IPRAVACAINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H26N2O
Molecular Weight	286.4118
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(C)=C1NC(=O)C2CCCCN2CC3CC3

InChI

InChIKey=DNUYDQISHIJMLD-UHFFFAOYSA-N

InChI=1S/C18H26N2O/c1-13-6-5-7-14(2)17(13)19-18(21)16-8-3-4-11-20(16)12-15-9-10-15/h5-7,15-16H,3-4,8-12H2,1-2H3,(H,19,21)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11160646 | https://www.ncbi.nlm.nih.gov/pubmed/11009240

IPRAVACAINE is a long-acting local anesthetic which anesthetic potency is similar to that of bupivacaine. It blocks the open state of human cardiac K+ channels.

Originator

Approval Year

PubMed

Title	Date	PubMed
Ulnar nerve block induced by the new local anesthetic IQB-9302 in healthy volunteers: a comparison with bupivacaine.	2001-11	11682422
Effects of bupivacaine and a novel local anesthetic, IQB-9302, on human cardiac K+ channels.	2001-02	11160646
Stereoselective effects of the enantiomers of a new local anaesthetic, IQB-9302, on a human cardiac potassium channel (Kv1.5).	2001-01	11159686
Antinociceptive and motor-blocking action of epidurally administered IQB-9302 and bupivacaine in the dog.	2000-09-29	11009240

Sample Use Guides

In Vitro Use Guide

The effects of the ipravacaine (IQB-9302) enantiomers were studied on human Kv1.5 channels stably expressed in LTK- cells using the whole-cell configuration of the patch-clamp technique. Block induced by IQB-9302 was stereoselective with the R(+) enantiomer being 3.2-fold more potent than the S(-) one (Kd of 17.8+/-0.5 microM vs 58.6+/-4.0 microM).

Name

Type

Language

IPRAVACAINE

Official Name

English

ipravacaine [INN]

Preferred Name

English

(2RS)-1-(CYCLOPROPYLMETHYL)-2',6'-DIMETHYL-2-PIPERIDINECARBOXANILIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245