GADODIAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H26N5O8.Gd
Molecular Weight	573.66
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Gd+3].CNC(=O)CN(CCN(CCN(CC([O-])=O)CC(=O)NC)CC([O-])=O)CC([O-])=O

InChI

InChIKey=HZHFFEYYPYZMNU-UHFFFAOYSA-K

InChI=1S/C16H29N5O8.Gd/c1-17-12(22)7-20(10-15(26)27)5-3-19(9-14(24)25)4-6-21(11-16(28)29)8-13(23)18-2;/h3-11H2,1-2H3,(H,17,22)(H,18,23)(H,24,25)(H,26,27)(H,28,29);/q;+3/p-3

HIDE SMILES / InChI

Description
Sources: http://www3.gehealthcare.com.au/en-au/products/categories/contrast_media

Gadodiamide is a nonionic, low-osmolar gadolinium-based contrast agent for diagnostic contrast-enhanced magnetic resonance imaging (MRI).

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Contrast agent for MRI 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022066s007,020123s043lbl.pdf	Diagnostic		Approved 8429	OMNISCAN Approved Use Diagnostic magnetic resonance imaging (MRI) indicated for intravenous use to visualize lesions with abnormal vascularity in the brain, spine, and associated tissues; facilitate the visualization of lesions with abnormal vascularity within the thoracic, abdominal, pelvic cavities, and the retroperitoneal space. Launch Date 1993

T_1/2

Value	Dose	Co-administered	Analyte	Population
77.8 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022066lbl.pdf	0.1 mmol/kg single, intravenous dose: 0.1 mmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:		GADODIAMIDE unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022066lbl.pdf	0.1 mmol/kg single, intravenous dose: 0.1 mmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:		GADODIAMIDE unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/201277Orig1s000PharmR.pdf#page=53 Page: 53.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:37333	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:37333
ChemicalBook	CB1501382	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1501382
MolPort	MolPort-046-417-370	https://www.molport.com/shop/molecule-link/MolPort-046-417-370
eMolecules	10135332	https://www.emolecules.com/cgi-bin/more?vid=10135332

PubMed

Title	Date	PubMed
Neurotoxic potential of gadodiamide after injection into the lateral cerebral ventricle of rats.	1998 Sep	9763378
Gadolinium arteriography complicated by acute pancreatitis and acute renal failure.	2001 Mar	11287523
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.	2008 Apr	18356456
A preclinical study to investigate the development of nephrogenic systemic fibrosis: a possible role for gadolinium-based contrast media.	2008 Jan	18097279
Clinical manifestation of gadodiamide-related nephrogenic systemic fibrosis.	2008 Mar	18397714
Gadolinium-based contrast agents and their potential role in the pathogenesis of nephrogenic systemic fibrosis: the role of excess ligand.	2008 May	18425843
An epidemic outbreak of nephrogenic systemic fibrosis in a Danish hospital.	2008 May	18328659
Regulation of collagen turnover in human skin fibroblasts exposed to a gadolinium-based contrast agent.	2009 Aug	19561517
Induction of the expression of profibrotic cytokines and growth factors in normal human peripheral blood monocytes by gadolinium contrast agents.	2009 May	19404939
NFκB activation and stimulation of chemokine production in normal human macrophages by the gadolinium-based magnetic resonance contrast agent Omniscan: possible role in the pathogenesis of nephrogenic systemic fibrosis.	2010 Nov	20959327
The role of residual gadolinium in the induction of nephrogenic systemic fibrosis-like skin lesions in rats.	2011 Jan	20938346
IV Administered Gadodiamide Enters the Lumen of the Prostatic Glands: X-Ray Fluorescence Microscopy Examination of a Mouse Model.	2015 Sep	26295667
T1 Signal-Intensity Increase in the Dentate Nucleus after Multiple Exposures to Gadodiamide: Intraindividual Comparison between 2 Commonly Used Sequences.	2016 Aug	27032972
Investigation of the ototoxicity of gadoteridol (ProHance) and gadodiamide (Omniscan) in mice.	2016 Nov	27315460

Patents

Sample Use Guides

In Vivo Use Guide

0.2 mL/kg (CNS), 0.1 mL/kg (kidney), 0.2 mL/kg (Intrathoracic, intra-abdominal, and pelvic cavities)

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

GADODIAMIDE

Official Name

English

GADODIAMIDE [USP-RS]

Common Name

English

GADODIAMIDE ANHYDROUS

Common Name

English

GADODIAMIDE [USP MONOGRAPH]

Common Name

English

GDDTPA-BMA

Code

English

S-041

Code

English

OMNISCAN

Brand Name

English

GADODIAMIDE [HSDB]

Common Name

English

GADODIAMIDE [VANDF]

Common Name

English

GADODIAMIDE [ORANGE BOOK]

Common Name

English

(5,8-BIS(CARBOXYMETHYL)-11-(2-(METHYLAMINO)-2-OXOETHYL)-3-OXO-2,5,8,11-TETRAAZATRIDECAN-13-OATO(3-))GADOLINIUM

Common Name

English

GADODIAMIDE [USAN]

Common Name

English

gadodiamide [INN]

Common Name

English

GADODIAMIDE [MI]

Common Name

English

GADODIAMIDE [MART.]

Common Name

English

[N,N-Bis[2-[(carboxymethyl)[(methylcarbamoyl)methyl]amino]ethyl]glycinato(3-)]gadolinium

Common Name

English

Gadodiamide [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

268408