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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

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2565839

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

CNS Active
4002
Curator's Comment: Nimodipine has adequate brain penetration, dilates intracranial vessels in animals and humans. Experimental data suggest direct neuronal action of nimodipine in animals. https://www.ncbi.nlm.nih.gov/pubmed/2565839

Originator

Bayer
150
Curator's Comment: # Meyer et al, patented to Bayer AG

Approval Year

1988
90
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.27 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
NIMOTOP

Approved Use

Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured intracranial berry aneurysms regardless of their post-ictus neurological condition (i.e., Hunt and Hess Grades I-V).

Launch Date

1988
Primary
Approved
8583
NYMALIZE

Approved Use

NYMALIZE is a dihydropyridine calcium channel blocker indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in adult patients with subarachnoid hemorrhage (SAH) from ruptured intracranial berry aneurysms regardless of their post-ictus neurological condition (i.e., Hunt and Hess Grades I-V).

Launch Date

2013
Primary
Approved
8583
NIMODIPINE

Approved Use

Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured intracranial berry aneurysms regardless of their post-ictus neurological condition (i.e., Hunt and Hess Grades I-V).

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
29 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7962672
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8249618
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
47.6 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7962672
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
100 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8249618
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.27 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7962672
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8249618
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NIMODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018869s014lbl.pdf
NIMODIPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
BCRP
910
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BCRP
985
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 yes
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7575
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7575
ChemicalBook
CB1398087
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1398087
eMolecules
592477
https://www.emolecules.com/cgi-bin/more?vid=592477
MolPort
MolPort-001-840-190
https://www.molport.com/shop/molecule-link/MolPort-001-840-190
Selleck Chemicals
Nimodipine(Nimotop)
http://www.selleckchem.com/products/Nimodipine(Nimotop).html
PubMed

PubMed

TitleDatePubMed
Effect of nimodipine (Bay e 9736) on postischaemic cerebrovascular reactivity, as revealed by measuring regional cerebral blood flow (rCBF).
1982
Cerebral arterial spasm--a controlled trial of nimodipine in patients with subarachnoid hemorrhage.
1983 Mar 17
Cerebral blood flow and neurologic outcome when nimodipine is given after complete cerebral ischemia in the dog.
1984 Mar
Therapeutic trial of intravenous nimodipine in patients with established cerebral vasospasm after rupture of intracranial aneurysms.
1988 Aug
Effect of oral nimodipine on cerebral infarction and outcome after subarachnoid haemorrhage: British aneurysm nimodipine trial.
1989 Mar 11
Effect of treatment with nimodipine in patients with mild and moderate essential hypertension.
1990 Apr
Nimodipine pretreatment improves cerebral blood flow and reduces brain edema in conscious rats subjected to focal cerebral ischemia.
1990 Nov
Protective effect of nimodipine against ischemic neuronal damage in rat hippocampus without changing postischemic cerebral blood flow.
1990 Sep
Quinine-induced tinnitus in rats.
1991 Oct
Nimodipine reduces the toxicity of intravenous bupivacaine in rats.
1992 Jun
Pulmonary vasoconstriction following intravenous nimodipine.
1992 May
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.
1993 Jul
Hypotensive effect of nimodipine during treatment for aneurysmal subarachnoid haemorrhage.
1995
Dose-finding study with nimodipine: a selective central nervous system calcium channel blocker on aminophylline induced seizure models in rats.
1998 Mar 15
Haloperidol-induced catalepsy is influenced by calcium channel antagonists.
2000 May-Jun
Calcium antagonists decrease capillary wall damage in aging hypertensive rat brain.
2001 Mar-Apr
High initial blood pressure after acute stroke is associated with poor functional outcome.
2001 May
Functional properties of Cav1.3 (alpha1D) L-type Ca2+ channel splice variants expressed by rat brain and neuroendocrine GH3 cells.
2001 Oct 19
Calcium channel blocker, nimodipine, for the treatment of bipolar disorder during pregnancy.
2002 Dec
Cerebral vasospasm after subarachnoid hemorrhage.
2003 Apr
Use of phenytoin and other anticonvulsant prophylaxis in patients with aneurysmal subarachnoid hemorrhage.
2005 Dec
Antioxidant effect of nimodipine in young rats after pilocarpine-induced seizures.
2005 Sep
Ion changes in spreading ischaemia induce rat middle cerebral artery constriction in the absence of NO.
2005 Sep
Effect of nimodipine on outcome in patients with traumatic subarachnoid haemorrhage: a systematic review.
2006 Dec
Reversible cerebral angiopathy: efficacy of nimodipine.
2006 Dec
Low dose hydroxylated PCB induces c-Jun expression in PC12 cells.
2006 Mar
The L-type calcium channel blocker nimodipine mitigates cytoskeletal proteins phosphorylation in dichlorvos-induced delayed neurotoxicity in rats.
2006 May
Protective effect of adenosine reuptake inhibitors in haloperidol-induced orofacial dyskinesia and associated behavioural, biochemical and neurochemical changes.
2007
[Effect of nimodipine on mechanisms of HL-60 cell apoptosis induced by cytarabine].
2007 Feb
L-type calcium channel blockade on haloperidol-induced c-Fos expression in the striatum.
2007 Nov 9
Amphetamine-induced anxiety-related behavior in animal models.
2007 Nov-Dec
Mechanisms of potassium- and capsaicin-induced axonal calcitonin gene-related peptide release: involvement of L- and T-type calcium channels and TRPV1 but not sodium channels.
2008 Feb 6
A number of marketed dihydropyridine calcium channel blockers have mineralocorticoid receptor antagonist activity.
2008 Mar
Ammonia inhibits the C-type natriuretic peptide-dependent cyclic GMP synthesis and calcium accumulation in a rat brain endothelial cell line.
2008 May
Protective effect of L-type calcium channel blockers against haloperidol-induced orofacial dyskinesia: a behavioural, biochemical and neurochemical study.
2008 Sep
Cell death induced by zinc and cadmium is mediated by clusterin in cultured mouse seminiferous tubules.
2009 Jul
Intraarterial nimodipine infusion to treat symptomatic cerebral vasospasm after aneurysmal subarachnoid hemorrhage.
2009 Sep
Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease.
2012 Oct
Nephroprotective effect of calcium channel blockers against toxicity of lead exposure in mice.
2013 Apr 26
Role of voltage gated Ca2+ channels in rat visceral hypersensitivity change induced by 2,4,6-trinitrobenzene sulfonic acid.
2013 Mar 28
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

