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Indigotindisulfonic acid

HCID 3705
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
483-20-5
Standard SMILES
O=C1C(c2[nH]c3ccc(S(=O)(=O)O)cc3c2O)=Nc2ccc(S(=O)(=O)O)cc21
InChIKey
CFZXDJWFRVEWSR-UHFFFAOYSA-N
Molecular formula
C16H10N2O8S2
Average molar mass
422.4 g/mol
Monoisotopic mass
421.98785763

Overview

Indigo carmine (acid form) is a member of the class of indolones obtained by formal 2,2'-oxidative coupling of two molecules of 3-oxo-2,3-dihydroindole-5-sulfonic acids. It has a role as a histological dye and a food colouring. It is a member of indolones, an arenesulfonic acid, a ring assembly, an enone and an olefinic compound. It is a conjugate acid of an indigo carmine(2-).

Names & identifiers

Preferred name
Indigotindisulfonic acid
IUPAC
2-(3-hydroxy-5-sulfo-1H-indol-2-yl)-3-oxoindole-5-sulfonic acid
English name
2-(1,3-dihydro-3-oxo-5-sulpho-2H-indol-2-ylidene)-3-oxoindoline-5-sulphonic acid
Molecular formula
C16H10N2O8S2
Molecular weight
422.39

Names & synonyms

INDIGOTINDISULFONIC ACIDIndigotindisulfonateSaxon blueBlue X5,5'-Indigotindisulfonic acid483-20-5Indigo carmine acid2-(1,3-Dihydro-3-oxo-5-sulpho-2H-indol-2-ylidene)-3-oxoindoline-5-sulphonic acidDTXSID0044288Indigotin Iindigo carmine free acidNSC-8646
Show more names
indigo carmine (acid form)2-(1,3-Dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro-3-oxo-1H-indole-5-sulfonic acid1H-Indole-5-sulfonic acid, 2-(1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro-3-oxo-
X7OI7JF73Pindigo-5,5'-disulfonic acid3,3'-dioxo-[2,2'-biindolinylidene]-5,5'-disulfonic acidIndigo Carmine Disodium SaltSachsischblauMurabbaIndigotine LakeSoluble Indigo

Database identifiers

CAS
483-20-5
PubChem CID
3705
DTXSID
DTXSID0044288

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
191 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
9
Rotatable bonds
3
Heavy atoms
28
Formal charge
0
Complexity
904

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP-2.0
Solubility0.1-1g/100ml
Melting Point>300

Physicochemical properties

FDA UNII
7 OI7JF73P · X7OI7JF73P

Chemistry & industry

Pharmacology

Protein BindingThe protein binding of indigotindisulfonate sodium _in vitro_ is approximately 90%.
Pharmacodynamics · 1 item

Approximately 4-9 minutes after indigotindisulfonate sodium is administered intravenously, its blue color is detectable at the ureteral orifices, enabling easier visualization for accuracy during medical procedures. Although indigotindisulfonic acid and its salt form indigotindisulfonate sodium were initially acknowledged as pharmacologically inert, their use has been associated with cardiovascular effects. Indigotindisulfonate sodium may lead to transient alpha-receptor stimulation, manifested as increased total peripheral vascular resistance, increased diastolic and systolic blood pressure, and increased central venous pressure with decreased cardiac output, stroke volume and heart rate. The use of indigotindisulfonate sodium may lead to severe or life-threatening cardiovascular reactions such as cardiac arrest, arrhythmia, asystole, second-degree atrioventricular block, hypotension, elevation in blood pressure, bradycardia, and tachycardia. Serious anaphylactic reactions with hypotension, dyspnea, bronchospasm, urticaria, or erythema have also been reported. Also, the use of indigotindisulfonate sodium may interfere with light absorption and pulse oximetric methods.

Mechanism of Action · 1 item

Indigotindisulfonic acid is a biologically inert blue dye. After intravenous injection, indigotindisulfonic acid is excreted by the kidney through tubular secretion and, with its deep blue color, it enhances visualization of the ureteral orifices. Because of this, indigotindisulfonic acid is used to identify ureteral patency in urologic and gynecologic procedures. Indigotindisulfonic acid may lead to the development of hypertension. It has been suggested that indigotindisulfonic acid inhibits endothelium-dependent relaxation at the level of nitric oxide generation and/or its release from the endothelium. Also, indigotindisulfonic acid appears to inhibit vascular guanylyl cyclase in smooth muscle.

Biological Half-LifeIn healthy adults given 5 ml of indigotindisulfonate sodium, the elimination half-life was 12 minutes.
Metabolism/Metabolites · 1 item

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL1091250
ChEBI
CHEBI:90117
UNII
X7OI7JF73P
EC Number
207-593-7
Nikkaji
J28.074G、J28.075E、J5.986B

Indigotindisulfonate sodium is mainly oxidized via primary metabolic pathways. An _in vivo_ study done in rats showed that the breakdown of indigotindisulfonate sodium (FD&C Blue No. 2) generated two products: isatin-5-sulphonic acid and 5-sulphoanthranilic acid. Clinical studies evaluating indigotindisulfonate sodium metabolism products have not been performed.

Absorption, Distribution and Excretion · 4 items

In healthy adults given 5 ml of indigotindisulfonate sodium (salt form of indigotindisulfonic acid), the Cmax and AUC0-INF were 6.33 μg/mL and 1.15 μg·h/mL, respectively. Studies evaluating the pharmacokinetic properties of intravenous indigotindisulfonate sodium in patients with renal impairment have not been performed. Based on subgroup analyses in a randomized clinical trial, patients with mild to moderate renal impairment or an estimated glomerular filtration rate (eGFR) from 30 to 89 mL/min do not require dose adjustments. Indigotindisulfonate sodium is not recommended in patients with eGFR lower than 30 mL/min.

Indigotindisulfonic acid is excreted largely by the kidneys, retaining its blue color during passage through the body. Approximately 16% of the unchanged drug is excreted in urine, and less than 2% is excreted in feces. The elimination of this dye begins rapidly after injection, appearing in the urine within 5 minutes.

The volume of distribution of indigotindisulfonate sodium is 10.7 L.

In healthy adults given 5 ml of indigotindisulfonate sodium, the mean urinary clearance was 7.08 L/hour, and the mean total clearance was 40.2 L/hour.

Applications

UsesDiagnostic aid (cystoscopy).

Suppliers1 total

陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of indolones obtained by formal 2,2'-oxidative coupling of two molecules of 3-oxo-2,3-dihydroindole-5-sulfonic acids.