Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H25NO3.CH4O3S |
| Molecular Weight | 423.523 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.C[C@@H]([C@@H](O)C1=CC=C(O)C=C1)N2CCC(O)(CC2)C3=CC=CC=C3
InChI
InChIKey=OZBWUANKVIMZIA-WRRDZZDISA-N
InChI=1S/C20H25NO3.CH4O3S/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;1-5(2,3)4/h2-10,15,19,22-24H,11-14H2,1H3;1H3,(H,2,3,4)/t15-,19+;/m0./s1
| Molecular Formula | C20H25NO3 |
| Molecular Weight | 327.4174 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11249721
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11249721
Traxoprodil (CP-101,606) is a potent, selective N-Methyl-D-aspartate (NMDA) receptor (NR2B subunit) antagonist under development by Pfizer for its potential as a neuroprotectant in head injury and neurodegenerative disease. It is in phase II trials in the US and in phase I in Japan for the potential treatment of head injury, such as, Depressive Disorder, Major and Parkinson's Disease. CP-101,606 does not protect against glutamate-induced neurotoxicity in cultured cerebellar neurons, up to a dose of 10 uM. These results are consistent with CP-101,606 being a potent NMDA antagonist, selective for the type of NMDA receptor associated with the hippocampus. Some further investigation revealed that CP-101,606 was associated with a dose-related dissociation and amnesia. These results support the hypothesis that glutamate antagonists may be useful antidyskinetic agents. However, future studies will have to determine if the benefits of dyskinesia suppression can be achieved without adverse cognitive effects.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
674 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
246 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1370 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
856 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16984212 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
TRAXOPRODIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg single, oral Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
0.75 mg/kg 1 times / hour multiple, intravenous Highest studied dose Dose: 0.75 mg/kg, 1 times / hour Route: intravenous Route: multiple Dose: 0.75 mg/kg, 1 times / hour Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Abnormal thinking... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abnormal thinking | 83.3% | 0.75 mg/kg 1 times / hour multiple, intravenous Highest studied dose Dose: 0.75 mg/kg, 1 times / hour Route: intravenous Route: multiple Dose: 0.75 mg/kg, 1 times / hour Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Forelimb dyskinesia mediated by high-frequency stimulation of the subthalamic nucleus is linked to rapid activation of the NR2B subunit of N-methyl-D-aspartate receptors. | 2010-08 |
|
| Innovative approaches to treatment - refractory depression: The ketamine story. | 2010-04 |
|
| Glutamate-based antidepressants: 20 years on. | 2009-11 |
|
| Effects of a NR2B selective NMDA glutamate antagonist, CP-101,606, on dyskinesia and Parkinsonism. | 2008-10-15 |
|
| The phencyclidine-like discriminative stimulus effects and reinforcing properties of the NR2B-selective N-methyl-D-aspartate antagonist CP-101 606 in rats and rhesus monkeys. | 2007-12 |
|
| Metabolism, distribution and excretion of a selective N-methyl-D-aspartate receptor antagonist, traxoprodil, in rats and dogs. | 2007-08 |
|
| Effects of pan- and subtype-selective N-methyl-D-aspartate receptor antagonists on cortical spreading depression in the rat: therapeutic potential for migraine. | 2007-05 |
|
| Arthritis and pain. Future targets to control osteoarthritis pain. | 2007 |
|
| Absolute oral bioavailability of traxoprodil in cytochrome P450 2D6 extensive and poor metabolisers. | 2006 |
|
| The effect of the selective NMDA receptor antagonist traxoprodil in the treatment of traumatic brain injury. | 2005-12 |
|
| Evidence for improved performance in cognitive tasks following selective NR2B NMDA receptor antagonist pre-treatment in the rat. | 2005-04 |
|
| Characterization of N-methyl-D-aspartate receptor subunits responsible for postoperative pain. | 2004-10-25 |
|
| Role of NMDA receptor subtypes in the induction of catalepsy and increase in Fos protein expression after administration of haloperidol. | 2004-06-11 |
|
| Gateways to clinical trials. | 2004-04 |
|
| Characterization of N-methyl-D-aspartate receptor subunits involved in acute ammonia toxicity. | 2004-01 |
|
| Antioxidant-accelerated oxidative degradation: a case study of transition metal ion catalyzed oxidation in formulation. | 2004 |
|
| Metabolism, pharmacokinetics, and excretion of a highly selective N-methyl-D-aspartate receptor antagonist, traxoprodil, in human cytochrome P450 2D6 extensive and poor metabolizers. | 2003-01 |
|
| Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex. | 2000-01-28 |
Patents
Sample Use Guides
CP 101,606 (TRAXOPRODIL) was administered at 0.25 mg/kg/hr for 2 hours followed by 0.12 mg/kg/hr for 2 hours, targeting a minimum plasma concentration of 60 ng/ml. “High dose” CP 101,606 was administered at 0.75 mg/kg/hr for 2 hours and then at 0.36 mg/kg/hr for 2 hours, targeting a minimum plasma concentration of 200 ng/ml. Matching placebo infusions were administered the control day. The study drug (CP-101,606 or placebo) were infused at a same infusion rates for each subject via a dedicated intravenous line.
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 21:32:56 GMT 2025
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| Record UNII |
I23V4CCC9V
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| Record Status |
Validated (UNII)
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| Record Version |
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