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Nimodipin
NIMOTOP · Nimodipin · 2-methyo-xyethyl 1-methylethyl ester · 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-isopropyl 5-(2-methoxyethyl) ester · Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester · ADMON · PERIPLUM · Nimodipime
Identifikatoren & physikalische Daten
| CAS No. | 66085-59-4 |
|---|---|
| Summenformel | C21H26N2O7 |
| Durchschnittliche Molmasse | 418,4 g/mol |
| Monoisotopische Masse | 418,17400117 g/mol |
| SMILES | COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1 |
| InChIKey | UIAGMCDKSXEBJQ-UHFFFAOYSA-N |
| PubChem CID | 4497 |
| ChEMBL | CHEMBL1428 |
| ChEBI | CHEBI:7575 |
| EC No. | 266-127-0 |
| DTXSID | DTXSID5023370 |
| Lokaler Name | Nimodipin |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 120 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 30 |
| Formalladung | 0 |
| Komplexität | 736 |
| LogP (Verteilungskoeffizient) | 3.052.7 |
| Löslichkeit | 1.20e-02 g/Lmethanol: 62.5 mg/mL |
| Schmelzpunkt | 125125 °C125°C |
| Physical Description | Solid |
| Kovats Retention Index | 2840.44 |
| Collision Cross Section | 202.11 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]182.83 Ų [M+H-H2O]+ [CCS Type: TW198.78 Ų [M+Na]+ [CCS Type: TW194.6 Ų [M+H]+ [CCS Type: TW197.8 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Siedepunkt | 536.21°C (rough estimate) |
| Dichte | 1.3268 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 2.77±0.70(Predicted) |
| Farbe | white |
| Merck | 14,6551 |
| Stabilität | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChI | InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3 |
| InChIKey | UIAGMCDKSXEBJQ-UHFFFAOYSA-N |
| SMILES | C1(C)NC(C)=C(C(OC(C)C)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OCCOC)=O |
| CAS Datenbank | 66085-59-4(CAS DataBase Reference) |
| NIST chemische Informationen | Nimodipine(66085-59-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.WarningH315 (35.8%): Causes skin irritation [Warning Skin corrosion/irritation]H361 (37.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]H373 (58.2%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]P203, P260, P264, P280, P302+P352, P318, P319, P321, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 67 reports by companies from 7 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 67 reports by companies.There are 6 notifications provided by 66 of 67 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. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the product |
| Hazard Classes and Categories | Skin Irrit. 2 (35.8%)Repr. 2 (37.3%)STOT RE 2 (58.2%) |
| Unerwünschte Wirkungen | Nimodipine is usually well-tolerated orally, but its use correlates with some side effects related to its use as a vasodilator. The most common adverse effects of this medication include headache, vertigo, flushing, nausea, diarrhea, pedal edema, rash, and palpitations.Acute colonic pseudo-obstruction (Ogilvie syndrome) has been documented in patients administered oral nimodipine. Internal carotid and middle cerebral artery narrowing leading to cerebral infarction have been reported 5 months after intraventricular administration of sustained-release nimodipine.Drug-Drug InteractionsNimodipine is metabolized by the cytochrome P450 3A4 system. Drugs that inhibit this enzyme can cause elevated plasma concentrations of nimodipine. These drugs include macrolide antibiotics (eg, erythromycin, clarithromycin, and telithromycin), protease inhibitors (eg, ritonavir, indinavir, nelfinavir, and saquinavir), "-azole" antimycotics (eg, ketoconazole, voriconazole, itraconazole), antidepressants (eg, nefazodone, fluoxetine), quinupristin/dalfopristin, cimetidine, and valproic acid. Grapefruit juice also inhibits this cytochrome system and should be avoided by any patient taking nimodipine.Medications including carbamazepine, phenobarbital (phenobarbitone), and phenytoin are CYP3A4 inducers. Concomitant administration of any of these medications enhances nimodipine's metabolism. This process reduces nimodipine's serum concentration and increases the likelihood of treatment failure. |
| Toxizitätsübersicht | Signs and Symptoms of OverdoseAcute toxicity due to overdose can cause significant hypotension, cardiac arrhythmia, nausea, and vomiting. Refractory, nimodipine-induced vasoplegia may occur.Management of OverdoseNo specific antidote is available. Overdoses are managed initially by discontinuing nimodipine and treating symptoms. Gastric lavage may be considered if the toxicity is due to oral intake, and charcoal can be administered in emergencies. Hypotension is managed with inotropes, and arrhythmias are managed by cardiologists and emergency department staff. Since nimodipine is highly protein-bound, dialysis is unlikely to be beneficial.Recent case reports suggest hydroxocobalamin as a potential rescue therapy for nimodipine-induced refractory vasoplegia. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)NimodipineAmbiguous-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during LactationBased on limited data, amounts ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants.◉ Effects in Breastfed InfantsRelevant published information was not found as of the revision date.◉ Effects on Lactation and Breastmilk |
| Wassergefährdungsklasse (WGK) | 1 |
| Zollcode | 29333990 |
| RTECS-Nr. | US7975500 |
| R-Sätze (R) | 20/21/22-48/22 |
| Toxizität | LD50 in mice, rats (mg/kg): 3562, 6599 orally33, 16 i.v. (Schlüter) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 Oral |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Nimodipine is a cerebral vasodilating calcium antagonist related to nifedipine. It is indicated for the prophylaxis and treatment of neurological deficits due to cerebral vasospasm after subarachnoid hemorrhage.
Verwenden
Nimodipine has been used:as a L-type calcium channel (LTCC) inhibitor, to evaluate its neuroprotective activity in the vibrosectionsas a standard, in the enantioseparation of chiral drugs by high performance liquid chromatography (HPLC)in the pharmacological studies for the measurement of spine voltage escape