OMOCIANINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H35N2O12S4.3H
Molecular Weight	770.91
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H+].[H+].[H+].CC(\C=C\C=C1\N(CCS([O-])(=O)=O)C2=C(C=C(C=C2)S([O-])(=O)=O)C1(C)C)=C/C=C/C3=[N+](CCS([O-])(=O)=O)C4=CC=C(C=C4C3(C)C)S([O-])(=O)=O

InChI

InChIKey=WKWHOLCUESSZIQ-UHFFFAOYSA-N

InChI=1S/C32H38N2O12S4/c1-22(8-6-10-29-31(2,3)25-20-23(49(41,42)43)12-14-27(25)33(29)16-18-47(35,36)37)9-7-11-30-32(4,5)26-21-24(50(44,45)46)13-15-28(26)34(30)17-19-48(38,39)40/h6-15,20-21H,16-19H2,1-5H3,(H3-,35,36,37,38,39,40,41,42,43,44,45,46)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19798535 | https://adisinsight.springer.com/drugs/800021549

Omocianine was developed as an enhancer of fluorescence optical mammography allowed better detection of more superficially located lesions. It was shown that the lowest doses of omocianine performed best in lesion detection. Diffuse optical tomography using a low-dose fluorescent agent is feasible and safe for breast cancer visualization in patients. This compound participated in phase I clinical trials in Germany and in the Netherlands, however, these studies were discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Near-infrared imaging of breast cancer using optical contrast agents.	2012-11	23132668
Near-infrared imaging of the breast using omocianine as a fluorescent dye: results of a placebo-controlled, clinical, multicenter trial.	2011-11	21788905
A novel fluorescent imaging agent for diffuse optical tomography of the breast: first clinical experience in patients.	2010-06	19798535

Sample Use Guides

In Vivo Use Guide

Eleven women suspected of breast cancer were imaged with diffuse optical tomography at multiple time points (up to 24 h) after receiving an intravenous injection of Omocianine (doses 0.01 to 0.1 mg/kg bodyweight).

Route of Administration: Intravenous

Name

Type

Language

OMOCIANINE

Official Name

English

TRIHYDROGEN 2-((1E,3E,5E)-7-((2E)-3,3-DIMETHYL-5-SULFONATO-1-(2-SULFONATOETHYL)-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)-4-METHYLHEPTA-1,3,5-TRIENYL)-3,3-DIMETHYL-1-(2-SULFONATOETHYL)-3H-INDOLIUM-5-SULFONATE

Preferred Name

English

omocianine [INN]

Common Name

English

TRIHYDROGEN 2-((1E,3E,5E)-7-((2E)-3,3-DIMETHYL-5-SULPHONATO-1-(2-SULPHONATOETHYL)-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)-4-METHYLHEPTA-1,3,5-TRIENYL)-3,3-DIMETHYL-1-(2-SULPHONATOETHYL)-3H-INDOLIUM-5-SULPHONATE

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C166847