All Photos(2)
Synonym(s):
Traxoprodil; (1S,2S)-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol; CP-101606
Empirical Formula (Hill Notation):
C20H25NO3
CAS Number:
Molecular Weight:
327.42
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥98% (HPLC)
form
powder
optical activity
[α]/D +50 to +60° (c=1, MeOH)
color
white to tan
solubility
DMSO: ≥35 mg/mL
storage temp.
2-8°C
SMILES string
C[C@@H]([C@@H](O)c1ccc(O)cc1)N2CCC(O)(CC2)c3ccccc3
InChI
1S/C20H25NO3/c1-15(19(23)16-7-9-18(22)10-8-16)21-13-11-20(24,12-14-21)17-5-3-2-4-6-17/h2-10,15,19,22-24H,11-14H2,1H3/t15-,19+/m0/s1
InChI key
QEMSVZNTSXPFJA-HNAYVOBHSA-N
Gene Information
human ... GRIN1(2902) , GRIN2B(2904)
Related Categories
General description
CP-101,606 (Traxoprodil) is a substituted 4-phenylpiperidine and is localized in the fore brain neurons.
Application
CP-101,606 has been used as a N-methyl-D-aspartate (NMDA) receptor antagonist to study its role in recovery of spinal cord injuries.
Biochem/physiol Actions
CP-101,606 (Traxoprodil) plays a role in inhibiting glutamate-induced death in rats. It may exhibit therapeutic effects against human ischemia and neurodegenerative disorders. Traxoprodil is metabolized by cytochrome P450 (CYP) 2D6.
Traxoprodil (CP-101,606) is a potent noncompetitive antagonist of N-methyl-D-aspartate (NMDA) receptors, selective for the NR2B subunit. It has been shown to be neuroprotective in animal models of brain injury and stroke.
Features and Benefits
This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Robert Becker et al.
Psychopharmacology, 236(12), 3451-3463 (2019-07-04)
The N-methyl-D-aspartate receptor (NMDAR) antagonist ketamine is known to have not only a rapid antidepressant effect but also dissociative side effects. Traxoprodil and lanicemine, also NMDA antagonists, are candidate antidepressant drugs with fewer side effects. In order to understand their
Absolute oral bioavailability of traxoprodil in cytochrome P450 2D6 extensive and poor metabolisers.
Timothy J Taylor et al.
Clinical pharmacokinetics, 45(10), 989-1001 (2006-09-21)
Traxoprodil, a substituted 4-phenylpiperidine, is an N-methyl-D-aspartate (NMDA) receptor antagonist that is selective for receptors containing the NR2B subunit. In vivo and in vitro studies examining the disposition of traxoprodil have demonstrated that it is mainly metabolised by cytochrome P450
Weronika Stasiuk et al.
Journal of neural transmission (Vienna, Austria : 1996), 124(3), 387-396 (2016-12-03)
Pre-clinical and clinical studies indicated that a blockade of the NMDA receptor complex creates new opportunities for the treatment of affective disorders, including depression. The aim of the present study was to assess the influence of traxoprodil (10 mg/kg) on the
Chandra Prakash et al.
Drug metabolism and disposition: the biological fate of chemicals, 35(8), 1350-1364 (2007-05-15)
Disposition of traxoprodil ({1-[2-hydroxy-2-(4-hydroxy-phenyl)-1-methyl-ethyl]-4-phenyl-piperidin-4-ol}mesylate; TRX), a selective antagonist of the N-methyl-d-aspartate class of glutamate receptors, was investigated in rats and dogs after administration of a single i.v. bolus dose of [(14)C]TRX. Total mean recoveries of the radiocarbon were 92.5 and
Bo Chen et al.
Cell, 174(3), 521-535 (2018-07-24)
Many human spinal cord injuries are anatomically incomplete but exhibit complete paralysis. It is unknown why spared axons fail to mediate functional recovery in these cases. To investigate this, we undertook a small-molecule screen in mice with staggered bilateral hemisections
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