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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H14F3NO5
Molecular Weight 429.3455
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FUNAPIDE

SMILES

FC(F)(F)C1=CC=C(CN2C(=O)[C@@]3(COC4=CC5=C(OCO5)C=C34)C6=CC=CC=C26)O1

InChI

InChIKey=NEBUOXBYNAHKFV-NRFANRHFSA-N
InChI=1S/C22H14F3NO5/c23-22(24,25)19-6-5-12(31-19)9-26-15-4-2-1-3-13(15)21(20(26)27)10-28-16-8-18-17(7-14(16)21)29-11-30-18/h1-8H,9-11H2/t21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H14F3NO5
Molecular Weight 429.3455
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Funapide (also known as TV 45070; XEN 402) is a small molecule blocker of the voltage-gated sodium channels Nav1.7 (SCN9A) and Nav1.8. Funapide was developed as a potential treatment of pain conditions, including osteoarthritis, neuropathic pain, postherpetic neuralgia, and erythromelalgia, as well as dental pain. In April 2013, the US FDA granted orphan drug designation to funapide for the treatment of pain associated with erythromelalgia (EM). EM is a rare autosomal dominant condition characterized by debilitating spontaneous or easily evoked attacks of symmetrical burning pain in the feet and hands, typically associated with elevated skin temperature and erythema (redness of the skin). Funapide also was involved in phase II clinical trials in patients with post herpetic neuralgia and in participants with primary osteoarthritis (OA) affecting a single knee. On March 7, 2018, Teva Pharmaceutical and Xenon Pharmaceuticals entered into a mutual agreement to terminate the collaborative development and license agreement they entered into in 2012 for the pain drug funapide. The reason was that the top line results of funapide phase 2 study in post-herpetic neuralgia patients failed to meet the primary or secondary endpoints.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q15858|||Q8WWN4
Gene ID: 6335.0
Gene Symbol: SCN9A
Target Organism: Homo sapiens (Human)
Target ID: Q9Y5Y9
Gene ID: 6336.0
Gene Symbol: SCN10A
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Blockade of the PD-1/PD-1L pathway reverses the protective effect of anti-CD40L therapy in a rat to mouse concordant islet xenotransplantation model.
2007 May
Recent progress in sodium channel modulators for pain.
2014 Aug 15
Patents

Patents

Sample Use Guides

TV-45070 (FUNAPIDE) ointment in a 4% strength applied topically twice daily to the area of postherpetic neuralgia (PHN) pain during the treatment period from days 1 through 28
Route of Administration: Topical
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:37 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:37 GMT 2023
Record UNII
A5595LHJ2L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FUNAPIDE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
TV-45070
Code English
XPF-002
Code English
FUNAPIDE [USAN]
Common Name English
(3'S)-1'-((5-(TRIFLUOROMETHYL)FURAN-2-YL)METHYL)-2H,6H-SPIRO(FURO(2,3-F)(1,3)BENZODIOXOLE-7,3'-INDOL)-2'(1'H)-ONE
Systematic Name English
SPIRO(FURO(2,3-F)-1,3-BENZODIOXOLE-7(6H),3'-(3H)INDOL)-2'(1'H)-ONE, 1'-((5-(TRIFLUOROMETHYL)-2-FURANYL)METHYL)-, (3'S)-
Systematic Name English
Funapide [WHO-DD]
Common Name English
XEN402
Code English
XEN-401-S
Code English
XEN-402
Code English
FUNAPIDE, (+)-
Common Name English
funapide [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 378012
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
Code System Code Type Description
FDA UNII
A5595LHJ2L
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
NCI_THESAURUS
C174600
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
DRUG BANK
DB11769
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
WIKIPEDIA
FUNAPIDE
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
INN
9958
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL3707218
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID201031866
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
PUBCHEM
49836093
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
CAS
1259933-16-8
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
SMS_ID
300000034252
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
USAN
DE-70
Created by admin on Fri Dec 15 16:20:37 GMT 2023 , Edited by admin on Fri Dec 15 16:20:37 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
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ACTIVE MOIETY