INDOCYANINE GREEN ACID FORM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C43H48N2O6S2
Molecular Weight	752.981
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure of INDOCYANINE GREEN ACID FORM

Structure Search

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)C5=CC=C6C=CC=CC6=C15

InChI

InChIKey=BDBMLMBYCXNVMC-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/pro/indocyanine-green.html

ICG is a cyanine fluorescent dye which is used in medicine as an indicator substance (for photometric hepatic function diagnostics and fluorescence angiography) in cardiac, circulatory, hepatic and ophthalmic conditions. It is administered intravenously and, depending on liver performance, is eliminated from the body with a half life of approx. 3-4 minutes.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Age-related macular degeneration 20 Sources: http://www.amdbook.org/content/diagnostic-usefulness-indocyanine-green-angiography-icga-age-related-macular-degeneration-am	Diagnostic		Approved 8429	IC-GREEN INJECTABLE Approved Use Indocyanine Green is indicated for ophthalmic angiography. In ophtalmic angiography, Indocyanine Green is used for diagnosis of age-related macular degeneration, choroidal neovascularization, polypoidal choroidal vasculopathy, retinal angiomatous proliferation, choroidal melanoma, retinal damage and other pathological conditions Launch Date 1959
Surgery 2 Sources: https://www.drugs.com/pro/indocyanine-green.html	Diagnostic		Approved 8429	IC-GREEN INJECTABLE Approved Use Indocyanine Green is indicated for determining cardiac and heptic output during various types of surgeries. Launch Date 1959

C_max

Value	Dose	Co-administered	Analyte	Population
68095.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26629038	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		INDOCYANINE GREEN ACID FORM plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
121.6 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10883415	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: TRIAZOLAM	TRIAZOLAM	INDOCYANINE GREEN ACID FORM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
85 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8822042	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		INDOCYANINE GREEN ACID FORM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
503070.1 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26629038	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		INDOCYANINE GREEN ACID FORM plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.06 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10883415	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: TRIAZOLAM	TRIAZOLAM	INDOCYANINE GREEN ACID FORM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
3.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8822042	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		INDOCYANINE GREEN ACID FORM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
79.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26629038	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		INDOCYANINE GREEN ACID FORM plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% PATENT https://patents.google.com/patent/US20100303732			INDOCYANINE GREEN ACID FORM serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 46 n = 1 Health Status: unhealthy Age Group: 46 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	Other AEs: Anaphylactoid reaction... Other AEs: Anaphylactoid reaction Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
27 mg single, intravenous Dose: 27 mg Route: intravenous Route: single Dose: 27 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 48 n = 1 Health Status: unhealthy Age Group: 48 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	Other AEs: Anaphylactoid reaction... Other AEs: Anaphylactoid reaction Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2670244/	unhealthy, 63 n = 1 Health Status: unhealthy Condition: heart failure Age Group: 63 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2670244/	Other AEs: Anaphylactoid reaction... Other AEs: Anaphylactoid reaction Sources: https://pubmed.ncbi.nlm.nih.gov/2670244/
5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 66 n = 1 Health Status: unhealthy Age Group: 66 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	Other AEs: Anaphylactoid reaction... Other AEs: Anaphylactoid reaction Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
0.5 mg/kg single, intravenous Dose: 0.5 mg/kg Route: intravenous Route: single Dose: 0.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 70 n = 1 Health Status: unhealthy Age Group: 70 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	Other AEs: Anaphylactoid reaction... Other AEs: Anaphylactoid reaction Sources: https://pubmed.ncbi.nlm.nih.gov/671679/

AEs

AE	Dose	Population
Anaphylactoid reaction	5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 46 n = 1 Health Status: unhealthy Age Group: 46 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
Anaphylactoid reaction	27 mg single, intravenous Dose: 27 mg Route: intravenous Route: single Dose: 27 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 48 n = 1 Health Status: unhealthy Age Group: 48 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
Anaphylactoid reaction	5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2670244/	unhealthy, 63 n = 1 Health Status: unhealthy Condition: heart failure Age Group: 63 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2670244/
Anaphylactoid reaction	5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 66 n = 1 Health Status: unhealthy Age Group: 66 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/
Anaphylactoid reaction	0.5 mg/kg single, intravenous Dose: 0.5 mg/kg Route: intravenous Route: single Dose: 0.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/671679/	unhealthy, 70 n = 1 Health Status: unhealthy Age Group: 70 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/671679/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP2 4 OATP1B1 788 OATP1B3 706 OATP2B1 123 OAT3 642 BSEP 402	P-gp 1537 MRP2 205 BCRP 561 OATP1B1 406 OATP1B3 350

