UCSF

ZINC01530814

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
October 6th, 2004 21 Yes

Popular Name: Bupivacaine hydrochloride Bupivacaine hydrochloride

Find On: PubMed — Wikipedia — Google

CAS Numbers: 14252-80-3 , 14252-80-3, 2180-92-9 [bu , 14252-80-3, 2180-92-9 [bupivacaine], 18010-40-7 [anhydrous] , 18010-40-7 , 2180-92-9 , 27262-45-9 , 27262-48-2 , 38396-39-3 , [14252-80-3] , [18010-40-7] , [2180-92-9] , [38396-39-3]

Other Names:

( inverted exclamation markA)-bupivacaine

(+-)-Bupivacaine

(+-)-Bupivacaine hydrochloride; 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride; 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride; 2',6'-Pipecoloxylidide, 1-butyl-, monohydrochloride; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethy

(+-)-Bupivacaine; (+-)-bupivacaine; (RS)-bupivacaine; 1-Butyl-2',6'-pipecoloxylidide; 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; Bupivacaine; Carbostesin; DL-Bupivacaine; dl-1-Butyl-2',6'-pipecoloxylidide; racemic bupivacaine

(+-)-Bupivacaine; (1)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; 1-Butyl-2',6'-pipecoloxylidide; 2',6'-Pipecoloxylidide, 1-butyl-; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylpheny

(+-)-Bupivacaine;Bloqueina;Bupivacaina [INN-Spanish];Bupivacaine HCL;Bupivacaine HCL KIT;Bupivacainum [INN-Latin];CBupivacaine;DL-Bupivacaine;DUR-843;LAC-43

(+/-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride, monohydrate; 1-butyl-2',6'-pipecoloxylidide monohydrochloride monohydrate; 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride hydrate; bupivacaine hydrochloride; bupivacaine hydroch

(1)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

(R)-(+)-bupivacaine

(R)-Bupivacaine HCl

-BUPIVACAINEHCL

caine

1-Butyl-2',6'-pipecoloxylidide

1-butyl-2-piperidylformo-2',6'-xylidide hydrochloride; 1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride; bupivacaine HCl; bupivacaine hydrochloride; bupivacaine monohydrochloride

1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide

1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

1-Butyl-piperidine-2-carboxylic acid (2,6-dimethyl-phenyl)-amide

14252-80-3; Bupivacaine hydrochloride (USP); Bupivacaine hydrochloride hydrate (JP16); D01450; Marcaine (TN)

15233-43-9

18010-40-7; Bupivacaine hydrochloride; Prestwick_894

2',6'-Pipecoloxylidide, 1-butyl-

2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride, (+)-; Bupicaine hydrochloride (+); LS-109845

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (+-)-

2180-92-9

2180-92-9; Bucaine (TN); Bupivacaine (USAN/INN); D07552; Exparel (TN)

38396-39-3

AB00053674

AC-2096

AC1L1DRE

AC1Q5LX4

AH 250

AKOS001637202

Anekain

AR-1A0242

Bio-0886

Bloqueina

BPBio1_000298

BRD-A01636364-003-05-2

BRD-A01636364-003-08-6

BSPBio_000270

BSPBio_002607

Bucaine

Bucaine (TN)

Bupivacaina

Bupivacaina [INN-Spanish]

bupivacaina; bupivacaine; bupivacainum

Bupivacaine

Bupivacaine (BAN

Bupivacaine (hydrochloride)

Bupivacaine (INN)

Bupivacaine Carbonate

BUPIVACAINE HCL

Bupivacaine HCL KIT

bupivacaine hydrochloride (anhydrous)

Bupivacaine hydrochloride (Marcain)

bupivacaine hydrochloride hydrate

Bupivacaine Monohydrochloride, Monohydrate

Bupivacaine [INN:BAN]

Bupivacaine; C07529; Marcaine

bupivacainehydrochloride

Bupivacainum

Bupivacainum [INN-Latin]

