Identification

Name
Indocyanine green acid form
Commonly known or available as Indocyanine green
Accession Number
DB09374
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
Crysta-lyn 551522 / NK 5078 / NK-5078
Product Ingredients
IngredientUNIICASInChI Key
Indocyanine greenIX6J1063HV3599-32-4MOFVSTNWEDAEEK-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IC-GreenKit25 mg/1IntravenousAkorn2007-09-01Not applicableUs
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-25Not applicableUs
Ic-greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2015-03-06Not applicableUs
IC-GreenPowder25 mgIntravenousAkorn1994-12-31Not applicableCanada
IC-GreenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2013-09-15Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2015-12-01Not applicableUs
Indocyanine greenKit25 mg/1Novadaq Technologies, Inc.1981-07-20Not applicableUs
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2012-07-01Not applicableUs
Indocyanine GreenKit25 mg/1Diagnostic Green GmbH2008-01-01Not applicableUs
Indocyanine greenInjection, powder, lyophilized, for solution25 mg/1IntravenousNovadaq Technologies, Inc.2011-12-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
IcgIndocyanine green (25 mg/1) + Water (1 mL/1mL)KitKARL STORZ Endoscopy-America, Inc.2016-06-01Not applicableUs
Indocyanine GreenIndocyanine green (25 mg/1) + Water (10 mL/1)KitHub Pharmaceuticals Llc2008-01-01Not applicableUs
Indocyanine GreenIndocyanine green (25 mg/1) + Water (10 mL/1)KitPulsion Medical Systems Se2008-01-012017-08-30Us
Categories
UNII
C4V974V932
CAS number
28782-33-4
Weight
Average: 753.99
Monoisotopic: 753.302656074
Chemical Formula
C43H49N2O6S2
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

Pharmacology

Indication

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

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.

Toxicity

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

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
BudesonideIndocyanine green acid form may decrease the excretion rate of Budesonide which could result in a higher serum level.
ChlorpromazineChlorpromazine may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
ClotrimazoleClotrimazole may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
DaunorubicinDaunorubicin may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
DexamethasoneDexamethasone may increase the excretion rate of Indocyanine green acid form which could result in a lower serum level and potentially a reduction in efficacy.
DiclofenacIndocyanine green acid form may decrease the excretion rate of Diclofenac which could result in a higher serum level.
DipyridamoleIndocyanine green acid form may decrease the excretion rate of Dipyridamole which could result in a higher serum level.
ErythromycinIndocyanine green acid form may decrease the excretion rate of Erythromycin which could result in a higher serum level.
EthinylestradiolEthinyl Estradiol may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
FelodipineIndocyanine green acid form may decrease the excretion rate of Felodipine which could result in a higher serum level.
Food Interactions
Not Available