JP2012500283A
14
JP4722295B2
105
JPH0881361A
1

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.
Name Type Language
Nimodipine
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
ADMON
Preferred Name English
NIMODIPINE [VANDF]
Common Name English
NIMODIPINE [MI]
Common Name English
NIMODIPINE [EP MONOGRAPH]
Common Name English
ISOPROPYL 2-METHOXYETHYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLATE
Systematic Name English
PERIPLUM
Brand Name English
NIMODIPINE [MART.]
Common Name English
NSC-758476
Code English
NIMOTOP
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-(2-METHOXYETHYL) 5-(1-METHYLETHYL) ESTER
Systematic Name English
NIMODIPINE [USP IMPURITY]
Common Name English
NIMODIPINE AP
Brand Name English
NIMODIPINE [ORANGE BOOK]
Common Name English
nimodipine [INN]
Common Name English
NIMODIPINE [JAN]
Common Name English
NEMOTAN
Brand Name English
Nimodipine [WHO-DD]
Common Name English
BAY-E-9736
Code English
NIMODIPINE [USP-RS]
Common Name English
BAY E 9736
Code English
NYMALIZE
Brand Name English
NIMODIPINE [USP MONOGRAPH]
Common Name English
NIMODIPINE [USAN]
Common Name English
(±)-NIMODIPINE
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/15/1554
Created by admin on Mon Mar 31 19:00:59 GMT 2025 , Edited by admin on Mon Mar 31 19:00:59 GMT 2025
LIVERTOX NBK548041
Created by admin on Mon Mar 31 19:00:59 GMT 2025 , Edited by admin on Mon Mar 31 19:00:59 GMT 2025
NDF-RT N0000175421
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NCI_THESAURUS C333
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NDF-RT N0000000069
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WHO-ATC C08CA06
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FDA ORPHAN DRUG 343711
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NDF-RT N0000007556
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FDA ORPHAN DRUG 566016
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FDA ORPHAN DRUG 338611
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WHO-VATC QC08CA06
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Code System Code Type Description
DRUG BANK
DB00393
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PRIMARY
DAILYMED
57WA9QZ5WH
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PRIMARY
CAS
66085-59-4
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PRIMARY
MERCK INDEX
m7906
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PRIMARY Merck Index
PUBCHEM
4497
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PRIMARY
RS_ITEM_NUM
1463858
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PRIMARY
ChEMBL
CHEMBL1428
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PRIMARY
ECHA (EC/EINECS)
266-127-0
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PRIMARY
SMS_ID
100000092273
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PRIMARY
LACTMED
Nimodipine
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PRIMARY
CHEBI
7575
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PRIMARY
IUPHAR
2523
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PRIMARY
EPA CompTox
DTXSID5023370
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PRIMARY
RXCUI
7426
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PRIMARY RxNorm
FDA UNII
57WA9QZ5WH
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PRIMARY
INN
4528
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PRIMARY
EVMPD
SUB09297MIG
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PRIMARY
NSC
758476
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PRIMARY
WIKIPEDIA
NIMODIPINE
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PRIMARY
DRUG CENTRAL
1937
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PRIMARY
NCI_THESAURUS
C692
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PRIMARY
MESH
D009553
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PRIMARY
ACTIVE MOIETY
Structure of Nimodipine
METABOLITE (PARENT)
Structure of Dehydro Nimodipine
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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