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ニモジピン
ニモジピン · 1,4-ジヒドロ-4-(3-ニトロフェニル)-2,6-ジメチルピリジン-3,5-ジカルボン酸3-イソプロピル5-(2-メトキシエチル) · 2,6-ジメチル-4-(3-ニトロフェニル)-1,4-ジヒドロピリジン-3,5-ジカルボン酸3-イソプロピル5-(2-メトキシエチル) · 1,4-ジヒドロ-2,6-ジメチル-4-(3-ニトロフェニル)-3,5-ピリジンジカルボン酸3-イソプロピル5-(2-メトキシエチル) · 1,4-ジヒドロ-2,6-ジメチル-4-(3-ニトロフェニル)ピリジン-3,5-ジカルボン酸3-イソプロピル5-(2-メトキシエチル) · 1,4-ジヒドロ-2,6-ジメチル-4-(3-ニトロフェニル)-3,5-ピリジンジカルボン酸イソプロピル2-メトキシエチル · 3-(2-メトキシエチル) 5-プロパン-2-イル 2,6-ジメチル-4-(3-ニトロフェニル)-1,4-ジヒドロピリジン-3,5-ジカルボキシラート · NIMOTOP
識別子と物理属性
| CAS No. | 66085-59-4 |
|---|---|
| 分子式 | C21H26N2O7 |
| 平均分子量 | 418.4 g/mol |
| 単同位体質量 | 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 |
| 現地名 | ニモジピン |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 120 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 8 |
| 回転可能結合数 | 9 |
| 重原子数 | 30 |
| 形式電荷 | 0 |
| 複雑度 | 736 |
| LogP（分配係数） | 3.052.7 |
| 溶解度 | 1.20e-02 g/Lメタノール: 62.5 mg/mL |
| 融点 | 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)] |
| 沸点 | 536.21°C (rough estimate) |
| 密度 | 1.3268 (rough estimate) |
| 屈折率 | 1.6500 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 2.77±0.70(Predicted) |
| 色 | 白い |
| Merck | 14,6551 |
| 安定性 | 購入日から2年間安定です。この DMSO 溶液は、-20°C で 3 か月間保存できます。 |
| 主な用途 | 医薬品（低分子化合物） |
| 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 データベース | 66085-59-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Nimodipine(66085-59-4) |
化学的特性
Crystalline Solid
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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%) |
| 有害作用 | 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. |
| 毒性の概要 | 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 |
| 水環境危害等級（WGK） | 1 |
| RTECS 番号 | US7975500 |
| 毒性 | LD50 in mice, rats (mg/kg): 3562, 6599 orally33, 16 i.v. (Schlüter) |
| 税関コード | 29333990 |
| 危険文句（R） | 20/21/22-48/22 |
| 危険表示 | Xn |
| 安全措置（S） | 36 |
| 危険等級 | IRRITANTAcute Tox. 4 Oral |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
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.
使用
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
一般的な説明
Nimodipine, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)- 3,5-pyridinedicarboxylic acid 2-methoxyethyl1-methylethyl ester (Nimotop), is another dihydropyridinecalcium channel blocker but differs in that it dilatesthe cerebral blood vessels more effectively than do the otherdihydropyridine derivatives. This drug is indicated for treatmentof subarachnoid hemorrhage-associated neurologicaldeficits.