Indocyanine green

Identification

Summary

Indocyanine green is a diagnostic agent used for the determination of cardiac output, hepatic function and liver blood flow, and for ophthalmic angiography.

Brand Names
Ic-green
Generic Name
Indocyanine green acid form
Commonly known or available as Indocyanine green
DrugBank Accession Number
DB09374
Background

Indocyanine Green is a water soluble, tricarbocyanine dye with a peak spectral absorption at 800 nm. The chemical name for Indocyanine Green is 1 H-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. Indocyanine Green for Injection USP has a pH of approximately 6.5 when reconstituted. Each vial of Indocyanine Green for Injection USP contains 25 mg of Indocyanine Green as a sterile lyophilized powder with no more than 5% sodium iodide.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 753.99
Monoisotopic: 753.302656074
Chemical Formula
C43H49N2O6S2
Synonyms
Not Available
External IDs
  • Crysta-lyn 551522
  • NK 5078
  • NK-5078

Pharmacology

Indication

For Determining Cardiac Output, Hepatic Function and Liver Blood Flow For ophthalmic angiography

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Indocyanine Green for Injection USP undergoes no significant extrahepatic or enterohepatic circulation; simultaneous arterial and venous blood estimations have shown negligible renal, peripheral, lung or cerebro-spinal uptake of the dye. Indocyanine Green for Injection USP is taken up from the plasma almost exclusively by the hepatic parenchymal cells and is secreted entirely into the bile. After biliary obstruction, the dye appears in the hepatic lymph, independently of the bile, suggesting that the biliary mucosa is sufficiently intact to prevent diffusion of the dye, though allowing diffusion of bilirubin. These characteristics make Indocyanine Green for Injection USP a helpful index of hepatic function.

Absorption

It has a peak spectral absorption at about 800 nm.

Volume of distribution

ICG distribution into the mouse fetus can be enhanced when used concomitantly with OATP or P-glycoprotein inhibitors. The greater distribution within individual fetal tissues is likely related to ICG's greater transplacental transfer.

Protein binding

98%

Metabolism
Not Available
Route of elimination

The dye is excreted in bile in unconjugated form.

Half-life

ICG has a half-life of 150 to 180 seconds.

Clearance

Clearance of dyes which are removed from the circulation principally by the liver constitutes one of the best methods for evaluating hepatic function.

Adverse Effects
Adverseeffects
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Toxicity

Mouse LD50 60mg/kg ( intravenous ) Rat LD50 : 87mh/kg ( intravenous)

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AstemizoleIndocyanine green acid form may decrease the excretion rate of Astemizole which could result in a higher serum level.
AtazanavirAtazanavir may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
AtenololAtenolol may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
AtorvastatinAtorvastatin may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
AtropineAtropine may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
Belantamab mafodotinIndocyanine green acid form may decrease the excretion rate of Belantamab mafodotin which could result in a higher serum level.
BosentanBosentan may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
BudesonideBudesonide may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
CefaclorCefaclor may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
CelecoxibCelecoxib may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Indocyanine greenNot Available3599-32-4MOFVSTNWEDAEEK-UHFFFAOYSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IC-GreenKit25 mg/1IntravenousAkorn, Inc.2007-09-01Not applicableUS flag
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-15Not applicableUS flag
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-25Not applicableUS flag
IC-GreenPowder25 mgIntravenousAkorn Inc1994-12-31Not applicableCanada flag
Ic-greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2015-03-06Not applicableUS flag
Indocyanine Green for Injection KitKit; Powder, for solution25 mgIntravenousDiagnostic Green GmbHNot applicableNot applicableCanada flag
Indocyanine Green for Injection KitKit; Powder, for solution25 mgIntravenousDiagnostic Green GmbH2019-06-11Not applicableCanada flag
Indocyanine Green for Injection, USPPowder, for solution25 mgIntravenousDiagnostic Green GmbH2019-06-11Not applicableCanada flag
PINPOINT KitKit25 mg/1Interstitial; IntravenousNovadaq Technologies Inc2018-11-21Not applicableUS flag
Spy Agent GreenPowder, for solution25 mgInterstitial; IntravenousNovadaq Technologies Ulc2019-06-04Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2011-12-01Not applicableUS flag
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2015-12-01Not applicableUS flag
Indocyanine greenKit25 mg/1IntravenousNovadaq Technologies, Inc.1981-07-20Not applicableUS flag
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2012-07-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
IcgIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravenousKARL STORZ Endoscopy-America, Inc.2016-06-01Not applicableUS flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravenousOlympus America, Inc.2021-04-01Not applicableUS flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravenousRenew Pharmaceuticals Limited2008-01-01Not applicableUS flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (10 mL/1)KitIntravenousPulsion Medical Systems Se2008-01-012017-08-30US flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (10 mL/1)KitIntravenousHub Pharmaceuticals Llc2008-01-01Not applicableUS flag
PINPOINT Lymphatics KitIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravascular; IntravenousNovadaq Technologies Inc2018-11-21Not applicableUS flag
SPY Elite KitIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravascular; IntravenousNovadaq Technologies Inc2018-11-21Not applicableUS flag
SPY Lymphatics KitIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravascular; IntravenousNovadaq Technologies Inc2018-11-21Not applicableUS flag
SPY-MIS KitIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravascular; IntravenousNovadaq Technologies Inc2019-09-10Not applicableUS flag
SPY-PHI KitIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitIntravascular; IntravenousNovadaq Technologies Inc2019-09-10Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
C4V974V932
CAS number
28782-33-4
InChI Key
BDBMLMBYCXNVMC-UHFFFAOYSA-O
InChI
InChI=1S/C43H48N2O6S2/c1-42(2)38(44(28-14-16-30-52(46,47)48)36-26-24-32-18-10-12-20-34(32)40(36)42)22-8-6-5-7-9-23-39-43(3,4)41-35-21-13-11-19-33(35)25-27-37(41)45(39)29-15-17-31-53(49,50)51/h5-13,18-27H,14-17,28-31H2,1-4H3,(H-,46,47,48,49,50,51)/p+1
IUPAC Name
2-[(1E,3E,5E)-7-[(2Z)-1,1-dimethyl-3-(4-sulfobutyl)-1H,2H,3H-benzo[e]indol-2-ylidene]hepta-1,3,5-trien-1-yl]-1,1-dimethyl-3-(4-sulfobutyl)-1H-benzo[e]indol-3-ium
SMILES
CC1(C)\C(=C\C=C\C=C\C=C\C2=[N+](CCCCS(O)(=O)=O)C3=C(C4=CC=CC=C4C=C3)C2(C)C)N(CCCCS(O)(=O)=O)C2=C1C1=CC=CC=C1C=C2

