NAV

Motexafin gadolinium

Identification

Generic Name
Motexafin gadolinium
DrugBank Accession Number
DB05428
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 1148.4
Monoisotopic: 1148.43167757
Chemical Formula
C52H72GdN5O14
Synonyms
  • Gadolinium texaphyrin
  • Motexafin gadolinium
External IDs
  • PCI 0120
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Pharmacology

Indication

Investigated for use/treatment in brain cancer, cancer/tumors (unspecified), lung cancer, and lymphoma (non-hodgkin's).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

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.

TargetActionsOrganism
UThioredoxin reductase 1, cytoplasmicNot AvailableHumans
UThioredoxin reductase 2, mitochondrialNot AvailableHumans
URibonucleoside-diphosphate reductase subunit M2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Motexafin gadolinium is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Motexafin gadolinium is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Motexafin gadolinium is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Motexafin gadolinium is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Motexafin gadolinium is combined with Bupivacaine.
Food Interactions
Not Available

Products

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International/Other Brands
Xcytrin

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
0BG5NE3APZ
CAS number
246252-06-2
InChI Key
VAZLWPAHMORDGR-WRIGXHCHSA-L
InChI
InChI=1S/C48H66N5O10.2C2H4O2.Gd/c1-7-35-36(8-2)40-28-42-38(12-10-14-55)34(4)46(53-42)32-50-44-30-48(63-26-24-61-22-20-59-18-16-57-6)47(62-25-23-60-21-19-58-17-15-56-5)29-43(44)49-31-45-33(3)37(11-9-13-54)41(52-45)27-39(35)51-40;2*1-2(3)4;/h27-32,54-55H,7-26H2,1-6H3;2*1H3,(H,3,4);/q-1;;;+3/p-2/b39-27-,40-28-,41-27-,42-28-,45-31-,46-32-,49-31+,49-43+,50-32+,50-44+;;;
IUPAC Name
gadolinium(3+) 4,5-diethyl-9,24-bis(3-hydroxypropyl)-16,17-bis({2-[2-(2-methoxyethoxy)ethoxy]ethoxy})-10,23-dimethyl-13,20,25,26,27-pentaazapentacyclo[20.2.1.1^{3,6}.1^{8,11}.0^{14,19}]heptacosa-1(25),2,4,6,8(26),9,11,13,15,17,19,21,23-tridecaen-27-ide diacetate
SMILES
[Gd+3].CC([O-])=O.CC([O-])=O.CCC1=C(CC)/C2=C/C3=N/C(=C\N=C4/C=C(OCCOCCOCCOC)C(OCCOCCOCCOC)=C/C/4=N\C=C4/N=C(/C=C\1\[N-]\2)C(CCCO)=C4C)/C(C)=C3CCCO

References

General References
  1. Evens AM: Motexafin gadolinium: a redox-active tumor selective agent for the treatment of cancer. Curr Opin Oncol. 2004 Nov;16(6):576-80. [Article]
  2. Forouzannia A, Richards GM, Khuntia D, Mehta MP: Motexafin gadolinium: a novel radiosensitizer for brain tumors. Expert Rev Anticancer Ther. 2007 Jun;7(6):785-94. [Article]
PubChem Compound
158385
PubChem Substance
175427002
ChemSpider
139341
ChEBI
50161
Wikipedia
Motexafin_gadolinium

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBrain Neoplasm / Metastatic Cancer / Non-Small Cell Lung Carcinoma1
2CompletedTreatmentAdenocarcinomas / Lung Neoplasm / Non-Small Cell Lung Carcinoma1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentGenitourinary tract neoplasm / Renal Cell Carcinoma (RCC) / Renal Neoplasms / Urologic Neoplasms1
2CompletedTreatmentLymphoma / Non-Hodgkin's Lymphoma (NHL) / Non-Hodgkin's Lymphomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0122 mg/mLALOGPS
logP4.95ALOGPS
logP6.76Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)15.62Chemaxon
pKa (Strongest Basic)2.45Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area178.75 Å2Chemaxon
Rotatable Bond Count28Chemaxon
Refractivity243.08 m3·mol-1Chemaxon
Polarizability103.73 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5376
Blood Brain Barrier-0.715
Caco-2 permeable-0.5913
P-glycoprotein substrateSubstrate0.8533
P-glycoprotein inhibitor INon-inhibitor0.6742
P-glycoprotein inhibitor IINon-inhibitor0.8876
Renal organic cation transporterNon-inhibitor0.7757
CYP450 2C9 substrateNon-substrate0.8708
CYP450 2D6 substrateNon-substrate0.8061
CYP450 3A4 substrateSubstrate0.5704
CYP450 1A2 substrateNon-inhibitor0.6095
CYP450 2C9 inhibitorNon-inhibitor0.7021
CYP450 2D6 inhibitorNon-inhibitor0.8511
CYP450 2C19 inhibitorNon-inhibitor0.7157
CYP450 3A4 inhibitorNon-inhibitor0.5474
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8753
Ames testNon AMES toxic0.6036
CarcinogenicityNon-carcinogens0.9027
BiodegradationNot ready biodegradable0.8517
Rat acute toxicity2.5734 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8697
hERG inhibition (predictor II)Non-inhibitor0.7296
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-306.5115768
predicted
DarkChem Lite v0.1.0
[M+H]+304.6440768
predicted
DarkChem Lite v0.1.0
[M+Na]+305.8928768
predicted
DarkChem Lite v0.1.0

Targets

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Details1. Thioredoxin reductase 1, cytoplasmic
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thioredoxin-disulfide reductase activity
Specific Function
Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enha...
Gene Name
TXNRD1
Uniprot ID
Q16881
Uniprot Name
Thioredoxin reductase 1, cytoplasmic
Molecular Weight
70905.58 Da
Details2. Thioredoxin reductase 2, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thioredoxin-disulfide reductase activity
Specific Function
Maintains thioredoxin in a reduced state. Implicated in the defenses against oxidative stress. May play a role in redox-regulated cell signaling.
Gene Name
TXNRD2
Uniprot ID
Q9NNW7
Uniprot Name
Thioredoxin reductase 2, mitochondrial
Molecular Weight
56506.275 Da
Details3. Ribonucleoside-diphosphate reductase subunit M2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribonucleoside-diphosphate reductase activity, thioredoxin disulfide as acceptor
Specific Function
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. Inhibits Wnt signaling.
Gene Name
RRM2
Uniprot ID
P31350
Uniprot Name
Ribonucleoside-diphosphate reductase subunit M2
Molecular Weight
44877.25 Da

Drug created at November 18, 2007 18:24 / Updated at January 14, 2023 19:03