vasospasm. Nimodipine, a Ca2+ antagonist with cerebrovasodilatory and anti-ischemic effects, binds to rat, guinea pig, and human brain membranes with high affinity (less than 1 nM). Only at higher concentrations has nimodipine been reported to block the release of some neurotransmitters and hormones from neuronal tissue.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.27 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NIMOTOP
Primary
NYMALIZE
Primary
NIMODIPINE

Cmax

ValueDoseCo-administeredAnalytePopulation
29 ng/mL
60 mg single, oral
NIMODIPINE plasma
Homo sapiens
20 nM
100 mg single, oral
NIMODIPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
47.6 ng × h/mL
60 mg single, oral
NIMODIPINE plasma
Homo sapiens
100 nM × h
100 mg single, oral
NIMODIPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.27 h
60 mg single, oral
NIMODIPINE plasma
Homo sapiens
2.2 h
100 mg single, oral
NIMODIPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
NIMODIPINE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Nimodipine is given orally in the form of soft gelatin 30 mg capsules for subarachnoid hemorrhage. The recommended oral dose is 60 mg (two 30 mg capsules) every 4 hours for 21 consecutive days.
Route of Administration: Oral
In Vitro Use Guide
Nimodipine (1-100 μM) conferred 65±13% neuroprotection in PC12 neuronal cultures upon exposure to oxygen-glucose deprivation (OGD) and 35±6% neuroprotection towards different trophic withdrawal-induced cell death measured by lactate dehydrogenase and caspase 3 activities. The time window of nimodipine conferred neuroprotection was detected during the first 5h but not at longer OGD exposures.
Substance Class Chemical
Record UNII
57WA9QZ5WH
Record Status Validated (UNII)
Record Version