Motexafin gadolinium
Basic information
- CAS
246252-06-2- Standard SMILES
CC(=O)[O-].CC(=O)[O-].CCc1c(CC)c2cc3nc(cnc4cc(OCCOCCOCCOC)c(OCCOCCOCCOC)cc4ncc4nc(cc1[n-]2)C(CCCO)=C4C)C(C)=C3CCCO.[Gd+3]- InChIKey
VAZLWPAHMORDGR-UHFFFAOYSA-L- Molecular formula
- C52H72GdN5O14
- Average molar mass
- 1,148.4 g/mol
- Monoisotopic mass
- 1,148.43169
Overview
Motexafin gadolinium is studied in the treatment of cancer by Pharmacyclics. It may make tumor cells more sensitive to radiation therapy, improve tumor images using magnetic resonance imaging (MRI), and kill cancer cells. It belongs to the family of drugs called metalloporphyrin complexes. Also called gadolinium texaphyrin.
Names & identifiers
- Preferred name
- Motexafin gadolinium
- IUPAC
- 3-[4,5-diethyl-24-(3-hydroxypropyl)-16,17-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-10,23-dimethyl-13,20,25,26-tetraza-27-azanidapentacyclo[20.2.1.13,6.18,11.014,19]heptacosa-1(25),2,4,6,8(26),9,11,13,15,17,19,21,23-tridecaen-9-yl]propan-1-ol;gadolinium(3+);diacetate
- English name
- XCYTRIN
- Molecular formula
- C52H72GdN5O14
- Molecular weight
- 1148.41
Names & synonyms
Motexafin gadoliniumGadolinium texaphyrinXcytrinPCI-0120246252-06-23-[4,5-Diethyl-24-(3-hydroxypropyl)-16,17-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-10,23-dimethyl-13,20,25,26-tetraza-27-azanidapentacyclo[20.2.1.13,6.18,11.014,19]heptacosa-1(25),2,4,6,8(26),9,11,13,15,17,19,21,23-tridecaen-9-yl]propan-1-ol;gadolinium(3+);diacetate0BG5NE3APZMotexafin gadolinium anhydrousSCHEMBL29355268MOTEXAFIN GADOLINIUM [MI]DB05428Q11786072
Show more names
PCI0120PCI 0120API-GP 3Gd texaphyrinGd-TexgadoliniumVAZLWPAHMORDGR-UHFFFAOYSA-L
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 245 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 19
- Rotatable bonds
- 28
- Heavy atoms
- 72
- Formal charge
- 0
- Complexity
- 1,900
Physicochemical properties
- FDA UNII
- 0 BG5NE3APZ · 0BG5NE3APZ
- NCI Drug Dictionary
- Xcytrin
Chemistry & industry
Pharmacology
Mechanism of Action
Motexafin gadolinium (Xcytrin) is Pharmacyclics' most advanced anti-cancer product candidate, a small-molecule drug with a novel mechanism of action. Xcytrin accumulates selectively in cancer cells due to their increased rates of metabolism. Once inside the cell, Xcytrin induces apoptosis (programmed cell death) by disrupting redox-dependent pathways. Xcytrin inhibits the enzyme thioredoxin reductase, which is a tumor growth promoter. This mechanism provides the opportunity to use Xcytrin in a wide range of cancers. Xcytrin is paramagnetic, and therefore is detectable by magnetic resonance imaging (MRI), allowing the visualization of the drug in tumors.
Applications
UsesMotexafin gadolinium (PCI 0120) is a potent antitumor agent. Motexafin gadolinium is a specific texaphyrin in complex with gadolinium(III). Motexafin gadolinium increases intracellular ROS production. Motexafin gadolinium enhances sensitivity of tumor cells to ionizing radiation[1][2][3].
Related reactions
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Compound notes
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