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
Weight
Average: 752.99
Monoisotopic: 752.295379622
Chemical Formula
C43H48N2O6S2
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

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
AstemizoleAstemizole may decrease the excretion rate of Indocyanine green acid form 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.
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Indocyanine greenIX6J1063HV3599-32-4MOFVSTNWEDAEEK-UHFFFAOYSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-25Not applicableUS flag
IC-GreenPowder25 mg / vialIntravenousAkorn Inc1994-12-312021-03-01Canada flag
Ic-greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2015-03-06Not applicableUS flag
IC-GreenKit25 mg/1IntravenousAkorn2007-09-01Not applicableUS flag
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-15Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
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
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
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 (10 mL/1)KitIntravenousPulsion Medical Systems Se2008-01-012017-08-30US flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (10 mL/1)Injection, powder, lyophilized, for solution; KitIntravenousHub Pharmaceuticals Llc2008-01-01Not applicableUS flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (1 mL/1mL)Injection, powder, lyophilized, for solution; KitIntravenousOlympus America, Inc.2021-04-01Not applicableUS flag
Indocyanine GreenIndocyanine green (25 mg/1) + Water (1 mL/1mL)Injection, powder, lyophilized, for solution; KitIntravenousRenew Pharmaceuticals Limited2008-01-01Not 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-N
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)
IUPAC Name
2-{7-[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-sulfonatobutyl)-1H-benzo[e]indol-3-ium
SMILES
CC1(C)C(=CC=CC=CC=CC2=[N+](CCCCS([O-])(=O)=O)C3=CC=C4C=CC=CC4=C3C2(C)C)N(CCCCS(O)(=O)=O)C2=CC=C3C=CC=CC3=C12

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
19800615
BindingDB
50420250
RxNav
2199577
ChEBI
31696
ChEMBL
CHEMBL1201304
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
4RecruitingPreventionGastric Ulcer / Obesity, Morbid1
4WithdrawnTreatmentCubital Tunnel Syndrome1
Not AvailableCompletedDiagnosticCervical Cancer / 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 / vial
Injection, powder, lyophilized, for solutionIntravenous25 mg/1
Injection, powder, lyophilized, for solution; kitIntravenous
KitIntravenous
KitIntravenous25 mg/1
Kit; powder, for solutionIntravenous25 mg / vial
Powder, for solutionIntravenous25 mg / vial
KitInterstitial; Intravenous25 mg/1
KitIntravascular; Intravenous
Powder, for solutionInterstitial; Intravenous25 mg / vial
Kit; powder, for solutionInterstitial; Intravenous25 mg / vial
KitIntradermal; Intravascular; Intravenous
Injection, powder, for solutionIntravenous5 mg/ml
PowderIntravenous25 mg/1vial
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
US11712320No2019-07-142039-07-14US flag

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP6.05Chemaxon
pKa (Strongest Acidic)-0.94Chemaxon
pKa (Strongest Basic)4.85Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area117.82 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity230 m3·mol-1Chemaxon
Polarizability86.55 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
Chromatographic Properties
Collision Cross Sections (CCS)
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 at November 30, 2015 19:10 / Updated at February 27, 2024 23:09