Nitrendipin
Nitrendipine
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Grundinformationen
- 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- Summenformel
- C18H20N2O6
- Durchschnittliche Molmasse
- 360,4 g/mol
- Monoisotopische Masse
- 360,13213636
Überblick
Nitrendipine is 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 the treatment of hypertension. It has a role as a geroprotector, a vasodilator agent, an antihypertensive agent and a calcium channel blocker. It is a member of dicarboxylic acids and O-substituted derivatives, an ethyl ester, a methyl ester, a C-nitro compound, a dihydropyridine and a diester.
Namen und Bezeichner
- Bevorzugter Name
- Nitrendipine
- IUPAC
- 5-O-ethyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- Lokaler Name
- Nitrendipin
- Englischer Name
- Nitrendipine
- Summenformel
- C18H20N2O6
- Molmasse
- 360.36
Namen und Synonyme
nitrendipine39562-70-4BayotensinBaypressNidrelDeitenNitrendipinoNitrendipinumNitrepin3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateBay-e-5009BAY e 5009
Weitere Namen anzeigen
Nitrendipinbaye5009Bylotensin
nitrendipincoraxNitrePuren1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid ethyl methyl esterDTXSID00233739B627AW319NSC-758466CHEBI:7582DTXCID203373
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,9
- Polarare Oberfläche (TPSA)
- 110 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 661
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
LogP
2.4
2.88
Solubility
Insoluble
1.42e-02 g/L
Human DrugsBreast Feeding; Lactation; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents
Melting Point
156-160 °C
156 - 160 °C
Physical DescriptionSolid
Collision Cross Section
181.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
182.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
189.51 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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]
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (29.5%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Nitrendipine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- wgk
- 1
- RTECS-Nr.
- US5653000
- risk_code
- 20/21/22
- Toxizität
- LD50 in mice, rats (mg/kg): 39, 12.6 i.v.; 2540, >10000 orally (Hoffmann)
- hazard_code
- Xn
- safety_code
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding> 99%
Pharmacodynamics
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
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
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.
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