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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19FN2O2
Molecular Weight 302.3434
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRIRALFINAMIDE

SMILES

C[C@H](NCC1=CC=C(OCC2=CC=CC=C2F)C=C1)C(N)=O

InChI

InChIKey=BHJIBOFHEFDSAU-LBPRGKRZSA-N
InChI=1S/C17H19FN2O2/c1-12(17(19)21)20-10-13-6-8-15(9-7-13)22-11-14-4-2-3-5-16(14)18/h2-9,12,20H,10-11H2,1H3,(H2,19,21)/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H19FN2O2
Molecular Weight 302.3434
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.prnewswire.com/news-releases/newron-announces-positive-results-with-ralfinamide-from-phase-ii-trial-in-neuropathic-pain-74976442.html

Priralfinamide, also known as Ralfinamide, FCE-26742A; NW-1029; PNU-0154339E, is a Na-channel blocker for the treatment of neuropathic pain and other pain conditions such as post-operative dental pain. It has a relatively complex pharmacology, acting as a mixed voltage-gated sodium channel blocker (including Nav1.7), N-type calcium channel blocker, noncompetitive NMDA receptor antagonist, and monoamine oxidase B inhibitor. Priralfinamide is in phase Ⅲ clinical trials by Newron for the treatment of chronic neuropathic pain.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.28 μg/mL
320 mg single, oral
dose: 320 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRIRALFINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
41.3 mg × h/L
320 mg single, oral
dose: 320 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRIRALFINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.7 h
320 mg single, oral
dose: 320 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRIRALFINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
320 mg single, oral
dose: 320 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRIRALFINAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Other AEs: numbness of throat, flu symptoms...
Other AEs:
numbness of throat (1 pt)
flu symptoms (1 pt)
Alanine aminotransferase increase (mild, 1 pt)
aspartate aminotransferase (mild, 1 pt)
Dizziness (3 patients)
Numbness of tongue (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
flu symptoms 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
numbness of throat 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Numbness of tongue 2 patients
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Dizziness 3 patients
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Alanine aminotransferase increase mild, 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
aspartate aminotransferase mild, 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Ralfinamide. Newron Pharmaceuticals.
2004 Oct
Analysis of human Nav1.8 expressed in SH-SY5Y neuroblastoma cells.
2005 Dec 28
Gateways to clinical trials.
2005 Jul-Aug
Functional and pharmacological properties of human and rat NaV1.8 channels.
2009 Apr
Patents

Sample Use Guides

Priralfinamide administered orally at rising doses of 80 - 320 mg/day
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Priralfinamide (3–200 uM) inhibition of tetrodotoxinresistant and tetrodotoxin-sensitive peak current amplitudes (tonic block) was strictly concentration dependent. Tetrodotoxin-resistant currents, evoked from a pre-conditioning potential giving maximal current availability (90 mV), were inhibited by ralfinamide with an IC50 value of 72 uM https://www.ncbi.nlm.nih.gov/pubmed/15763243
In capsaicin-responsive tonic firing nociceptive dorsal root ganglion neurons of adult rats, priralfinamide (25 uM) reduced the number of action potentials (APs) from 10.6+/-1.8 to 2.6+/-0.7 APs/600 ms
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:47:25 UTC 2023
Edited
by admin
on Sat Dec 16 16:47:25 UTC 2023
Record UNII
3LPF0S0GVV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRIRALFINAMIDE
INN  
INN  
Official Name English
priralfinamide [INN]
Common Name English
(2S)-2-(4-(2-FLUOROBENZYLOXY)BENZYLAMINO)PROPANAMIDE
Systematic Name English
PNU-0154339E
Code English
NW1029
Code English
NW-1029
Code English
RALFINAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C75074
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID70158406
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107771
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
FDA UNII
3LPF0S0GVV
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
DRUG BANK
DB06649
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
SMS_ID
100000089211
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
EVMPD
SUB25211
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
INN
8338
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
WIKIPEDIA
Ralfinamide
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
PUBCHEM
5745207
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
CAS
133865-88-0
Created by admin on Sat Dec 16 16:47:25 UTC 2023 , Edited by admin on Sat Dec 16 16:47:25 UTC 2023
PRIMARY
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