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 | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: Page: p.995 |
healthy, ADULT n = 11 Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Population Size: 11 Sources: Page: p.995 |
|
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 Co-administed with:: levodopa(25mg, was administered orally) Sources: Page: p.5, 13Carbidopa |
unhealthy, ADULT n = 12 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 12 Sources: Page: p.5, 13 |
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 Co-administed with:: levodopa(25mg, was administered orally) Sources: Page: p.5, 13Carbidopa |
unhealthy, ADULT n = 12 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 12 Sources: Page: p.5, 13 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antioxidant-accelerated oxidative degradation: a case study of transition metal ion catalyzed oxidation in formulation. | 2004 |
|
| Gateways to clinical trials. | 2004 Apr |
|
| Characterization of N-methyl-D-aspartate receptor subunits involved in acute ammonia toxicity. | 2004 Jan |
|
| Role of NMDA receptor subtypes in the induction of catalepsy and increase in Fos protein expression after administration of haloperidol. | 2004 Jun 11 |
|
| Characterization of N-methyl-D-aspartate receptor subunits responsible for postoperative pain. | 2004 Oct 25 |
|
| Evidence for improved performance in cognitive tasks following selective NR2B NMDA receptor antagonist pre-treatment in the rat. | 2005 Apr |
|
| The effect of the selective NMDA receptor antagonist traxoprodil in the treatment of traumatic brain injury. | 2005 Dec |
|
| Absolute oral bioavailability of traxoprodil in cytochrome P450 2D6 extensive and poor metabolisers. | 2006 |
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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I23V4CCC9V
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Validated (UNII)
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