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=CC2=C(N\C(C2=O)=C3\NC4=C(C=C(C=C4)S(O)(=O)=O)C3=O)C=C1

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 8583	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.

Doses

Dose	Population	Adverse events
80 mg single, intravenous Higher than recommended Dose: 80 mg Route: intravenous Route: single Dose: 80 mg Sources: https://pubmed.ncbi.nlm.nih.gov/841782/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/841782/	Other AEs: Hypertension... Other AEs: Hypertension (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/841782/
40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/	Other AEs: Hypotension, Bronchospasm... Other AEs: Hypotension (grade 3) Bronchospasm (grade 3) Urticaria (grade 3) Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/
40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18835972/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18835972/	Other AEs: Atrioventricular block... Other AEs: Atrioventricular block Sources: https://pubmed.ncbi.nlm.nih.gov/18835972/

AEs

AE	Significance	Dose	Population
Hypertension	grade 3	80 mg single, intravenous Higher than recommended Dose: 80 mg Route: intravenous Route: single Dose: 80 mg Sources: https://pubmed.ncbi.nlm.nih.gov/841782/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/841782/
Bronchospasm	grade 3	40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/
Hypotension	grade 3	40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/
Urticaria	grade 3	40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8048206/
Atrioventricular block		40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18835972/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18835972/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 UGT2B7 197 UGT1A6 136 CYP19A1 429 P-gp 1741	P-gp 2052 CYP2A6 626 UGT1A6 343 UGT2B7 456

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results	no [IC50 >1000 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results	no [IC50 >1000 uM]
UGT1A6 171	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results	no [IC50 >2000 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results	no [IC50 >2000 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results Page: 39.0	no
CYP2A6 911	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results	yes [IC50 50 uM]

Drug as victim

Target	Modality	Activity
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20041016/	no
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3705#section=BioAssay-Results Page: 41 \| 45	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20041016/	no
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20041016/	no

PubMed

Title	Date	PubMed
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

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

NSC-8646

Preferred 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

Code System Code Type Description

CHEBI

90117