Drug as perpetrator

Target	Modality	Activity
OATP2 4	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0021925819342176 Page: 9627.0	yes [Ki 0.112 uM]
BSEP 403	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes
OAT3 644	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0021925818369291 Page: 13677.0	yes
OATP1B1 803	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes
OATP1B3 715	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes
OATP2B1 126	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes

Drug as victim

Target	Modality	Activity
BCRP 561	substrate 3367 Sources: https://pubs.acs.org/doi/abs/10.1021/mp300472y Page: 3599.0	no
MRP2 205	substrate 3367 Sources: https://pubs.acs.org/doi/abs/10.1021/mp300472y Page: 3599.0	yes
OATP1B1 406	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes
OATP1B3 350	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/bcpt.12671 Page: 176.0	yes
P-gp 1537	substrate 3367 Sources: https://pubs.acs.org/doi/abs/10.1021/mp300472y Page: 3599.0	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00I7LK
A2B Chem	AI48856
AA Blocks	AA00I724
AK Scientific	A711
AbovChem LLC	HY-D0711
Alfa Chemistry	ACM3599324
Ambeed	A201360
ApexBio Technology	B8315
AstaTech	C74855
BLD Pharm	BD134593
BOC Sciences	3599-32-4
Bide Pharmatech	BD134593
BindingDB	50420250	http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50420250
BlocksMatrix Scientific	99555
Chem-Impex International	22890
ChemIDplus	28782334	https://chem.nlm.nih.gov/chemidplus/id/0028782334
Compound Cloud	5282412
Compound Cloud	5282413
Hairui	HR135249
KeyOrganics	AS-11023
Lab Network	105
Lab Seeker	SC-09892
Life Chemicals	F9995-2721
MolPort	MolPort-003-928-011
MolPort	MolPort-019-996-360
MolPort	MolPort-042-620-237
Norris Pharm	NSZB-A233804
Sigma Aldrich	1340009
Sigma Aldrich	1340009\|USP
Sigma Aldrich	21980
Sigma Aldrich	21980\|SIAL
Sigma Aldrich	I2633\|SIGMA
StruChem	SC-09892
SureChEMBL	SCHEMBL15544158	https://www.surechembl.org/chemical/SCHEMBL15544158
Tetrahedron	TS01486
Toronto Research Chemicals	A794822
Toronto Research Chemicals	I697000
Wikidata	Q27275190
ZINC	ZINC000008101127	http://zinc15.docking.org/substances/ZINC000008101127
eMolecules	168890274
eMolecules	170921281
eMolecules	193068755
eMolecules	36364776
eMolecules	72977581
eNovation Chemicals	D279839

PubMed

Title	Date	PubMed
Survey of complications of indocyanine green angiography in Japan.	1994 Dec 15	7977601
Hypotensive shock as a complication of infracyanine green injection.	1998	9801048
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Multidrug resistance p-glycoprotein 2 is essential for the biliary excretion of indocyanine green.	2001 May	11302927
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.	2002 Jul	12065749
Cholestasis induced by model organic anions protects from acetaminophen hepatotoxicity in male CD-1 mice.	2006 Jan 25	16140478
Retinal pigmented epithelial cells cytotoxicity and apoptosis through activation of the mitochondrial intrinsic pathway: role of indocyanine green, brilliant blue and implications for chromovitrectomy.	2013	23675521
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013 Dec	24014644

Patents

Sample Use Guides

In Vivo Use Guide

The usual doses of Indocyanine Green for Injection USP for dilution curves are as follows: adults - 5.0 mg, children - 2.5 mg, infants - 1.25 mg. These doses of the dye are usually injected in 1 mL volume. An average of five dilution curves are recommended in the performance of a diagnostic cardiac catheterization. The total dose of dye injected should be kept below 2 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

INDOCYANINE GREEN ACID FORM

Common Name

English

NK-5078

Code

English

CRYSTA-LYN 551522

Brand Name

English

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

Common Name

English

NK 5078

Code

English

Code System Code Type Description

EPA CompTox

DTXSID9048279