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Details

Stereochemistry ACHIRAL
Molecular Formula C16H8N2O8S2.2Na
Molecular Weight 466.353
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of INDIGOTINDISULFONATE SODIUM

SMILES

[Na+].[Na+].[O-]S(=O)(=O)C1=CC=C2N\C(C(=O)C2=C1)=C3\NC4=C(C=C(C=C4)S([O-])(=O)=O)C3=O

InChI

InChIKey=KHLVKKOJDHCJMG-QDBORUFSSA-L
InChI=1S/C16H10N2O8S2.2Na/c19-15-9-5-7(27(21,22)23)1-3-11(9)17-13(15)14-16(20)10-6-8(28(24,25)26)2-4-12(10)18-14;;/h1-6,17-18H,(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b14-13+;;

HIDE SMILES / InChI

Molecular Formula C16H8N2O8S2
Molecular Weight 420.373
Charge -2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Indigotindisulfonic acid (also known as Indigo carmine) is a synthetic dye discovered in 18th century. It is used in many countiries as a food colorant and a pH indicator. In medicine the dye is used to localize ureteral orifices during cystoscopy and ureteral catheterization. In June 2014 the FDA announced the shortage of indigotindisulfonic acid.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
INDIGO CARMINE

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Indigotindisulfonic acid (Indigo Carmine) solution is injected either by the intravenous or intramuscular route, and its appearance at the ureteral orifices is watched with the cystoscope in place.
Route of Administration: Other
In Vitro Use Guide
Human chondrocytes grown on 6-well plates to 80% subconfluence were incubated with different concentrations of indigotindisulfonic acid (1, 10 and 100% solution) for 5 and 10 minutes. Human chondrocytes treated with solutions of 100% solution showed increased number of cells with defect cell structure. Chondrocytes showed loss of cell contacts after an incubation time of 10 minutes as revealed by light microscopy.
Substance Class Chemical
Record UNII
D3741U8K7L
Record Status Validated (UNII)
Record Version