Bupivacaine (USAN:INN:BAN)
BUPIVACAINE BASE · MARCAINE · Anekain · Levobupivacaine (Bupivacaine) · 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide · 1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide · LAC-43 · win11318
식별자 및 물리적 특성
| CAS No. | 2180-92-9 |
|---|---|
| 분자식 | C18H28N2O |
| 평균 분자량 | 288.4 g/mol |
| 단동위원소 질량 | 288.22016352 g/mol |
| SMILES | CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C |
| InChIKey | LEBVLXFERQHONN-UHFFFAOYSA-N |
| PubChem CID | 2474 |
| ChEBI | CHEBI:77431 |
| DTXSID | DTXSID2022703 |
화학 및 물리적 성질
| XLogP | 3.4 |
|---|---|
| 극성 표면적 | 32.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 21 |
| 형식 전하 | 0 |
| 복잡도 | 321 |
| 의약품 | Pharmaceuticals |
| LogP(분배 계수) | 3.6 |
| 용해도 | 9.77e-02 g/L |
| Human Drugs | Pharmaceuticals |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| 녹는점 | 107 - 108 °C107.5-108° |
| Physical Description | Solid |
| Collision Cross Section | 173.1 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]180.07 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 끓는 점 | 430.65°C (rough estimate) |
| 밀도 | 1.0238 (rough estimate) |
| 굴절률 | 1.5700 (estimate) |
| pKa(산도 계수) | 8.09also reported as 8.17(at 25℃) |
| 용해도 | 101.5mg/L(25℃) |
| InChI | InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21) |
| InChIKey | LEBVLXFERQHONN-UHFFFAOYSA-N |
| SMILES | C1(CCCCN1CCCC)C(=O)NC1C(C)=CC=CC=1C |
| NIST | 2-Piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-(2180-92-9) |
| EPA | 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)- (2180-92-9) |
안전 및 규제
| 운송 번호(UN) | 2811 |
|---|---|
| 위험 문구(R) | 26/27/28-38-41 |
| 위험 표시 | T+ |
| 안전 문구(S) | 22-26-36/37/39-45 |
용도
용도
Like lidocaine and mepivacaine, bupivacaine is used in infiltration, spinal, and epidural anesthesia in blocking nerve transmission. Its most distinctive property is its long-lasting action. It is used for surgical intervention in urology and in lower thoracic surgery from 3 to 5 h in length, and in abdominal surgery lasting from 45 to 60 min. It is used to block the trifacial nerve, the sacral and brachial plexuses, in resetting dislocations, in epidural anesthesia, and during Cesarian sections.
일반 설명
Bupivacaine was synthesized simultaneously with mepivacainein 1957 but was at first overlooked because of the increasedtoxicity compared with mepivacaine. When themethyl on the cyclic amine of mepivacaine is exchanged fora butyl group the lipophilicity, potency and the duration ofaction all increase. Literature reports of cardiovascular toxicity,including severe hypotension and bradycardia, areabundant in the literature.91 Bupivacaine is highly bound toplasma proteins (95%), and thus the free concentration mayremain low until all of the protein binding sites are occupied.After that point, the plasma levels of bupivacaine rise rapidlyand patients may progress to overt cardiac toxicity withoutever showing signs of CNS toxicity. The cardiotoxicity ofbupivacaine is a result of its affinity to cardiac tissues and itsability to depress electrical conduction and predispose theheart to reentry types of arrhythmias. The cardiotoxicity ofbupivacaine was found to be significantly more prominentwith the “R” isomer, or the racemic mixture, thus the “S”stereoisomer is now on the market as levobupivacaine.