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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 of INDIGOTINDISULFONIC ACID

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
Molecular Formula C16H10N2O8S2
Molecular Weight 422.389
Charge 0
Count
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

1950
105
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

UGT2B7
197

UGT1A6
136

CYP19A1
429

P-gp
1741
P-gp
2052

CYP2A6
626

UGT1A6
343

UGT2B7
456
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
2633
 no [IC50 >1000 uM]
P-gp
1932
 no [IC50 >1000 uM]
UGT1A6
171
 no [IC50 >2000 uM]
UGT2B7
210
 no [IC50 >2000 uM]
CYP19A1
430
 no
CYP2A6
911
 yes [IC50 50 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
626
 no
P-gp
2052
 no
UGT1A6
343
 no
UGT2B7
456
 no
PubMed

PubMed

TitleDatePubMed
The detection of sentinel lymph nodes in laparoscopic surgery for uterine cervical cancer using 99m-technetium-tin colloid, indocyanine green, and blue dye.
2017-03
A Third Surgically Managed Ectopic Pregnancy after Two Salpingectomies Involving the Opposite Tube.
2017
Clinical impact of dual red imaging in colorectal endoscopic submucosal dissection: a pilot study.
2016-09
TiO2 immobilized on Manihot carbon: optimal preparation and evaluation of its activity in the decomposition of indigo carmine.
2015-01-12
Microdochectomy assisted by ultrasound-guided indigo carmine staining of intraductal lesions: a case report.
2014-06
Case of Wenckebach-type atrioventricular block caused by administration of indigo carmine.
2014-03-20
High-definition vs. standard-definition endoscopy with indigo carmine for the in vivo diagnosis of colonic polyps.
2013-12
Profound hypotension after an intradermal injection of indigo carmine for sentinel node mapping.
2013-03
Extensive skin color change caused by extravasation of indigo carmine.
2012-05
The use of indigo carmine for dye dilution curves.
1955-11
REFINEMENT OF COLORIMETRIC METHODS WITH SPECIAL REFERENCE TO INDIGO CARMINE AS A FUNCTIONAL TEST: A PRELIMINARY REPORT.
1920-02
Patents

Patents

20030064146
2
20050198746
8

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
Created
by admin
on Mon Mar 31 18:06:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:15 GMT 2025
Record UNII
X7OI7JF73P
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
RXCUI
1546441
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
PUBCHEM
5282430
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
NSC
8646
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
DAILYMED
X7OI7JF73P
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID0044288
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
CAS
483-20-5
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
FDA UNII
X7OI7JF73P
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-593-7
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
RXCUI
325514
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
ALTERNATIVE
DRUG BANK
DB11577
Created by admin on Mon Mar 31 18:06:15 GMT 2025 , Edited by admin on Mon Mar 31 18:06:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of INDIGOTINDISULFONATE SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of INDIGOTINDISULFONIC ACID
ACTIVE MOIETY
NIH
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