Grundinformationen
- 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
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
Weitere Namen anzeigen
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 Struktureigenschaften
- 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
LogP
2.88
2.4
Solubility
Insoluble
1.42e-02 g/L
Melting Point
156-160 °C
156 - 160 °C
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)]
191.32 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];180.38 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];189.51 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 1580 C · 1580C
- Siedepunkt
- 492.4 °C · 492.4°C (rough estimate)
- Dichte
- 1.3595 · 1.3595 (rough estimate)
- Brechungsindex
- 1.57 · 1.5700 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 15 mg/mL · methanol: 15 mg/mL
- Aggregatzustand
- powder
- pka
- 2.79 · 2.79±0.70(Predicted)
- Farbe
- yellow to green
- Wasserlöslichkeit
- Soluble in DMSO (17.5 mg/ml), methanol (15 mg/ml), ethyl acetate, and ethanol (25 mM). Insoluble in water.
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Protect from light. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 week.
- InChI
- InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3
- InChIKey
- PVHUJELLJLJGLN-UHFFFAOYSA-N
- SMILES
- C1(C)NC(C)=C(C(OC)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OCC)=O
- CAS Datenbank
- 39562 · 39562-70-4(CAS DataBase Reference)
- NIST chemische Informationen
- Nitrendipine(39562-70-4)
Sicherheit und Regulatorisches
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];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.
Gefahrenhinweise
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;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.
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
- 36
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
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
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.
Drugs used to cause dilation of the blood vessels.
Verwendung und Herstellung
Anwendungen
BeschreibungNitrendipine 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.
VerwendenNitrendipine is a dihydropyridine calcium channel blocker. Nitrendipine is used in the treatment of primary (essential) hypertension to decrease blood pressure. Antihypertensive.
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Ergänzende Hinweise
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.
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