U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H20I6N4O8.2C7H17NO5
Molecular Weight 1644.2916
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOCARMATE MEGLUMINE

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(NC(=O)CCCCC(=O)NC2=C(I)C(C(=O)NC)=C(I)C(C(O)=O)=C2I)=C(I)C(C(O)=O)=C1I

InChI

InChIKey=HOBKVSAGFBYKRQ-VRWDCWMNSA-N
InChI=1S/C24H20I6N4O8.2C7H17NO5/c1-31-21(37)9-13(25)11(23(39)40)17(29)19(15(9)27)33-7(35)5-3-4-6-8(36)34-20-16(28)10(22(38)32-2)14(26)12(18(20)30)24(41)42;2*1-8-2-4(10)6(12)7(13)5(11)3-9/h3-6H2,1-2H3,(H,31,37)(H,32,38)(H,33,35)(H,34,36)(H,39,40)(H,41,42);2*4-13H,2-3H2,1H3/t;2*4-,5+,6+,7+/m.00/s1

HIDE SMILES / InChI

Molecular Formula C24H20I6N4O8
Molecular Weight 1253.8644
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H17NO5
Molecular Weight 195.2136
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Iocarmic acid is a molecule used in seventies as a contrast media for myelography. Iocarmate meglumine (Dimer-X), a water-soluble salt of iocarmic acid was reported to be safe and best tolerated by central nervous system compared to metrizamide in a double-blind test in patients with symptoms of lumbar and sacral root involvement. In the experimental and clinical studies of Dimer-X used for ventriculography the apparent superiority of Dimer-X over Conray 60 and Angiografin as far as side effects were concerned was demonstrated, but there were no particular differences in the intensities of the ventriculograms obtained. Morphological studies of the ventricles and histological examinations of the ventricular walls 1 month after injections of Dimer-X into the ventricles of dogs showed no abnormalities. In the clinical studies, ventriculography Dimer-X, performed on patients with diseases of the central nervous system, produced ventriculograms of good diagnostic value with no side effects, such as convulsions, apart from mild headache or vomiting in 4 instances. Ventriculography with Dimer-X was carried in 15 infants with myelomeningocele and progressive hydrocephalus. However, as was shown in a number of studies iocarmate produced moderate to severe arachnoiditis from myelography in primates. Early meningitis side effects following lumbar radiculography with iocarmate meglumine were demonstrated.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Lumbar myelography with meglumine iocarmate and metrizamide.
1975 May
Solute excretion during intravenous urography. A comparison of sodium iothalamate and sodium iocarmate (iothalamate dimer).
1975 Nov-Dec
Ventriculography with methylglucamine iocarmate (Dimer-X). Experimental and clinical study.
1976
Ionic composition and cardiotoxicity of dimeric contrast media at injection into the coronary arteries of rabbits.
1976 Jul
A clinical and experimental study of meglumine iocarmate in the subarachnoid space: a complication of positive contrast ventriculography.
1976 Mar
Water-soluble contrast radiculography of the lumbar region.
1976 Sep
Severity of postmyelographic arachnoiditis and concentration of meglumine locarmate in primates.
1978 Feb
Arachnoiditis from myelography with iopamidol, metrizamide, and iocarmate compared in the animal model.
1980 Nov-Dec
In vitro testing for the risk of arachnoiditis from myelographic contrast media.
1985 Aug
Patents

Sample Use Guides

1-5 ml Dimer-X (Iocarmic acid salt meglumine iocarmate) administered in patients aged 8 months to 62 years with diseases of the central nervous system
Route of Administration: Intracoronary
The effect of contrast media on protein and collagen production by fibroblasts in vitro was studied. Iocarmate added to the culture medium caused cells to produce more protein and collagen. The degree to which the contrast medium stimulated collagen production correlated with the risk of arachnoiditis from the intrathecal use of the contrast medium. Iocarmate was toxic to neurons in the concentration of 50 mmol/l and showed variable glial toxicity.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:21:10 GMT 2023
Edited
by admin
on Fri Dec 15 16:21:10 GMT 2023
Record UNII
2303MD51O1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IOCARMATE MEGLUMINE
USAN   WHO-DD  
USAN  
Official Name English
MP-2032 MEGLUMINE
Code English
MP 2032-MEGLUMINE
Code English
IOCARMATE MEGLUMINE [USAN]
Common Name English
MEGLUMINE IOCARMATE [MART.]
Common Name English
IOCARMIC ACID DI-N-METHYLGLUCAMINE SALT
MI  
Common Name English
MEGLUMINE IOCARMATE
MART.  
Common Name English
DIMER-X
Brand Name English
DIMERAY
Brand Name English
BENZOIC ACID, 3,3'-((1,6-DIOXO-1,6-HEXANEDIYL)DIIMINO)BIS(2,4,6-TRIIODO-5-((METHYLAMINO)CARBONYL)-, COMPOUND WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:2)
Common Name English
MP-2032-MEGLUMINE
Code English
Iocarmate meglumine [WHO-DD]
Common Name English
5,5'-(ADIPOYLDIIMINO)BIS(2,4,6-TRIIODO-N-METHYLISOPHTHALAMIC ACID) COMPOUND WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:2)
Common Name English
IOCARMIC ACID DI-N-METHYLGLUCAMINE SALT [MI]
Common Name English
MEGLUMINE IOCARMIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28500
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C75625
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
DRUG BANK
DBSALT002904
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID101009319
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
SMS_ID
100000077374
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
MERCK INDEX
m6323
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY Merck Index
PUBCHEM
23620992
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
MESH
C025504
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
EVMPD
SUB14236MIG
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
CAS
54605-45-7
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106389
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
FDA UNII
2303MD51O1
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
259-252-7
Created by admin on Fri Dec 15 16:21:10 GMT 2023 , Edited by admin on Fri Dec 15 16:21:10 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY