Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H24F2N2O.C7H8O3S |
| Molecular Weight | 494.594 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.CCNC(=O)[C@H]2C[C@](F)(C2)C3=CC(F)=C(CN4CCCC4)C=C3
InChI
InChIKey=IKAYTZLLIWAEDV-WXWMPIANSA-N
InChI=1S/C18H24F2N2O.C7H8O3S/c1-2-21-17(23)14-10-18(20,11-14)15-6-5-13(16(19)9-15)12-22-7-3-4-8-22;1-6-2-4-7(5-3-6)11(8,9)10/h5-6,9,14H,2-4,7-8,10-12H2,1H3,(H,21,23);2-5H,1H3,(H,8,9,10)/t14-,18-;
| Molecular Formula | C18H24F2N2O |
| Molecular Weight | 322.3928 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C7H8O3S |
| Molecular Weight | 172.202 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: http://www.pfizer.com/sites/default/files/product-pipeline/pipeline_2011_0228.pdf
Curator's Comment: http://www.pfizer.com/sites/default/files/product-pipeline/pipeline_2011_0228.pdf
PF-03654746 is a potent, selective antagonist of the human H3 receptor, developed by Pfizer. It was in the clinical trial phase II for the treatment of excessive daytime sleepiness (EDS) associated with narcolepsy, Tourette syndrome as well as potential anti-allergy applications and in phase I of clinical trial for the treatment of Schizophrenia and Alzheimer's disease, but these investigations were discontinued.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL264 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14020 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21928839 |
300 mg/kg 1 times / day multiple, oral dose: 300 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PF-03654746 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
189000 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21928839 |
300 mg/kg 1 times / day multiple, oral dose: 300 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PF-03654746 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21928839 |
300 mg/kg 1 times / day multiple, oral dose: 300 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PF-03654746 plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Discovery of two clinical histamine H(3) receptor antagonists: trans-N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidinylmethyl)phenyl]cyclobutanecarboxamide (PF-03654746) and trans-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-N-(2-methylpropyl)cyclobutanecarboxamide (PF-03654764). | 2011 Nov 10 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT01346163?term=PF-03654746&rank=4
excessive daytime sleepiness (EDS) associated with narcolepsy: Each patient will receive PF-03654746 tablets in a fixed dose titration schedule beginning at 0.25 mg QD for 5 days; then up to 0.50 mg QD for another 5 days; and up to 1.0 mg QD for an additional 5 days
Schizophrenia: PF-03654746 will be administered in a flexible titration regimen, beginning with 0.5 mg/d. If 0.5 mg/d is well tolerated, the dose will be increased to 1.0 mg/d after 5 days. If 1.0 mg/d is not well tolerated, the dose will be decreased to 0.5 mg/d, with the goal of achieving a stable dose of PF-03654746 within the first two weeks of dosing and avoiding further dose changes during the final week of dosing.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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| Record UNII |
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| Record Status |
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