Nitrendipine

HCID 4507

Basic information

CAS
39562-70-4
Standard SMILES
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1
InChIKey
PVHUJELLJLJGLN-UHFFFAOYSA-N
Molecular formula
C18H20N2O6
Average molar mass
360.4 g/mol
Monoisotopic mass
360.13213636

Names & identifiers

Preferred name
Nitrendipine
IUPAC
5-O-ethyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
English name
Nitrendipine
Molecular formula
C18H20N2O6
Molecular weight
360.36

Names & synonyms

nitrendipine39562-70-4BayotensinBaypressNidrelDeiten3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateNitrendipinumBay-e-5009NitrendipinoNitrepinBAY e 5009
Show more names
Nitrendipinbaye5009Bylotensin
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid ethyl methyl esterDTXSID00233739B627AW319NSC-758466CHEBI:7582DTXCID2033733,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, ethyl methyl esternitrendipincorax

Database identifiers

CAS
39562-70-4
PubChem CID
4507
DTXSID
DTXSID0023373
ChEMBL
CHEMBL3195219、CHEMBL475534
ChEBI
CHEBI:7582
UNII
9B627AW319
EC Number
254-513-1
Nikkaji
J16.451H

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
110 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
6
Heavy atoms
26

Experimental & physicochemical properties

LogP · 2 items

2.88

2.4

Solubility · 2 items

Insoluble

1.42e-02 g/L

Melting Point · 2 items

156-160 °C

156 - 160 °C

Caco2 Permeability-4.77
Physical DescriptionSolid
Kovats Retention Index2659.11

Physicochemical properties

Melting point
1580 C · 1580C
Boiling point
492.4 °C · 492.4°C (rough estimate)
Density
1.3595 · 1.3595 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
storage temp.
2 · 2-8°C
solubility
15 mg/mL · methanol: 15 mg/mL

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.1% (1 of 95) of reports.

Warning

H302+H312 (29.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal];H302 (29.5%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (73.7%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (44.2%): Harmful if inhaled [Warning Acute toxicity, inhalation];H361 (25.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 95 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 95 reports by companies.;There are 4 notifications provided by 94 of 95 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (29.5%);Acute Tox. 4 (73.7%);Acute Tox. 4 (44.2%);Repr. 2 (25.3%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Nitrendipine

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation · 1 item

◉ Summary of Use during Lactation;Based on limited data, it is unlikely that nitrendipine will reach the infant in clinically important amounts. However, it may be preferable to use another agent drug for which more safety information is available.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
rtecs
US5653000
Toxicity
LD50 in mice, rats (mg/kg): 39, 12.6 i.v.; 2540, >10000 orally (Hoffmann)
risk_code
20/21/22
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system;C08 - Calcium channel blockers;C08C - Selective calcium channel blockers with mainly vascular effects;C08CA - Dihydropyridine derivatives;C08CA08 - Nitrendipine

QC - Cardiovascular system;QC08 - Calcium channel blockers;QC08C - Selective calcium channel blockers with mainly vascular effects;QC08CA - Dihydropyridine derivatives;QC08CA08 - Nitrendipine

Protein Binding> 99%
Pharmacodynamics · 1 item

Nitrendipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nitrendipine is similar to other peripheral vasodilators. Nitrendipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

Mechanism of Action · 1 item

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Nitrendipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

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.

Cellular LocationsMembrane

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >2500;Consumption (g per capita; approx.) in Germany (2009): 0.0305;Excretion rate: 1;Calculated removal (%): 28.5
Applications · 5 items

DescriptionNitrendipine is a vasodilating, dihydropyridine calcium antagonist. Its prolonged therapeutic effect in comparison to nifedipine makes it useful in the once to twice daily treatment of hypertension.

UsesNitrendipine modulates NMDA receptor channel function in mammalian neurons. Nitrendipine has been shown to inhibit neutrophil adhesion to vascular endothelium. It is used in the treatment of primary hypertension to decrease blood pressure. Nitrendipine is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina.

UsesAntihypertensive;Calcium channel blocker

UsesNitrendipine is a dihydropyridine calcium channel blocker. Nitrendipine is used in the treatment of primary (essential) hypertension to decrease blood pressure. Antihypertensive.

General DescriptionNitrendipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ethylester (Baypress), is a second-generation dihydropyridinechannel blocker of the nifedipine type. It is more selectivefor vascular smooth muscle than for myocardial tissue andserves as an effective vasodilator. The drug is used in thetreatment of mild-to-moderate essential hypertension.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in t e treatment of hypertension.

Related reactions

1 records

Compound notes

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