Basic information
- CAS
80529-93-7- Standard SMILES
O=C([O-])CN(CCN(CC(=O)[O-])CC(=O)[O-])CCN(CC(=O)[O-])CC(=O)[O-].[Gd+3].[H+].[H+]- InChIKey
IZOOGPBRAOKZFK-UHFFFAOYSA-K- Molecular formula
- C14H20GdN3O10
- Average molar mass
- 547.57 g/mol
- Monoisotopic mass
- 548.03898
Overview
A complex of gadolinium with a chelating agent, diethylenetriamine penta-acetic acid (DTPA see pentetic acid), that is given to enhance the image in cranial and spinal MRIs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p706)
Names & identifiers
- Preferred name
- Acide gadopentetique [French]
- IUPAC
- 2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;gadolinium(3+);hydron
- English name
- Gadopentetic acid
- Molecular formula
- C14H20GdN3O10
- Molecular weight
- 547.57
Names & synonyms
UNII-K2I13DR72LAcide gadopentetique [French]Acido gadopentetico [Spanish]Acidum gadopenteticum [Latin]Gadopentetic Acid [INN:BAN]Gadopentetic acid (Standard)orb1217633orb1307066HY-107353RHY-107353CS-0028202Gadolinate(2-), (N,N-bis(2-(bis(carboxymethyl)amino)ethyl)glycinato(5-))-, dihydrogen
Show more names
GADOPENTETATEGd-DTPAGadopenteticGd acid spraygadoliniumdtpaGadopentatic AcidGadopentetic acidAcido gadopenteticoAcide gadopentetiqueAcidum gadopenteticum
Database identifiers
- CAS
80529-93-7- PubChem CID
- 56841013
Properties
Computed structural properties
- Topological polar surface area
- 210 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 0
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 487
Physicochemical properties
- Melting point
- 129 °C · 129 °C (dec.)(lit.)
- storage temp.
- Room Temperature
- solubility
- Water (Slightly)
- form
- Solid
- color
- White
- InChI
- InChI=1S/C14H23N3O10.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);/q;+3/p-3
- InChIKey
- IZOOGPBRAOKZFK-UHFFFAOYSA-K
- SMILES
- N(CC([O-])=O)(CCN(CC([O-])=O)CC(=O)O)CCN(CC([O-])=O)CC(=O)O.[Gd+3]
- FDA UNII
- 2 I13DR72L · K2I13DR72L
- NCI Dictionary of Cancer Terms
- Gd-DTPA
- ATC code
- 8 CA01 · V08CA01
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
Based on the behavior of protons when placed in a strong magnetic field, which is interpreted and transformed into images by magnetic resonance (MR) instruments. MR images are based primarily on proton density and proton relaxation dynamics. MR instruments are sensitive to two different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and T2 (spin-spin or transverse relaxation time). Paramagnetic agents contain one or more unpaired electrons that enhance the T1 and T2 relaxation rates of protons in their molecular environment. The proton relaxation effect (PRE) of an unpaired electron is 700 times stronger than that of a proton itself. In MRI, visualization of normal and pathological brain tissue depends in part on variations in the radio frequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadopentetate dimeglumine shortens the T1 and T2 relaxation times in tissues where it accumulates. In the central nervous system (CNS), gadopentetate dimeglumine enhances visualization of normal tissues that lack a blood-brain barrier, such as the pituitary gland and the meninges. Gadopentetate dimeglumine does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in CNS lesions that have not caused an abnormal blood-brain barrier (e.g., cysts, mature post-operative scars). Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadopentetate dimeglumine in lesions such as neoplasms, abscesses, and subacute infarcts. Outside the CNS, gadopentetate dimeglumine rapidly reaches equilibrium in the interstitial compartment and enhances signal in all tissues as a function of delivery and size of the interstitial compartment. This compound has also been found to inhibit human erythrocyte 6-phosphogluconate dehydrogenase.
Biological Half-LifeDistribution half life 12 minutes, elimination half 100 minutes
Metabolism/MetabolitesNo detectable biotransformation or decomposition.
Absorption, Distribution and Excretion
Gadopentetate is exclusively eliminated in the urine with 83 ± 14% (mean ± SD) of the dose excreted within 6 hours and 91 ± 13% (mean ± SD) by 24 hours, post-injection.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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