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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 of GADODIAMIDE

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
Molecular Formula Gd
Molecular Weight 157.25
Charge 3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H26N5O8
Molecular Weight 416.4063
Charge -3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: A 2015 study found trace amounts of Gadolinium deposited in the brain tissue of patients that had received Gadodiamide.

Originator

Salutar
2
Curator's Comment: Gadodiamide was developed by Salutar (Sunnyvale, Calif).

Approval Year

1993
136
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Neurotoxic potential of gadodiamide after injection into the lateral cerebral ventricle of rats.
1998 Sep
Gadolinium arteriography complicated by acute pancreatitis and acute renal failure.
2001 Mar
Gadodiamide-associated nephrogenic systemic fibrosis.
2007 Jun
Gadolinium-associated nephrogenic systemic fibrosis: double dose, not single dose.
2007 Jun
Case-control study of gadodiamide-related nephrogenic systemic fibrosis.
2007 Nov
Comparison of the usefulness of gadodiamide and iodine mixture versus iodinated contrast alone for prevention of contrast-induced nephropathy in patients with chronic kidney disease undergoing coronary angiography.
2007 Oct 1
Nephrogenic systemic fibrosis: possible association with a predisposing infection.
2008 Apr
Gadolinium-based contrast exposure, nephrogenic systemic fibrosis, and gadolinium detection in tissue.
2008 Apr
A preclinical study to investigate the development of nephrogenic systemic fibrosis: a possible role for gadolinium-based contrast media.
2008 Jan
Clinical manifestation of gadodiamide-related nephrogenic systemic fibrosis.
2008 Mar
Gadolinium-based contrast agents and their potential role in the pathogenesis of nephrogenic systemic fibrosis: the role of excess ligand.
2008 May
An epidemic outbreak of nephrogenic systemic fibrosis in a Danish hospital.
2008 May
Regulation of collagen turnover in human skin fibroblasts exposed to a gadolinium-based contrast agent.
2009 Aug
Induction of the expression of profibrotic cytokines and growth factors in normal human peripheral blood monocytes by gadolinium contrast agents.
2009 May
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
The role of residual gadolinium in the induction of nephrogenic systemic fibrosis-like skin lesions in rats.
2011 Jan
Semi-quantification of endolymphatic size on MR imaging after intravenous injection of single-dose gadodiamide: comparison between two types of processing strategies.
2013 Dec 25
The gadolinium-based contrast agent Omniscan® promotes in vitro fibroblast survival through in situ precipitation.
2015 Jul
Intrathecal gadodiamide for identifying subarachnoid and ventricular neurocysticercosis.
2015 Jul
IV Administered Gadodiamide Enters the Lumen of the Prostatic Glands: X-Ray Fluorescence Microscopy Examination of a Mouse Model.
2015 Sep
T1 Signal-Intensity Increase in the Dentate Nucleus after Multiple Exposures to Gadodiamide: Intraindividual Comparison between 2 Commonly Used Sequences.
2016 Aug
Cochlear Lymph Fluid Signal Increase in Patients with Otosclerosis after Intravenous Administration of Gadodiamide.
2016 Jul 11
Investigation of the ototoxicity of gadoteridol (ProHance) and gadodiamide (Omniscan) in mice.
2016 Nov
Signal intensity change on unenhanced T1-weighted images in dentate nucleus following gadobenate dimeglumine in patients with and without previous multiple administrations of gadodiamide.
2016 Nov
Patents

Patents

20060069098
2

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:01 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:01 GMT 2023
Record UNII
84F6U3J2R6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GADODIAMIDE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
NCI_THESAURUS C62358
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
WHO-VATC QV08CA03
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
NDF-RT N0000180184
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
NDF-RT N0000175862
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
WHO-ATC V08CA03
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
EU-Orphan Drug EU/3/08/583
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65795
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
DAILYMED
84F6U3J2R6
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
EVMPD
SUB126939
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
WIKIPEDIA
GADODIAMIDE
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
MESH
C064925
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
FDA UNII
84F6U3J2R6
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1287507
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
USAN
CC-17
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
RXCUI
41144
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY RxNorm
CAS
131410-48-5
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
DRUG CENTRAL
4494
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
SMS_ID
100000085190
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
MERCK INDEX
m5624
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY Merck Index
PUBCHEM
153921
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
LACTMED
Gadodiamide
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
CHEBI
31642
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200346
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
HSDB
7547
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID201019701
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
EVMPD
SUB07862MIG
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
INN
6636
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
DRUG BANK
DB00225
Created by admin on Fri Dec 15 15:54:01 GMT 2023 , Edited by admin on Fri Dec 15 15:54:01 GMT 2023
PRIMARY
Related Record Type Details
Structure of GADODIAMIDE HYDRATE
SOLVATE->ANHYDROUS
Structure of GADODIAMIDE
BASIS OF STRENGTH->SUBSTANCE
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of GADODIAMIDE HYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of GADOLINIUM SODIUM DIETHYLENETRIAMINE PENTAACETIC ACID
IMPURITY -> PARENT
Related Record Type Details
Structure of GADODIAMIDE
ACTIVE MOIETY
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