References

General References
  1. Bishara A, Meir M, Portnoy E, Shmuel M, Eyal S: Near Infrared Imaging of Indocyanine Green Distribution in Pregnant Mice and Effects of Concomitant Medications. Mol Pharm. 2015 Sep 8;12(9):3351-7. doi: 10.1021/acs.molpharmaceut.5b00374. Epub 2015 Jul 25. [Article]
  2. DRUGS.COM [Link]
  3. ChemIDplus [Link]
  4. Pubchem [Link]
KEGG Drug
D01342
PubChem Compound
11967809
PubChem Substance
347827836
ChemSpider
18109
RxNav
2199577
ChEBI
31696
ChEMBL
CHEMBL1615807
ZINC
ZINC000008101127
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Indocyanine_green
FDA label
Download (3.75 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedDiagnosticCervical Cancers / Endometrial Cancer1
Not AvailableUnknown StatusNot AvailableDercum's Disease / Lipoedema / Lymphatic Disorders / Lymphedema / Vascular Anomalies / Vascular Malformations1
Not AvailableUnknown StatusNot AvailableLymph Node Mass / Lymphatic Vessel; Dilatation / Rheumatoid Arthritis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderIntravenous25 mg
Injection, powder, lyophilized, for solutionIntravenous25 mg/1
KitIntravenous
KitIntravenous25 mg/1
Kit; powder, for solutionIntravenous25 mg
Powder, for solutionIntravenous25 mg
KitInterstitial; Intravenous25 mg/1
Powder, for solutionInterstitial; Intravenous25 mg
Kit; powder, for solutionInterstitial; Intravenous25 mg
KitIntravascular; Intravenous
Injection, powder, for solutionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7881777No2011-02-012021-09-22US flag
US6915154No2005-07-052021-08-01US flag
US8647605No2014-02-112029-02-11US flag
US8185176No2012-05-222028-06-04US flag
US9421280No2016-08-232025-11-24US flag
US8406860No2013-03-262029-04-09US flag
US8892190No2014-11-182020-08-11US flag
US10631746No2020-04-282035-08-04US flag

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.82e-05 mg/mLALOGPS
logP2.26ALOGPS
logP6.05ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)-0.94ChemAxon
pKa (Strongest Basic)2.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.99 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity231.13 m3·mol-1ChemAxon
Polarizability87.2 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Cofactor
General Function
Receptor binding
Specific Function
Not Available
Gene Name
IDH1
Uniprot ID
O75874
Uniprot Name
Isocitrate dehydrogenase [NADP] cytoplasmic
Molecular Weight
46659.005 Da
References
  1. UniProt [Link]
  2. ChEMBL [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Takikawa H, Sano N, Akimoto K, Ogasawara T, Yamanaka M: Effects of colchicine and phenothiazine on biliary excretion of organic anions in rats. J Gastroenterol Hepatol. 1998 Apr;13(4):427-32. doi: 10.1111/j.1440-1746.1998.tb00658.x. [Article]
  2. Oude Elferink RP, Bakker CT, Roelofsen H, Middelkoop E, Ottenhoff R, Heijn M, Jansen PL: Accumulation of organic anion in intracellular vesicles of cultured rat hepatocytes is mediated by the canalicular multispecific organic anion transporter. Hepatology. 1993 Mar;17(3):434-44. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created on November 30, 2015 19:10 / Updated on October 21, 2021 04:40