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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25NO3
Molecular Weight 327.4182
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRAXOPRODIL

SMILES

C[C@@]([H])([C@]([H])(c1ccc(cc1)O)O)N2CCC(CC2)(c3ccccc3)O

InChI

InChIKey=QEMSVZNTSXPFJA-HNAYVOBHSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H25NO3
Molecular Weight 327.4182
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: # Pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
674 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1370 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
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
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

Doses

DosePopulationAdverse 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)
Carbidopa
Sources: Page: p.5, 13
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...
Other AEs:
Abnormal thinking (83.3%)
Sources: Page: p.5, 13
AEs

AEs

AESignificanceDosePopulation
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)
Carbidopa
Sources: Page: p.5, 13
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex.
2000 Jan 28
Characterization of N-methyl-D-aspartate receptor subunits responsible for postoperative pain.
2004 Oct 25
Arthritis and pain. Future targets to control osteoarthritis pain.
2007
Patents

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:08:24 UTC 2021
Edited
by admin
on Sat Jun 26 05:08:24 UTC 2021
Record UNII
UTC046R5HM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRAXOPRODIL
INN   WHO-DD  
INN  
Official Name English
TRAXOPRODIL [WHO-DD]
Common Name English
1-PIPERIDINEETHANOL, 4-HYDROXY-.ALPHA.-(4-HYDROXYPHENYL)-.BETA.-METHYL-4-PHENYL-, (S-(R*,R*))-
Common Name English
CP-101606
Code English
TRAXOPRODIL [INN]
Common Name English
(.ALPHA.S,.BETA.S)-4-HYDROXY-.ALPHA.-(P-HYDROXYPHENYL)-.BETA.-METHYL-4-PHENYL-1-PIPERIDINEETHANOL
Common Name English
CP-101,606
Code English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C87769
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
INN
8053
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
FDA UNII
UTC046R5HM
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
EPA CompTox
134234-12-1
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
ChEMBL
CHEMBL17350
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
PUBCHEM
219101
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
WIKIPEDIA
TRAXOPRODIL
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
CAS
134234-12-1
Created by admin on Sat Jun 26 05:08:25 UTC 2021 , Edited by admin on Sat Jun 26 05:08:25 UTC 2021
PRIMARY
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EXCRETED UNCHANGED
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE

INTRAVENOUS ADMINISTRATION

IN CYP2D6 PHENOTYPE: EXTENSIVE METABOLIZERS

Tmax PHARMACOKINETIC SINGLE DOSE

INTRAVENOUS ADMINISTRATION

IN CYP2D6 PHENOTYPE: EXTENSIVE METABOLIZERS

Tmax PHARMACOKINETIC IN CYP2D6 PHENOTYPE: POOR METABOLIZERS

INTRAVENOUS ADMINISTRATION

SINGLE DOSE

Biological Half-life PHARMACOKINETIC SINGLE DOSE

IN CYP2D6 PHENOTYPE: POOR METABOLIZERS

INTRAVENOUS ADMINISTRATION