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. [PubMed:26149724]
  2. DRUGS.COM [Link]
  3. Wikipedia [Link]
  4. ChemIDplus [Link]
  5. Pubchem [Link]
External Links
KEGG Drug
D01342
PubChem Compound
11967809
PubChem Substance
347827836
ChemSpider
18109
ChEBI
31696
ChEMBL
CHEMBL1615807
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Indocyanine_green
AHFS Codes
  • 36:18.00 — Cardiac Function
  • 36:44.00 — Liver Function
FDA label
Download (3.75 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceDetermination of the Occlusion Pressure in Lymphatic Vessels1
0CompletedDiagnosticCancer of the Breast / Cancer, Breast / Malignant Melanoma / Melanoma1
0CompletedDiagnosticDuctal Carcinoma / Invasive Ductal Carcinoma / Invasive Lobular Carcinoma1
0CompletedDiagnosticHepatocellular,Carcinoma1
0CompletedDiagnosticSolitary Pulmonary Nodules1
0Not Yet RecruitingBasic ScienceLymphatic Function1
0Unknown StatusBasic ScienceMicrocirculation / Reconstructive Surgery1
1Active Not RecruitingDiagnosticLung Cancers1
1CompletedBasic ScienceCholestasis / Primary Biliary Cirrhosis (PBC) / Primary Sclerosing Cholangitis (PSC)1
1CompletedDiagnosticAcute Calculous Cholecystitis / Acute Cholangitis1
1CompletedDiagnosticAtherosclerosis / Carotid Stenosis / Plaque, Atherosclerotic1
1CompletedDiagnosticEsophageal Cancers1
1CompletedDiagnosticMelanoma1
1CompletedDiagnosticNeoplasms1
1CompletedDiagnosticNeoplasms, Malignant1
1CompletedDiagnosticNeoplasms / Tumors, Solid1
1CompletedDiagnosticStage IIA Prostate Cancer / Stage IIB Prostate Cancer1
1CompletedOtherNeoplasms, Lung1
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentEsophageal Cancers / Lung Cancers1
1CompletedTreatmentMelanoma (Skin) / Metastatic Cancers1
1CompletedTreatmentRenal Cell Cancer, Recurrent / Stage I Renal Cell Cancer / Stage II Renal Cell Cancer1
1Enrolling by InvitationTreatmentPrimary Brain Tumors / Recurrent Brain Tumors1
1Not Yet RecruitingDiagnosticCervical Intraepithelial Neoplasia (CIN)1
1Not Yet RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Thoracic Surgery1
1RecruitingBasic ScienceLymphedema of the extremities / Rheumatoid Arthritis1
1RecruitingBasic ScienceLymphedema of the extremities1
1RecruitingDiagnosticCancers of the Head and Neck / Head and Neck Carcinoma1
1RecruitingDiagnosticCervical Cancers2
1RecruitingDiagnosticChronic Lung Diseases / Neoplasms / Neoplasms by Site / Neoplasms, Lung / Thoracic Neoplasms1
1RecruitingDiagnosticProstate Cancer1
1RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1, 2CompletedDevice FeasibilityPulmonary Nodule, Multiple / Pulmonary Nodule, Solitary1
1, 2CompletedDiagnosticCancer, Breast1
1, 2CompletedTreatmentLung Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2Enrolling by InvitationOtherGeneral Surgery / Rectal Carcinoma / Urethra Injury1
1, 2Enrolling by InvitationTreatmentCancer of Rectum / Lymph Node Disease1
1, 2RecruitingNot AvailableAcute Anoxic Encephalopathy / Intracerebral Hemorrhage / Stroke, Ischemic / Subarachnoid Hemorrhage / Traumatic Brain Injury (TBI)1
1, 2RecruitingDiagnosticSuspected Central Nervous System Tumors1
1, 2RecruitingOtherChylothorax / Esophageal Cancers / Thoracic Duct Intra-Operative Injury1
1, 2RecruitingOtherSentinel Lymph Node1
2CompletedDiagnosticCancer, Breast2
2CompletedDiagnosticColorectal Cancers1
2CompletedDiagnosticColorectal Cancers / Peritoneal Carcinomatosis1
2CompletedDiagnosticEndometriosis Outside Pelvis / Pelvic Endometriosis1
2CompletedDiagnosticPeripheral Arterial Disease (PAD)1
2CompletedTreatmentPeriodontitis1
2Enrolling by InvitationTreatmentIndocyanine Green / Stomach Neoplasms1
2RecruitingNot AvailableCancer, Breast1
2RecruitingDiagnosticTransplantation, Kidney1
2RecruitingTreatmentCancer, Breast2
2TerminatedSupportive CareLymphedema of the extremities / Recurrent Breast Cancer / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer1
2Unknown StatusDiagnosticCancer, Breast2
2Unknown StatusDiagnosticHead and Neck Carcinoma1
2, 3RecruitingDiagnosticPediatric Patients With Solid Tumors1
2, 3TerminatedPreventionFractures, Comminuted / Necrosis / Surgical Wound Dehiscence1
3CompletedDiagnosticNeoplasms, Breast1
3RecruitingDiagnosticAnus Cancer / Cancer of the Ovary / Carcinoma, Breast / Cervix Cancer / Endometrium Cancer / Head and Neck Carcinoma / Melanoma (Skin) / Rectum Cancer / Squamous Cell Carcinoma, Skin / Vulva Cancer1
3WithdrawnDiagnosticProstatic Neoplasms1
