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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22I3N3O8
Molecular Weight 789.096
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METRIZAMIDE

SMILES

CN(C(C)=O)C1=C(I)C(C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=DTZMSDADRKLCQE-RFMXWLSYSA-N
InChI=1S/C18H22I3N3O8/c1-6(27)22-14-11(19)10(12(20)15(13(14)21)24(3)7(2)28)18(32)23-8(4-25)16(30)17(31)9(29)5-26/h4,8-9,16-17,26,29-31H,5H2,1-3H3,(H,22,27)(H,23,32)/t8-,9+,16+,17+/m0/s1

HIDE SMILES / InChI

Description

Metrizamide is a glucosamine derivative of metrazoic acid, used as a contrast medium for myelography. Metrizamide is no longer marketed in the US.

CNS Activity

CNS Non-penetrant
1040
Curator's Comment: The blood-brain barrier of rats is impermeable to metrizamide.

Originator

Almen, T.|Nyegaard
1
Curator's Comment: In 1968, Torsten Almen, working in conjunction with Nyegaard, produced the first clinically acceptable non ionic contrast medium, Amipaque (metrizamide, Winthrop).

Approval Year

1978
88
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8583
AMIPAQUE

Approved Use

Unknown

Launch Date

1978
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1151624/
1700 mg single, intrathecal
dose: 1700 mg
route of administration: Intrathecal
experiment type: SINGLE
co-administered:
METRIZAMIDE serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
208 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1151624/
1700 mg single, intrathecal
dose: 1700 mg
route of administration: Intrathecal
experiment type: SINGLE
co-administered:
METRIZAMIDE serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.75 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1151624/
1700 mg single, intrathecal
dose: 1700 mg
route of administration: Intrathecal
experiment type: SINGLE
co-administered:
METRIZAMIDE serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.0351966873706 g/kg single, intravenous
Highest studied dose
Dose: 1.0351966873706 g/kg
Route: intravenous
Route: single
Dose: 1.0351966873706 g/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/433646
unhealthy, 32 - 71 years
Health Status: unhealthy
Age Group: 32 - 71 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/433646
Sources:
https://pubmed.ncbi.nlm.nih.gov/433646
Sourcing

Sourcing

Vendor/AggregatorIDURL
MolPort
MolPort-046-857-011
TimTec
ST51006711
ZINC
ZINC000150485244
http://zinc15.docking.org/substances/ZINC000150485244
PubMed

PubMed

TitleDatePubMed
Malignant hyperthermia-like syndrome associated with metrizamide myelography.
1989-06
A possible mechanism for the neural adverse reactions caused by metrizamide.
1989
Risk of seizures after myelography: comparison of iohexol and metrizamide.
1988-09
Absence status epilepticus resulting from metrizamide and omnipaque myelography.
1988-01
Metrizamide--a potential in vivo inhibitor of glucose metabolism.
1983-04
Proteinuria following nephroangiography. IV. Comparison in dogs between ionic and non-ionic contrast media.
1979
ECG changes and arrhythmias induced by ionic and non-ionic contrast media during coronary arteriography in dogs.
1978-05-01
Metrizamide-phenothiazine interaction. Report of a case with seizures following myelography.
1975-03
Patents

Patents

JP2002539853A
1
JP2002543940A
2
JP2011511651A
2

Sample Use Guides

In Vivo Use Guide
300 mgI/ml as one injection
Route of Administration: Intra-arterial
In Vitro Use Guide
Cultured endothelial cells derived from human umbilical cord veins were labeled with Na2 (51Cr)O4 and exposed to pure isoiodinated contrast media or control solutions for 10 minutes to simulate the effects of intravenous injections of contrast media on the human endothelium. Metrizamide was used at 300 mgI/ml.
Name Type Language
AMIPAQUE
Preferred Name English
METRIZAMIDE
INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
WIN 39103
Code English
D-GLUCOSE, 2-((3-(ACETYLAMINO)-5-(ACETYLMETHYLAMINO)-2,4,6-TRIIODOBENZOYL)AMINO)-2-DEOXY-
Systematic Name English
WIN-39103
Code English
3-ACETAMIDO-2,4,6-TRIIODO-5-(N-METHYLACETAMIDO)-N-((2R,3R,4S,5R)-3,4,5,6-TETRAHYDROXY-1-OXOHEXAN-2-YL)BENZAMIDE
Systematic Name English
2-(3-ACETAMIDO-2,4,6-TRIIODO-5-(N-METHYLACETAMIDO)BENZAMIDO)-2-DEOXY-D-GLUCOPYRANOSE
Systematic Name English
3-ACETAMIDO-2,4,6-TRIIODO-5-(N-METHYLACETAMIDO)-N-((3R,4R,5S,6R)-2,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3-YL)BENZAMIDE
Systematic Name English
METRIZAMIDE [MART.]
Common Name English
METRIZAMIDE [VANDF]
Common Name English
TELEBRIX 300
Brand Name English
metrizamide [INN]
Common Name English
METRIZAMIDE [ORANGE BOOK]
Common Name English
2-(3-ACETAMIDO-2,4,6-TRIIODO-5-(N-METHYLACETAMIDO)BENZAMIDO)-2-DEOXY-D-GLUCOSE
Systematic Name English
METRIZAMIDE [MI]
Common Name English
METRIZAMIDE [JAN]
Common Name English
Metrizamide [WHO-DD]
Common Name English
METRIZAMIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C390
Created by admin on Mon Mar 31 18:23:53 GMT 2025 , Edited by admin on Mon Mar 31 18:23:53 GMT 2025
WHO-VATC QV08AB01
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WHO-ATC V08AB01
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Code System Code Type Description
INN
3116
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PRIMARY
MERCK INDEX
m7504
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PRIMARY Merck Index
CAS
55134-11-7
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ALTERNATIVE
ChEMBL
CHEMBL1200889
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PRIMARY
EPA CompTox
DTXSID1023310
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PRIMARY
FDA UNII
RHH3W8F1CO
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PRIMARY
DRUG CENTRAL
1788
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PRIMARY
DRUG BANK
DB01578
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PRIMARY
MESH
D008793
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PRIMARY
EVMPD
SUB08921MIG
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PRIMARY
NCI_THESAURUS
C66139
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PRIMARY
SMS_ID
100000080928
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PRIMARY
PUBCHEM
20056604
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PRIMARY
RXCUI
6920
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PRIMARY RxNorm
CAS
31112-62-6
Created by admin on Mon Mar 31 18:23:53 GMT 2025 , Edited by admin on Mon Mar 31 18:23:53 GMT 2025
PRIMARY
WIKIPEDIA
METRIZAMIDE
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PRIMARY
ECHA (EC/EINECS)
250-475-5
Created by admin on Mon Mar 31 18:23:53 GMT 2025 , Edited by admin on Mon Mar 31 18:23:53 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of METRIZAMIDE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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