Nimodipine

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 Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663415
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 95 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2565839	Antagonist 2849		0.27 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Subarachnoid hemorrhage 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018869s014lbl.pdf	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
Subarachnoid hemorrhage 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203340lbl.pdf	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
Subarachnoid hemorrhage 8 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a0a13a26-b9dc-4ed1-b2c4-46e14fb60bfc	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-005-8384-4	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7620235/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22001996/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2290231/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Nephroprotective effect of calcium channel blockers against toxicity of lead exposure in mice.	2013-04-26	23428833
Role of voltage gated Ca2+ channels in rat visceral hypersensitivity change induced by 2,4,6-trinitrobenzene sulfonic acid.	2013-03-28	23537331
Biochemical, histopathological and clinical evaluation of delayed effects caused by methamidophos isoforms and TOCP in hens: ameliorative effects using control of calcium homeostasis.	2012-12-08	22974967
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.	2012-10	22700542
Identification and validation of novel human pregnane X receptor activators among prescribed drugs via ligand-based virtual screening.	2011-02	21068194
Organophosphorus-induced delayed neuropathy: a simple and efficient therapeutic strategy.	2010-02-01	19914363
Intraarterial nimodipine infusion to treat symptomatic cerebral vasospasm after aneurysmal subarachnoid hemorrhage.	2009-09	19844625
Cell death induced by zinc and cadmium is mediated by clusterin in cultured mouse seminiferous tubules.	2009-07	19288494
Chloride channels as drug targets.	2009-02	19153558
Nimodipine and its use in cerebrovascular disease: evidence from recent preclinical and controlled clinical studies.	2008-11	19021025
Protective effect of L-type calcium channel blockers against haloperidol-induced orofacial dyskinesia: a behavioural, biochemical and neurochemical study.	2008-09	18363098
Ammonia inhibits the C-type natriuretic peptide-dependent cyclic GMP synthesis and calcium accumulation in a rat brain endothelial cell line.	2008-05	18222015
A number of marketed dihydropyridine calcium channel blockers have mineralocorticoid receptor antagonist activity.	2008-03	18250364
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.	2008-02-06	18178321
L-type calcium channel blockade on haloperidol-induced c-Fos expression in the striatum.	2007-11-09	17913375
Amphetamine-induced anxiety-related behavior in animal models.	2007-06-28	18195452
[Effect of nimodipine on mechanisms of HL-60 cell apoptosis induced by cytarabine].	2007-02	17490525
Protective effect of adenosine reuptake inhibitors in haloperidol-induced orofacial dyskinesia and associated behavioural, biochemical and neurochemical changes.	2007	17377417
Dose-finding study with nimodipine: a selective central nervous system calcium channel blocker on aminophylline induced seizure models in rats.	1998-03-15	9570719
Haemodynamic effects of intravenous nimodipine following aneurysmal subarachnoid haemorrhage: implications for monitoring.	1997-05	9165970
Effect of calcium channel blockers on withdrawal syndrome of lorazepam in rats.	1996-06	8707372
Preliminary study on controlled hypotension induced by nimodipine in craniocerebral surgery.	1995-06	7555250
Hypotensive effect of nimodipine during treatment for aneurysmal subarachnoid haemorrhage.	1995	8748871
Cocaine toxicity and the calcium channel blockers nifedipine and nimodipine in rats.	1994-01-01	8163794
Sinus arrest after nimodipine treatment for a head injury.	1994	8061545
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.	1993-07	8369013
Quinine-induced tinnitus in rats.	1991-10	1910705
Nimodipine pretreatment improves cerebral blood flow and reduces brain edema in conscious rats subjected to focal cerebral ischemia.	1990-11	2211883
Protective effect of nimodipine against ischemic neuronal damage in rat hippocampus without changing postischemic cerebral blood flow.	1990-09	2384539
HIV-1 coat protein neurotoxicity prevented by calcium channel antagonists.	1990-04-20	2326646
Effect of treatment with nimodipine in patients with mild and moderate essential hypertension.	1990-04	2338687
Oxytocin-induced penile erection and yawning: role of calcium and prostaglandins.	1990-03	2339153
Calcium channel inhibitors prevent apomorphine- and oxytocin-induced penile erection and yawning in male rats.	1989-08-03	2806374
Effect of oral nimodipine on cerebral infarction and outcome after subarachnoid haemorrhage: British aneurysm nimodipine trial.	1989-03-11	2496789
Effects of nimodipine on the production of thromboxane A2 following total global cerebral ischemia.	1988-09	3404240
Therapeutic trial of intravenous nimodipine in patients with established cerebral vasospasm after rupture of intracranial aneurysms.	1988-08	3054619
Nimodipine treatment of subarachnoid hemorrhage.	1988	3233859
Differential effects of 1,4-dihydropyridine calcium channel blockers: therapeutic implications.	1987-11	3323259
Ca2+ modulators as antidotes to imipramine and neurotransmitter toxicity.	1987-09	2886994
Nimodipine-treated subarachnoid hemorrhage associated with acute pseudo-obstruction of the colon.	1987-08	3603356
Non-vascular action of calcium blockers in migraine: pupillopharmacological study.	1986-10-01	3038706
[Nimodipine, nifedipine and vincamine improve amnesia induced by anisodine and sodium nitrite in rats and mice].	1986-10	2952309
[Ergotism with cerebral complications. Case report and review of the literature].	1986-04-05	3961460
Magnetic resonance imaging in the evaluation of nimodipine-treated acute experimental focal cerebral ischemia.	1986	2980536
Blood pressure and heart rate during treatment with nimodipine in patients with subarachnoid hemorrhage.	1985-05	4010871
Implications of nimodipine prophylaxis of cerebral vasospasm on anesthetic management during intracranial aneurysm clipping.	1985-02	3881564
Cerebral blood flow and neurologic outcome when nimodipine is given after complete cerebral ischemia in the dog.	1984-03	6693515
Cerebral arterial spasm--a controlled trial of nimodipine in patients with subarachnoid hemorrhage.	1983-03-17	6338383
Effect of nimodipine (Bay e 9736) on postischaemic cerebrovascular reactivity, as revealed by measuring regional cerebral blood flow (rCBF).	1982	7102420

Patents

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 Created by `admin` on `Mon Mar 31 19:00:59 GMT 2025` Edited by `admin` on `Mon Mar 31 19:00:59 GMT 2025`
Record UNII	57WA9QZ5WH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Nimodipine

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