Bupivacain

Bupivacaine (USAN:INN:BAN)

HCID 2474CAS 2180-92-9

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Grundinformationen

Standard-SMILES: CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
InChIKey: LEBVLXFERQHONN-UHFFFAOYSA-N
Summenformel: C18H28N2O
Durchschnittliche Molmasse: 288,4 g/mol
Monoisotopische Masse: 288,22016352

Überblick

1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide is a piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline. It is a piperidinecarboxamide, a tertiary amino compound and an aromatic amide. It is a conjugate base of a 1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium.

Namen und Bezeichner

Bevorzugter Name: Bupivacaine (USAN:INN:BAN)
IUPAC: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Lokaler Name: Bupivacain
Englischer Name: Bupivacaine
Summenformel: C18H28N2O
Molmasse: 288.43

Namen und Synonyme

Bupivacaine [USAN:INN:BAN]2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (+-)-Bupivacaine (USAN:INN:BAN)RefChem:1080208bupivacaine1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide2180-92-938396-39-3DL-BupivacaineBupivacainaAnekain(+-)-Bupivacaine

Weitere Namen anzeigen

BUPIVACAINE BASEMARCAINELevobupivacaine (Bupivacaine)1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamideLAC-43win11318WIN 11318Carbostesin

Bupivacainum1-Butyl-2',6'-pipecoloxylidideBupivacainum [INN-Latin]Bupivacaina [INN-Spanish]dl-1-Butyl-2',6'-pipecoloxylidideExparel(+/-)-BupivacaineAH 250

Datenbank-Bezeichner

CAS: 2180-92-9、38396-39-3
PubChem CID: 2474
DTXSID: DTXSID2022703
ChEBI: CHEBI:77431
UNII: Y8335394RO
Nikkaji: J7.351B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,4
Polarare Oberfläche (TPSA): 32,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 5
Schwere Atome: 21
Formalladung: 0
Komplexität: 321

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals

LogP3.6

Solubility9.77e-02 g/L

Human DrugsPharmaceuticals

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

Melting Point107 - 108 °C

Physikochemische Eigenschaften

Schmelzpunkt: 107.5 · 107.5-108°
Siedepunkt: 430.65 °C · 430.65°C (rough estimate)
Dichte: 1.0238 · 1.0238 (rough estimate)
Brechungsindex: 1.57 · 1.5700 (estimate)
pka: 8.09 · 8.09; also reported as 8.17(at 25℃)
Wasserlöslichkeit: 101.5 mg/L · 101.5mg/L(25 ºC)
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
CAS Datenbank: 2180 · 2180-92-9(CAS DataBase Reference)
NIST chemische Informationen: 2 · 2-Piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-(2180-92-9)
EPA chemische Informationen: 2 · 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)- (2180-92-9)

Sicherheit und Regulatorisches

Sicherheitsdaten

ridadr: 2811
risk_code: 26/27/28-38-41
hazard_code: T+
safety_code: 22-26-36/37/39-45

Chemie und Industrie

Pharmakologische Informationen

ATC CodeN01BB01

Cellular LocationsExtracellular

Metabolite PathwaysBupivacaine Action Pathway

Verwendung und Herstellung

Use ClassificationPharmaceuticals

Anwendungen · 1 Eintrag

VerwendenLike 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.