4Not Yet RecruitingDiagnosticLymphedema of the extremities1
4RecruitingDiagnosticNeoplasms, Breast1
4RecruitingTreatmentDeep Endometriosis / Recto Vaginal Node1
4WithdrawnOtherSclerosis, Progressive Systemic1
Not AvailableActive Not RecruitingTreatmentBreastcancer1
Not AvailableCompletedNot AvailableMetastatic Colorectal Cancers1
Not AvailableCompletedDiagnosticBiliary Colic / Gallbladder disorders / Gallstone formation1
Not AvailableCompletedDiagnosticColorectal Polyps / Distal Colonic Lesions / High Risk Polyposis Syndrome1
Not AvailableCompletedDiagnosticEndometrial Cancers1
Not AvailableCompletedDiagnosticGallbladder Inflammation1
Not AvailableCompletedDiagnosticMelanoma / Sentinel Node1
Not AvailableCompletedDiagnosticSkull Base Neoplasm / Skull Base Neoplasms1
Not AvailableCompletedOtherHead and Neck Carcinoma1
Not AvailableCompletedPreventionGallbladder Inflammation / Gallstone formation1
Not AvailableCompletedTreatmentCancer, Breast / Ductal Carcinoma in Situ - Category / Prophylactic Mastectomy1
Not AvailableCompletedTreatmentCancer, Breast / Sentinel Lymph Node1
Not AvailableCompletedTreatmentColic of Gallbladder Without Mention of Cholecystitis / Gallbladder Inflammation / Gallstone formation / Pancreatitis Biliary1
Not AvailableCompletedTreatmentIdiopathic Epiretinal Membrane, Cataract1
Not AvailableCompletedTreatmentMinor burns1
Not AvailableEnrolling by InvitationNot AvailableDercum Disease / Lipoedema / Lymphatic Disorders / Lymphedema of the extremities / Vascular Anomalies / Vascular Malformations1
Not AvailableEnrolling by InvitationTreatmentCancer, Breast / Sentinel Lymph Node1
Not AvailableNot Yet RecruitingTreatmentDiabetic Extremity Lower Ulcers1
Not AvailableRecruitingNot AvailableAbove Knee Amputation / Below Knee Amputation / Lower Extremity Amputation / Wound Healing1
Not AvailableRecruitingNot AvailableBladder Cancers / Malignant Neoplasm of Stomach1
Not AvailableRecruitingNot AvailableLymph Node Mass / Lymphatic Vessel; Dilatation / Rheumatoid Arthritis1
Not AvailableRecruitingBasic ScienceLymphedema, Secondary1
Not AvailableRecruitingDiagnosticEndometrial Cancers / Indocyanine Green / Sentinel Lymph Node1
Not AvailableRecruitingDiagnosticLeak, Anastomotic1
Not AvailableRecruitingDiagnosticLymph Node Metastasis / Melanoma1
Not AvailableRecruitingDiagnosticNeoplasms, Head and Neck1
Not AvailableRecruitingDiagnosticStage I Breast Carcinoma / Stage II Breast Cancer1
Not AvailableRecruitingPreventionCancer, Breast / Lymphadenectomy1
Not AvailableSuspendedDiagnosticGastric (Stomach) Cancer / Gastrointestinal Diseases / Gastrointestinal Stromal Tumors / Gastrointestinal Stromal Tumors (GISTs) / Malignant Neoplasm of Stomach1
Not AvailableTerminatedDiagnosticStage I Endometrial Carcinoma / Stage II Endometrial Carcinoma / Stage III Endometrial Carcinoma / Stage IV Endometrial Carcinoma1
Not AvailableUnknown StatusNot AvailableCarpal Tunnel Syndrome (CTS)1
Not AvailableUnknown StatusDiagnosticRecurrent Melanoma / Stage IA Melanoma / Stage IB Melanoma / Stage IIA Melanoma / Stage IIB Melanoma / Stage IIC Melanoma / Stage IIIA Melanoma / Stage IIIB Melanoma / Stage IIIc Melanoma / Stage IV Melanoma1
Not AvailableWithdrawnDiagnosticLung Cancers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitIntravenous25 mg/1
PowderIntravenous25 mg
Kit
Injection, powder, lyophilized, for solutionIntravenous25 mg/1
Kit25 mg/1
Prices
Not Available
Patents
Not Available

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

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Yes
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]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Catalytic activity
General Function
Glutaminase activity
Specific Function
Catalyzes the first reaction in the primary pathway for the renal catabolism of glutamine. Plays a role in maintaining acid-base homeostasis. Regulates the levels of the neurotransmitter glutamate ...
Gene Name
GLS
Uniprot ID
O94925
Uniprot Name
Glutaminase kidney isoform, mitochondrial
Molecular Weight
73460.56 Da
References
  1. UniProt [Link]
  2. ChEMBL [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Transporter
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. UniProt [Link]
  2. ChEMBL [Link]
Kind
Protein
Organism
Human
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. [PubMed:24014644]

Drug created on November 30, 2015 12:10 / Updated on September 18, 2018 23:02