mirogabalin

{{Short description|Chemical compound}}

{{Use dmy dates|date=January 2020}}

{{Drugbox

| image = Mirogabalin.svg

| image_class = skin-invert-image

| width = 150

| image2 = Mirogabalin 3D structure.png

| image_class2 = skin-invert-image

| tradename = Tarlige

| pregnancy_AU =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth

| class =

| ATCvet =

| ATC_prefix = N02

| ATC_suffix = BF03

| ATC_supplemental =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 1138245-13-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S7LK2KDM5U

| PubChem = 49802951

| ChemSpiderID = 32701007

| KEGG = D11203

| synonyms = DS-5565

| IUPAC_name = (1R,5S,6S)-6-(aminomethyl)-3-ethyl-bicyclo(3.2.0)hept-3-ene-6-acetic acid

| C = 12

| H = 19

| N = 1

| O = 2

| SMILES = CCC1=CC2C(C1)C[C@@]2(CN)CC(=O)O

| StdInChI = 1S/C12H19NO2/c1-2-8-3-9-5-12(7-13,6-11(14)15)10(9)4-8/h4,9-10H,2-3,5-7,13H2,1H3,(H,14,15)/t9-,10-,12-/m1/s1

| StdInChIKey = FTBQORVNHOIASH-CKYFFXLPSA-N

}}

Mirogabalin (brand name Tarlige; developmental code name DS-5565) is a gabapentinoid medication developed by Daiichi Sankyo. Gabapentin and pregabalin are also members of this class. As a gabapentinoid, mirogabalin binds to the α₂δ subunit of voltage-gated calcium channel (1 and 2), but with significantly higher potency than pregabalin. It has shown promising results in Phase II clinical trials for the treatment of diabetic peripheral neuropathic pain.{{cite journal | vauthors = Vinik A, Rosenstock J, Sharma U, Feins K, Hsu C, Merante D | title = Efficacy and safety of mirogabalin (DS-5565) for the treatment of diabetic peripheral neuropathic pain: a randomized, double-blind, placebo- and active comparator-controlled, adaptive proof-of-concept phase 2 study | journal = Diabetes Care | volume = 37 | issue = 12 | pages = 3253–61 | date = December 2014 | pmid = 25231896 | doi = 10.2337/dc14-1044 | doi-access = free }}{{cite journal | vauthors = Vinik A, Sharma U, Feins K, Hsu C, Merante D | year = 2014 | title = DS-5565 for the Treatment Of Diabetic Peripheral Neuropathic Pain: Randomized, Double-Blind, Placebo- And Active Comparator-Controlled Phase II Study (S20.004) | url = http://www.neurology.org/content/82/10_Supplement/S20.004 | journal = Neurology | volume = 82 | issue = 10| page = S20.004 }}

Phase III trial results:

• Effective: for post-herpetic neuralgia (trial: NEUCOURSE)
• Ineffective: for fibromyalgia (trial: ALDAY){{cite web|url=https://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006653.html|title=Daiichi Sankyo Announces Top-line Results from Phase 3 Global Clinical Development Program Evaluating Mirogabalin in Pain Syndromes|publisher=Daiichi Sankyo |date=30 June 2017}}
• Effective: for diabetic peripheral neuropathic pain (trial: REDUCER){{cite web|url=https://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006706.html|title=Daiichi Sankyo Announces Positive Top-line Results from Phase 3 Clinical Trial Evaluating Mirogabalin in Diabetic Peripheral Neuropathic Pain|publisher=Daiichi Sankyo |date=31 August 2017}}

In Japan, the company submitted a marketing application for treatment of peripheral neuropathic pain.{{cite web|url=https://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006800.html |title=Daiichi Sankyo Submits Marketing Application for Mirogabalin in Japan |publisher=Daiichi Sankyo |date=15 February 2018}} The medication was approved for neuropathic pain and postherpetic neuralgia in Japan in January 2019.{{Cite web|url=https://adisinsight.springer.com/drugs/800033181|title=Mirogabalin - Daiichi Sankyo Company - AdisInsight}}