Manidipine

HCID 4008CAS 89226-50-6

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

manidipine89226-50-6FranidipineArtedilManidipine 6300Manidipino5-O-[2-(4-benzhydrylpiperazin-1-yl)ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate6O4754US88DTXSID20437452-(4-Diphenylmethyl-1-piperazinyl)ethyl methyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate3-{2-[4-(diphenylmethyl)piperazin-1-yl]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylatemanidipinum
Weitere Namen anzeigen
Manidipine (Manyper)IpertenManidipine(base)Manidipine(CV-4093)Manidipine Impurity1254Manidipine (10mM in DMSO)
3-(2-(4-(diphenylmethyl)piperazin-1-yl)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate5-O-(2-(4-benzhydrylpiperazin-1-yl)ethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylatemanidipine, (+-)-RefChem:809939DTXCID0023745C08CA11120092-68-43-(2-(4-Benzhydrylpiperazin-1-yl)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

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

Experimentelle und physikochemische Eigenschaften

Solubility<1mg/mL

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Regulatory InformationStatus: Active Update: 11-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33372
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Manidipine

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Regulatorische Informationen

Regulatory InformationStatus: Active Update: 11-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33372

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

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

Protein BindingManidipine is 99% bound to human plasma proteins.
PharmacodynamicsManidipine produces vasodilation resulting in lower blood pressure.
Mechanism of Action · 1 Eintrag

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.

Biological Half-LifeThe half life of elimination has been observed to be dose dependent. Doses of 5, 10, and 20 mg produced half lives of 3.94, 5.02, and 7.95 h respectively.
Metabolism/MetabolitesManidipine is extensively metabolized by CYP enzymes to pyridine derivatives and diphenylmethane derivatives which make up 4-7% and 22-24% of the dose excreted in the urine.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >25;Consumption (g per capita; approx.) in Germany (2009): 0.000305;Calculated removal (%): 83.1
Anwendungen · 2 Einträge

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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上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

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