U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Inhibitor
8297
Blocker
537
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.28 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21071997/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21071997/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21071997/
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21071997/
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:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
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:
https://pubmed.ncbi.nlm.nih.gov/21071997
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:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
numbness of throat 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
Numbness of tongue 2 patients
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
Dizziness 3 patients
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
Alanine aminotransferase increase mild, 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
aspartate aminotransferase mild, 1 pt
320 mg single, oral (unknown)
Studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21071997
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY114296
https://www.001chemical.com/chem/search?q=DY114296
1PlusChem LLC
1P0028WQ
https://www.1pchem.com/search?query=1P0028WQ
1PlusChem LLC
1P009E4F
https://www.1pchem.com/search?query=1P009E4F
AK Scientific
0394AB
https://aksci.com/item_detail.php?cat=0394AB
AK Scientific
6134AA
https://aksci.com/item_detail.php?cat=6134AA
Alfa Chemistry
11936
http://www.alfa-chemistry.com/search.aspx?q=11936
Alfa Chemistry
AFI202825454
http://www.alfa-chemistry.com/search.aspx?q=AFI202825454
Angene
AGN-PC-0PK5KU
http://www.angenechemical.com/productshow/AGN-PC-0PK5KU.html
Angene
AGN-PC-0QT7XA
http://www.angenechemical.com/productshow/AGN-PC-0QT7XA.html
AstaTech
C15260
http://astatechinc.com/CPSResult.php?CRNO=C15260
AstaTech
F12108
http://astatechinc.com/CPSResult.php?CRNO=F12108
BLD Pharm
BD234099
http://www.bldpharm.com/search/Search.html?keyword=BD234099
BOC Sciences
202825-45-4
http://www.bocsci.com/description.asp?cas=202825-45-4
Chem Scene
CS-0021330
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0021330
Chem Scene
CS-0021517
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0021517
ChemShuttle
172375
https://www.chemshuttle.com/catalogsearch/result/?q=172375
Combi-Blocks
QN-9990
http://www.combi-blocks.com/cgi-bin/find.cgi?QN-9990
Fluorochem
232600
http://www.fluorochem.co.uk/Products/Product?code=232600
Fluorochem
315691
http://www.fluorochem.co.uk/Products/Product?code=315691
Hairui
RAXM015
http://www.hairuichem.com/en/product/search.do?q=RAXM015
KeyOrganics
DS-18607
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-18607
Lab Network
LN02009533
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02009533
Matrix Scientific
95353
http://www.matrixscientific.com/095353.html
MedChem Express
HY-101437
https://www.medchemexpress.com/search.html?q=HY-101437&ft=&fa=&fp=
MedChem Express
HY-101437A
https://www.medchemexpress.com/search.html?q=HY-101437A&ft=&fa=&fp=
MolPort
MolPort-023-277-041
https://www.molport.com/shop/molecule-link/MolPort-023-277-041
MolPort
MolPort-023-334-032
https://www.molport.com/shop/molecule-link/MolPort-023-334-032
MolPort
MolPort-047-133-871
https://www.molport.com/shop/molecule-link/MolPort-047-133-871
Molcore
MC114296
http://www.molcore.com/CatMC114296.html
MuseChem
M117811
https://www.musechem.com/product/M117811.html
MuseChem
R040315
https://www.musechem.com/product/R040315.html
TargetMol
T7349
https://www.targetmol.com/search?keyword=T7349
Tocris
4029
https://www.tocris.com/search.php?Type=QuickSearch&Value=4029
Toronto Research Chemicals
R075000
https://www.trc-canada.com/product-detail/?CatNum=R075000
Wonderchem
WD053O7
http://www.wonder-chem.com/search.html?text=WD053O7
Wonderchem
WD05JPL
http://www.wonder-chem.com/search.html?text=WD05JPL
eMolecules
300600840
https://orderbb.emolecules.com/search/#?query=300600840
eMolecules
36500872
https://orderbb.emolecules.com/search/#?query=36500872
eMolecules
44470330
https://orderbb.emolecules.com/search/#?query=44470330
eNovation Chemicals
D746959
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D746959&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-6020329217
https://mcule.com/MCULE-6020329217/
mcule
MCULE-6969894121
https://mcule.com/MCULE-6969894121/
PubMed

PubMed

TitleDatePubMed
Analysis of human Nav1.8 expressed in SH-SY5Y neuroblastoma cells.
2005 Dec 28
Functional and pharmacological properties of human and rat NaV1.8 channels.
2009 Apr
Disposition and metabolism of ralfinamide, a novel Na-channel blocker, in healthy male volunteers.
2010
Patents

Patents

08076515
1
08278485
1
08530701
1
08846763
1

Sample Use Guides

In Vivo Use Guide
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 GMT 2023
Edited
by admin
on Sat Dec 16 16:47:25 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C75074
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID70158406
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107771
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
FDA UNII
3LPF0S0GVV
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
DRUG BANK
DB06649
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
SMS_ID
100000089211
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
EVMPD
SUB25211
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
INN
8338
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
WIKIPEDIA
Ralfinamide
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
PUBCHEM
5745207
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
CAS
133865-88-0
Created by admin on Sat Dec 16 16:47:25 GMT 2023 , Edited by admin on Sat Dec 16 16:47:25 GMT 2023
PRIMARY
Related Record Type Details
SODIUM CHANNEL PROTEIN TYPE 10 SUBUNIT ALPHA
TARGET -> INHIBITOR
NMDA RECEPTOR
TARGET -> INHIBITOR
SODIUM CHANNEL PROTEIN TYPE 9 SUBUNIT ALPHA
TARGET -> INHIBITOR
Related Record Type Details
Structure of PRIRALFINAMIDE
ACTIVE MOIETY
NIH
NCATS
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