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Home > Encyclopedia > Indocyanine green

Indocyanine green

pharmaceutical raw materials
Indocyanine green structure

Indocyanine green 

structure
  • CAS No:

    3599-32-4

  • Formula:

    C43H48N2O6S2.Na

  • Chemical Name:

    Indocyanine green

  • Synonyms:

    1H-Benz[e]indolium,2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrien-1-yl]-1,1-dimethyl-3-(4-sulfobutyl)-,inner salt,sodium salt (1:1);1H-Benz[e]indolium,2-[7-[1,1-dimethyl-3-(4-sulfobutyl)benz[e]indolin-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,hydroxide,inner salt,sodium salt;1H-Benz[e]indolium,2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,hydroxide,inner salt,sodium salt;1H-Benz[e]indolium,2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,inner salt,sodium salt;ICG;Indocyanine green;Cardio Green;Wofaverdin;Indocyanin green;Ujoviridin;HWD Indocyanine Green;4,5-Benzoindotricarbocyanine;IR 125;NK 2611;NK 2612;Opthagreen;SO 270;58984-23-9;1814902-08-3

  • Categories:

    Active Pharmaceutical Ingredients  >  Diagnostic Agents

Description

Cardiogreen is a low toxicic fluorescent agent that has been widely used in medical diagnostics, such as determining cardiac output, hepatic function, and liver blood flow, and for ophthalmic angiography.


A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.

Indocyanine green Basic Attributes

774.96

774.277344

222-751-5

DTXSID2023145

DARK GREEN, BLUE-GREEN, OLIVE BROWN, DARK BLUE, OR BLACK POWDER, SOLN ARE DEEP EMERALD-GREEN IN COLOR

V - Various

32129000

Characteristics

137

Log Kow= -0.29 at pH 7.4

Green-bronze Powder

235 °C

157ºC

H2O: soluble 1mg/mL

Amber Vial, Refrigerator

Intravenous-rat LD50: 87 mg/kg; Intravenous-mouse LD50: 60 mg/kg

Thermal decomposition releases toxic nitrogen oxides, sulfur oxides, sodium oxide fumes

ODORLESS OR WITH SLIGHT ODOR

PH (1 IN 200 SOLN) ABOUT 6

Safety Information

NONH for all modes of transport

3

36/37/38

26-36-37/39

DE3150000

Xi

The warehouse is low-temperature, ventilated and dry

UNSTABLE IN SOLN.

P261-P305 + P351 + P338

H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Schlanz KD et al; Clin Pharmacokinet 21 (5): 344-56 (1991). A review is presented of the mechanism by which calcium antagonists alter the pharmacokinetics of other drugs, including antipyrine and indocyanine green. ...

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

highly

INCR IN HEPATIC EXCRETORY FUNCTION HAS BEEN OBSERVED AFTER PRETREATMENT WITH SOME DRUGS. FOR EXAMPLE, PHENOBARBITAL HAS BEEN DEMONSTRATED TO INCR PLASMA DISAPPEARANCE & BILIARY EXCRETION OF...INDOCYANINE GREEN...|SUPPRESSION OF BILIARY SECRETION OF INDOCYANINE GREEN...BY PRETREATMENT WITH SKF 525-A WAS SHOWN TO BE DUE TO TEMP EFFECT RATHER THAN TO EFFECT ON HEPATIC ENDOPLASMIC RETICULUM.|INDOCYANINE GREEN DECR INITIAL RATE OF UPTAKE OF OUABAIN IN RAT LIVER CELLS BY MORE THAN 50%. DATA INDICATE THAT CMPD MAY ENTER LIVER CELLS BY PROCESS SIMILAR TO ACTIVE CARRIER-MEDIATED TRANSPORT.|IN MALE RATS INJECTED IV WITH 1.0 MG/KG MERCURY, INDOCYANINE GREEN INHIBITED BILIARY EXCRETION OF METHYLMERCURY.|For more Interactions (Complete) data for INDOCYANINE GREEN (13 total), please visit the HSDB record page.

Drug Information

Dyes|TO DETERMINE CARDIAC OUTPUT, HEPATIC FUNCTION, & LIVER BLOOD FLOW. FOR HEPATIC FUNCTION STUDIES, CALCULATED AMT OF DIAGNOSTIC AGENT IS INJECTED INTO ARM VEIN. 20 MIN AFTER INJECTION, 6 ML OF VENOUS BLOOD IS WITHDRAWN FROM OPPOSITE ARM. AFTER COAGULATION & CENTRIFUGATION, CLEAR SERUM IS READ IN PHOTOMETER @ 800-810 NM.|DYE RETENTION OF LESS THAN 4% IS FOUND IN HEALTHY SUBJECTS. ... FAILURE TO REMOVE DYE, AS INDICATED BY SERUM LEVELS IN EXCESS OF 4%, IS INDICATIVE OF IMPAIRED HEPATIC FUNCTION.|USUAL, IV, BLOOD VOL DETERMINATION, 5 MG IN 1 ML; HEPATIC FUNCTION DETERMINATION, 0-5 MG/KG.|DYE IS STABLE IN PLASMA & WHOLE BLOOD PERMITTING LATER ANALYSIS. USERS VARY BOTH CONCN & DOSAGE. IN MAN TOTAL DOSAGE HAS NORMALLY BEEN BELOW 2 MG/KG.