Bupivan

C07529

C18H28N2O

Carbostesin

cBupivacaine

CHEBI:250882

CHEBI:3215

CHEMBL1098

Chirocaine

CID2474

D07552

DAP001229

DB00297

DepoBupivacaine

DivK1c_000758

dl-1-Butyl-2',6'-pipecoloxylidide

DL-Bupivacaine

DUR-843

Duracaine

EINECS 218-553-3

EINECS 253-911-2

Exparel

FDA

HMS2090F12

IDI1_000758

INN

INN); Bupivacaine HCl (FDA

JAN

KBio1_000758

KBio2_002004

KBio2_004572

KBio2_007140

KBio3_001827

KBioGR_001516

KBioSS_002004

KST-1A4609

L000695

LAC-43

Levobupivacaine hydrochloride

LS-109841

LS-190233

LS-2222

Marcain, Marcaine, Sensorcaine, Vivacaine

Marcaina

Marcaine

Marcaine HCL

Marcaine Spinal

Meaverin-ultra

MFCD00078956

MFCD00243007

MFCD00864438

MLS001361336

MolPort-004-955-820

NA

Narcain

NCGC00178579-01

NCGC00178579-02

NINDS_000758

NSC119660

Prestwick0_000305

Prestwick1_000305

Prestwick2_000305

Prestwick3_000305

QA-7167

Sensorcaine

Sensorcaine-MPF

Sensorcaine-MPF Spinal

SKY-0402; LAC-43; WIN-11318

SKY0402

SMR000058218

SPBio_001558

SPBio_002489

Spectrum2_001589

Spectrum3_000974

Spectrum4_001098

Spectrum5_001483

Spectrum_001524

Svedocain

Transdur-Bupivacaine

UNII-Y8335394RO

USAN

USAN)

USAN); Bupivacaine HCl (FDA

USAN); Bupivacaine Hydrochloride (FDA

USP

USP)

Win 11318

Win 11318 HCl

WIN-11318

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 3.34 10.3 -35.63 2 3 1 34 289.443 5 ↓

Vendor Notes

Note Type Comments Provided By
mechanism . ZereneX Building Blocks
ALOGPS_SOLUBILITY 9.77e-02 g/l DrugBank-approved
Purity 95% Fluorochem
Purity >95% Fluorochem
Therapy anesthetic (local) SMDC Iconix
mechanism Blocks the generation and the conduction of nerve impulses, IBScreen Bioactives
PUBCHEM_PATENT_ID EP0757555A1; EP0914441A2; EP0920522A1; EP0963202A1; US5149320; US5209724; US5226901; US5261903; US5610184; US5760077; US6046187; WO1997040165A1; WO1998006863A1; WO1998010769A1; WO1999062581A2; WO2000009145A1 IBM Patent Data
Patent Database Links EP1405646; EP1559418; EP1576953; EP1586347; EP1685843; EP1702597; EP1712220; EP1762236; EP1772767; EP1813295; EP1815846; EP1829527; EP1829528; EP1834627; EP1894559; EP1902705; EP1972684; EP1990639; US2004068007; US2004254182; US2007189977; US2007189978; U ChEBI
biological_use Local anaesthetic IBScreen Bioactives
Indications local anesthetic KeyOrganics Bioactives
Target Others Selleck Chemicals
mechanism presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential IBScreen Bioactives
Target Sodium Channel Selleck Chemicals

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
SCN1A-1-E Sodium Channel Protein Type I Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 5400 0.35 Binding ≤ 10μM
SCN2A-1-E Sodium Channel Protein Type II Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 5400 0.35 Binding ≤ 10μM
SCN3A-1-E Sodium Channel Protein Type III Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 5400 0.35 Binding ≤ 10μM
SCN8A-1-E Sodium Channel Protein Type VIII Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 5400 0.35 Binding ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
SCN1A_HUMAN P35498 Sodium Channel Protein Type I Alpha Subunit, Human 5400 0.35 Binding ≤ 10μM
SCN2A_HUMAN Q99250 Sodium Channel Protein Type II Alpha Subunit, Human 5400 0.35 Binding ≤ 10μM
SCN3A_HUMAN Q9NY46 Sodium Channel Protein Type III Alpha Subunit, Human 5400 0.35 Binding ≤ 10μM
SCN8A_HUMAN Q9UQD0 Sodium Channel Protein Type VIII Alpha Subunit, Human 5400 0.35 Binding ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Interaction between L1 and Ankyrins

Analogs ( Draw Identity 99% 90% 80% 70% )