INDIGOTINDISULFONIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H10N2O8S2
Molecular Weight	422.389
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=C2N\C(C(=O)C2=C1)=C3\NC4=CC=C(C=C4C3=O)S(O)(=O)=O

InChI

InChIKey=CFZXDJWFRVEWSR-BUHFOSPRSA-N

InChI=1S/C16H10N2O8S2/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)/b14-13+

HIDE SMILES / InChI

Description
Sources: http://www.jmig.org/article/S1553-4650(14)01740-3/pdf | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6f0dfc8-63b1-4bc1-96eb-3cd0c3d5d4c2

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

Condition	Modality	Targets	Highest Phase	Product
Bladder conditions 2 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6f0dfc8-63b1-4bc1-96eb-3cd0c3d5d4c2	Diagnostic		Approved 8429	INDIGO CARMINE Approved Use Originally employed as a kidney function test, the chief application of Indigo Carmine at present is localizing ureteral orifices during cystoscopy and ureteral catheterization.

PubMed

Title	Date	PubMed
REFINEMENT OF COLORIMETRIC METHODS WITH SPECIAL REFERENCE TO INDIGO CARMINE AS A FUNCTIONAL TEST: A PRELIMINARY REPORT.	1920 Feb	18738104
The use of indigo carmine for dye dilution curves.	1955 Nov	13270370
Extensive skin color change caused by extravasation of indigo carmine.	2012 May	22679552
High-definition vs. standard-definition endoscopy with indigo carmine for the in vivo diagnosis of colonic polyps.	2013 Dec	24917993
Profound hypotension after an intradermal injection of indigo carmine for sentinel node mapping.	2013 Mar	23593094
Microdochectomy assisted by ultrasound-guided indigo carmine staining of intraductal lesions: a case report.	2014 Jun	25013442
Case of Wenckebach-type atrioventricular block caused by administration of indigo carmine.	2014 Mar 20	24733592
TiO2 immobilized on Manihot carbon: optimal preparation and evaluation of its activity in the decomposition of indigo carmine.	2015 Jan 12	25588214
Clinical impact of dual red imaging in colorectal endoscopic submucosal dissection: a pilot study.	2016 Sep	27582880
A Third Surgically Managed Ectopic Pregnancy after Two Salpingectomies Involving the Opposite Tube.	2017	28116193
The detection of sentinel lymph nodes in laparoscopic surgery for uterine cervical cancer using 99m-technetium-tin colloid, indocyanine green, and blue dye.	2017 Mar	27894166

Patents

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.

Name

Type

Language

INDIGOTINDISULFONIC ACID

Common Name

English

INDIGOTINDISULFONATE

Common Name

English

SAXON BLUE

Common Name

English

1H-INDOLE-5-SULFONIC ACID, 2-(1,3-DIHYDRO-3-OXO-5-SULFO-2H-INDOL-2-YLIDENE)-2,3-DIHYDRO-3-OXO-

Common Name

English

BLUE X

Common Name

English

5,5'-INDIGOTINDISULFONIC ACID

Common Name

English

INDIGO CARMINE ACID

Common Name

English

NSC-8646

Code

English

Code System Code Type Description

CHEBI

90117