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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
A5595LHJ2L
Record Status Validated (UNII)
Record Version