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Nimodipine

HCID 4497
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Basic information

CAS
66085-59-4
Standard SMILES
COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1
InChIKey
UIAGMCDKSXEBJQ-UHFFFAOYSA-N
Molecular formula
C21H26N2O7
Average molar mass
418.4 g/mol
Monoisotopic mass
418.17400117

Overview

Nimodipine can cause developmental toxicity according to state or federal government labeling requirements.

Names & identifiers

Preferred name
Nimodipine
IUPAC
3-O-(2-methoxyethyl) 5-O-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
English name
Nimodipine
Molecular formula
C21H26N2O7
Molecular weight
418.44

Names & synonyms

nimodipine66085-59-4NimotopPeriplumAdmonNimodipinoNymalizeNimodipinumBAY e 9736nemotanBay-e-9736Nimodipine ap
Show more names
Nimodipin2-methyo-xyethyl 1-methylethyl ester1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-isopropyl 5-(2-methoxyethyl) esterIsopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl esterNimodipime
Nimodipin ISISDTXSID5023370Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 1-methylethyl ester57WA9QZ5WHNSC-758476CHEBI:75753-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Database identifiers

Properties

Computed structural propertiesFilling in

XLogP
3.1
Topological polar surface area
120 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
9
Heavy atoms
30
Formal charge
0
Complexity
736

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

2.7

2.82

Solubility1.20e-02 g/L
Human Drugs · 4 items

Breast Feeding; Lactation; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point125 °C
Physical DescriptionSolid
Collision Cross Section · 2 items

198.78 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

197.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.

Warning

H315 (35.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P260, P264, P280, P302+P352, P318, P319, P321, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationHazard Traits - Developmental Toxicity
Hazard Classes and CategoriesSkin Irrit. 2 (35.8%)

Toxicology

Adverse Effects · 1 item

Nimodipine is usually well-tolerated orally, but its use correlates with some side effects related to its use as a vasodilator. The most common adverse effects of this medication include headache, vertigo, flushing, nausea, diarrhea, pedal edema, rash, and palpitations.

Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nimodipine

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

ATC Code · 3 items

C08CA06

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding95% bound to plasma protein
Pharmacodynamics · 1 item

Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. 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 congenital aneurysms who are in good neurological condition post-ictus (e.g., Hunt and Hess Grades I-III). The contractile processes of smooth muscle cells are dependent upon calcium ions, which enter these cells during depolarization as slow ionic transmembrane currents. Nimodipine inhibits calcium ion transfer into these cells and thus inhibits contractions of vascular smooth muscle. In animal experiments, nimodipine had a greater effect on cerebral arteries than on arteries elsewhere in the body perhaps because it is highly lipophilic, allowing it to cross the blood brain barrier.

Mechanism of Action · 1 item

Although the precise mechanism of action is not known, nimodipine blocks intracellular influx of calcium through voltage-dependent and receptor-operated slow calcium channels across the membranes of myocardial, vascular smooth muscle, and neuronal cells. By specifically binding to L-type voltage-gated calcium channels, nimodipine inhibits the calcium ion transfer, resulting in the inhibition of vascular smooth muscle contraction. Evidence suggests that the dilation of small cerebral resistance vessels, with a resultant increase in collateral circulation, and/or a direct effect involving the prevention of calcium overload in neurons may be responsible for nimodipine's clinical effect in patients with subarachnoid hemorrhage.

Biological Half-Life1.7-9 hours
Metabolism/Metabolites · 2 items

Hepatic metabolism via CYP 3A4.

Nimodipine has known human metabolites that include 2,6-Dimethyl-4-(3-nitrophenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid, Dehydro nimodipine, and Unii-96S4GG1upr.

Related reactions

3 records
New reaction record
HRID 615181 reaction equation
HRID 615181As reactantuspto-grants-1985_02
HRID 845572 reaction equation
HRID 845572As productuspto-grants-1988_07
HRID 1387604 reaction equation
HRID 1387604As reactantuspto-grants-2001_07