...CONTAINS SMALL AMT OF /5%/ SODIUM IODIDE; THUS, IT SHOULD BE USED WITH CAUTION IN PT ALLERGIC TO IODIDES & RADIOACTIVE IODINE UPTAKE STUDIES SHOULD NOT BE PERFORMED FOR AT LEAST 1 WK FOLLOWING ITS USE. SINCE PROBENECID HAS BEEN SHOWN IN DOGS TO AFFECT HEPATIC UPTAKE, THIS POSSIBILITY SHOULD BE KEPT IN MIND.|SAFE USE OF THIS DRUG IN PREGNANCY HAS NOT BEEN ESTABLISHED.|USE FRESH SOLN ONLY AS RECOMMENDED.

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

FOLLOWING IV INJECTION, INDOCYANINE GREEN IS RAPIDLY BOUND TO PLASMA PROTEIN, QUICKLY REMOVED FROM CIRCULATION BY LIVER, & EXCRETED IN BILE IN UNCONJUGATED FORM.|WITH INDOCYANINE GREEN, IT HAS BEEN SHOWN THAT RAT HAS HIGHER MAX BILIARY EXCRETION RATE (0.065 MG/KG/MIN) THAN DOES RABBIT (0.05 MG/KG/MIN) OR DOG (0.027 MG/KG/MIN).|T/2 INCR WITH INCR DOSAGE. ... CONSIDERABLE DIFFERENCE HAS BEEN NOTED BETWEEN NORMAL MONGRELS & PUREBRED BEAGLES IN CLEARANCE TIMES.|APPARENT HEPATIC EXTRACTION OF INDOCYANINE GREEN IN RATS WAS SURPRISINGLY LOW @ DOSES ABOVE 1 MG/KG. CHANGES IN HEPATIC BLOOD FLOW WOULD NOT ALTER CLEARANCE.|For more Absorption, Distribution and Excretion (Complete) data for INDOCYANINE GREEN (10 total), please visit the HSDB record page.

...INDOCYANINE GREEN...APPEARS IN BILE UNCHANGED

...COMMERCIAL PRODUCT CONTAINS MOISTURE & ABOUT 5% SODIUM IODIDE AS CONTAMINANT.

VERY LOW INCIDENCE OF SIDE EFFECTS. EXTRAVASATION OF DYE APPEARS TO CAUSE NO ADVERSE EFFECTS...ALLERGIC REACTIONS /RARE/. DIAPHORESIS, PRURITUS, & HEADACHE IN 2 UREMIC PATIENTS...ANAPHYLACTOID SHOCK /1 UREMIC PATIENT. ADVERSE EFFECT, IV, IA, INTRA-CARDIAC/|SODIUM IODIDE PRESENT IN...INDOCYANINE GREEN...REPORTED TO CAUSE INCREASE IN SERUM INORGANIC IODIDE LEVELS. /DRUG/ MAY CAUSE TRANSIENT ELEVATION IN SERUM UNCONJUGATED BILIRUBIN, PROBABLY DUE TO COMPETITION BETWEEN DYE & BILIRUBIN FOR BILIARY EXCRETION /ADVERSE EFFECT, IV, IA, INTRA-CARDIAC/|... Although adverse reactions to indocyanine green are known to occur, the dye has been used for more than 30 yr in tests of cardiac and hepatic function, with a high level of safety. Improved digital video technology has renewed interest in the use of iv indocyanine green in ophthalmic imaging. This report describes the /investigators/ experience regarding the safety of /this dye/ for digital angiography and their recommendation for its use in the ophthalmic setting. Digital indocyanine green videoangiography was performed in 1226 consecutive patients, and 1923 indocyanine green videoangiography tests were performed. A registry of adverse reactions to /this dye/ was established. Criteria were used to define mild, moderate and severe adverse reactions, and these data were recorded for every ICG study performed. There were three (0.15%) mild adverse reactions, four (0.2%) moderate reactions and one (0.5%) severe adverse reaction. There were no deaths. ... This study documents the safety of indocyanine green for use in ophthalmic videoangiography.

Cardio Green

Indocyanine green Use and Manufacturing

Methods of Manufacturing

HESELTINE, BROOKER, US PATENT 2,895,955 (1959 TO KODAK).|Indocyanine Green may be prepared by reacting 1,1,2-trimethyl-3-(4-sulfobutyl)-1H-benz(e)indolium hydroxide inner salt (I) with a bis(Schiff base) derived from glutaconic aldehyde. Acetic anhydride is used to favor the condensation and the acidic dye is ultimately neutralized with sodium hydroxide.

Uses

In infrared photography; in preparation of Wratten filters. Diagnostic drug for liver function determination, IR laser dye.

STERILE USP: 10, 25, 40, & 50 MG.

1H-Benz[e]indolium, 2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrien-1-yl]-1,1-dimethyl-3-(4-sulfobutyl)-, inner salt, sodium salt (1:1): ACTIVE

DETERMINATION OF CYANINE DYES BY THIN-LAYER CHROMATOGRAPHY.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:775.0
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:12
Exact Mass:774.27732385
Monoisotopic Mass:774.27732385
Topological Polar Surface Area:137
Heavy Atom Count:54
Complexity:1520
Undefined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Diagnostic drug used to check liver function and effective liver blood flow. After intravenous injection into the body, it quickly binds to protein, and the maximum absorption peak changes from 780nm in aqueous solution to 805nm. The ICG concentration in the blood is not affected by jaundice and hemolysis samples.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • BIOPHORE INDIA PHARMACEUTICALS PVT LTD

    United States United States
    Active
  • Nantong Jinghua Pharmaceutical Co Ltd

    United States United States
    Active
  • Wuhan Biocause Pharmaceutical Development Co., Ltd.

    China China
    Active

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