Grundinformationen
- Standard-SMILES
COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(C(c3ccccc3)c3ccccc3)CC2)C1c1cccc([N+](=O)[O-])c1- InChIKey
ANEBWFXPVPTEET-UHFFFAOYSA-N- Summenformel
- C35H38N4O6
- Durchschnittliche Molmasse
- 610,7 g/mol
- Monoisotopische Masse
- 610,27913494
Namen und Bezeichner
- Bevorzugter Name
- Manidipine
- IUPAC
- 5-O-[2-(4-benzhydrylpiperazin-1-yl)ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- Englischer Name
- Manidipine
- Summenformel
- C35H38N4O6
- Molmasse
- 610.7
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
89226-50-6- PubChem CID
- 4008
- DTXSID
DTXSID2043745- ChEMBL
CHEMBL1085699、CHEMBL312176- ChEBI
CHEBI:135849- UNII
- 6O4754US88
- EC Number
- 855-394-4
- Nikkaji
- J313.870D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,6
- Polarare Oberfläche (TPSA)
- 117 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 45
- Formalladung
- 0
- Komplexität
- 1.090
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 125 · 125-128°C
- Siedepunkt
- 722 · 722.0±60.0 °C(Predicted)
- Dichte
- 1.232 · 1.232±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 10 mM · Soluble in DMSO > 10 mM
- Aggregatzustand
- Powder
- pka
- 6.12 · 6.12±0.10(Predicted)
- Farbe
- Light yellow to yellow
- LogP
- 4.135 · 4.135
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.;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)
Manidipine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Regulatorische Informationen
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
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;C08CA11 - Manidipine
QC - Cardiovascular system;QC08 - Calcium channel blockers;QC08C - Selective calcium channel blockers with mainly vascular effects;QC08CA - Dihydropyridine derivatives;QC08CA11 - Manidipine
Mechanism of Action
Contraction of vascular smooth muscle is stimulated by Gq coupled receptors which produce calcium release from the sarcoplasmic reticulum. This is followed by opening of voltage dependent calcium channels and an influx of calcium into the cell ultimately producing contraction. Manidipine binds to and dissociates slowly from L- and T-type voltage dependent calcium channels on smooth muscle cells, blocking the entrance of extracellular calcium into the cell and preventing this contraction. This produces vasodilation which decreases blood pressure. Manidipine produces renal vasodilation and an increase in natriuresis. This likely contributes to the antihypertensive effect by reducing blood volume. Manidipine is selective for the vasculature and does not produce significant effects on the heart or central nervous system at clinically relevant dosages.
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.
Absorption, Distribution and Excretion
The median Tmax is 1.5 h. Administration with food produces an 1.3-1.6-fold increase in Cmax but no change in Tmax. Manidipine does not accumulate significantly with multiple doses.
Manidipine is eliminated through extensive metabolism. 63% is eliminated in the feces and 31% in the urine as metabolites.
Verwendung und Herstellung
Anwendungen
BeschreibungManidipine is a dihydropyridine L- and T-type calcium channel blocker. It blocks recombinant rabbit L-type (α1Cα2/δβ1a) and human T-type (α1H) calcium channels expressed in Xenopus oocytes and native L-type channels in dissociated guinea pig cardiac ventricular cells (IC50 = 2.6 nM). Manidipine inhibits intracellular calcium increases induced by endothelin-1 (ET-1; ) in A7r5 rat vascular smooth muscle cells (ED50 = 1 nM) and potassium-induced contraction of isolated dog femoral and portal veins (IC50s = 24 and 2.1 nM, respectively). In vivo, it lowers blood pressure in spontaneously hypertensive rats (SHRs) when administered at a dose of 10 mg/kg and inhibits left ventricular hypertrophy in rats induced by isoproterenol when administered at a dose of 3 mg/kg. Formulations containing manidipine have been used in the treatment of hypertension.
VerwendenManidipine (Manyper) is a lipophilic, third-generation, highly vasoselective dihydropyridine calcium antagonist with an IC50 of 2.6 nM. It causes systemic vasodilation by inhibiting the voltage-dependent calcium inward currents in smooth muscle cells. It
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