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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CAS
66085-59-4
PubChem CID
4497
DTXSID
DTXSID5023370
ChEMBL
CHEMBL1428、CHEMBL3197349
ChEBI
CHEBI:7575
UNII
57WA9QZ5WH
EC Number
266-127-0
Nikkaji
J19.052G
Melting point
125 °C · 125°C
Boiling point
536.21 °C · 536.21°C (rough estimate)
Density
1.3268 · 1.3268 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
2 · 2-8°C
solubility
62.5 mg/mL · methanol: 62.5 mg/mL
form
solid
pka
2.77 · 2.77±0.70(Predicted)
color
white
Merck
14 · 14,6551
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Major Application
pharmaceutical (small molecule)
InChI
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
InChIKey
UIAGMCDKSXEBJQ-UHFFFAOYSA-N
SMILES
C1(C)NC(C)=C(C(OC(C)C)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OCCOC)=O
CAS DataBase Reference
66085 · 66085-59-4(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
nimodipine
FDA UNII
57 WA9QZ5WH · 57WA9QZ5WH
NCI Drug Dictionary
nimodipine
ATC code
8 CA06 · C08CA06
Proposition 65 List
Nimodipine
NIST Chemistry Reference
Nimodipine(66085-59-4)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Protein binding
98 % · 98%
Excreted unchanged in urine
1 % · <1%
Volume of distribution
0.9 · 0.9-1.6(L/kg)
Biological half-life
1.1 · 1.1-1.7 / 22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
Hazard Codes
Xn
Risk Statements
20 · 20/21/22-48/22
Safety Statements
36 · 36
WGK Germany
1 · 1
RTECS
7975500 · US7975500
HazardClass
IRRITANT
HS Code
29333990 · 29333990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Toxicity
50 in · LD50 in mice, rats (mg/kg): 3562, 6599 orally; 33, 16 i.v. (Schlüter)
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Nimodipine

8.4

35.5

The recommended oral dose is 60 mg (two 30 mg capsules) every 4 hours for 21 consecutive days.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 360 mg/day, Lowest Therapeutic Dose (LTD): 4.5 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.

3-Dec-21

Safety data

wgk
1
rtecs
US7975500
hs_code
29333990
Toxicity
LD50 in mice, rats (mg/kg): 3562, 6599 orally; 33, 16 i.v. (Schlüter)
risk_code
20/21/22-48/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
36
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501
FDA Pharmacological Classification · 6 items

57WA9QZ5WH

NIMODIPINE

Mechanisms of Action [MoA] - Calcium Channel Antagonists

Established Pharmacologic Class [EPC] - Dihydropyridine Calcium Channel Blocker

Chemical Structure [CS] - Dihydropyridines

Nimodipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nimodipine is as a Calcium Channel Antagonist.

MeSH Pharmacological Classification · 3 items

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs used to cause dilation of the blood vessels.

Absorption, Distribution and Excretion · 2 items

In humans, nimodipine is rapidly absorbed after oral administration, and peak concentrations are generally attained within one hour. Bioavailability is 100% following intravenous administration and 3-30% following oral administration due to extensive first-pass metabolism.

Nimodipine is eliminated almost exclusively in the form of metabolites and less than 1% is recovered in the urine as unchanged drug. Numerous metabolites, all of which are either inactive or considerably less active than the parent compound, have been identified.

Cellular LocationsCytoplasm
Metabolite PathwaysNimodipine Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals
Applications · 7 items

Uses1. Calcium channel blockers. Nimodipine has anti-ischemic and anti-vasoconstriction effect. It is the drug to improve cerebral vasodilator and brain function. It can be used for treating ischemic cerebrovascular disease, mild to moderate hypertension, migraine, cerebral vasospasm, sudden deafness and the like. 2. Calcium channel blockers. Nimodipine is mainly used for the treatment of ischemic cerebrovascular disease and migraine. 3. A new calcium antagonist. Nimodipine is used for the treatment of cerebrovascular disorders, such as cerebral vasospasm, interim and early ischemic cerebrovascular migraine, and sudden deafness.

DescriptionNimodipine is a cerebral vasodilating calcium antagonist related to nifedipine. It is indicated for the prophylaxis and treatment of neurological deficits due to cerebral vasospasm after subarachnoid hemorrhage.

Usesprovitamin, antixerophthalamic

UsesA dihydropyridine calcium channel blocker. It is used as a vasodilator (cerebral).

UsesNimodipine has been used:as a L-type calcium channel (LTCC) inhibitor, to evaluate its neuroprotective activity in the vibrosectionsas a standard, in the enantioseparation of chiral drugs by high performance liquid chromatography (HPLC)in the pharmacological studies for the measurement of spine voltage escape

UsesUsed as a cerebral vasodilator. A dihydropyridine calcium channel blocker

General DescriptionNimodipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)- 3,5-pyridinedicarboxylic acid 2-methoxyethyl1-methylethyl ester (Nimotop), is another dihydropyridinecalcium channel blocker but differs in that it dilatesthe cerebral blood vessels more effectively than do the otherdihydropyridine derivatives. This drug is indicated for treatmentof subarachnoid hemorrhage-associated neurologicaldeficits.

Upstream & downstream products

Upstream raw materials

Isopropyl acetoacetate(2-METHYL-1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTEREthanol2-Methoxyethanol3-NitrobenzaldehydeCrotonic acid2-Methoxyethyl acetoacetateAmmonium hydroxide

Downstream products

NIMODIPINE RELATED COMPOUND B (50 MG) (BIS(2-METHOXYETHYL) 2,6-DIMETHYL-4-(3-NITROPHE-NYL)-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE) (AS)
Additional notes · 1 item

DefinitionChEBI: A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.