MIROGABALIN BESYLATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H19NO2.C6H6O3S
Molecular Weight	367.46
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.CCC2=C[C@@H]3[C@@H](C[C@]3(CN)CC(O)=O)C2

InChI

InChIKey=OKJXJRVWXYRSAN-TXULWXBWSA-N

InChI=1S/C12H19NO2.C6H6O3S/c1-2-8-3-9-5-12(7-13,6-11(14)15)10(9)4-8;7-10(8,9)6-4-2-1-3-5-6/h4,9-10H,2-3,5-7,13H2,1H3,(H,14,15);1-5H,(H,7,8,9)/t9-,10-,12-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C12H19NO2
Molecular Weight	209.2848
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C6H6O3S
Molecular Weight	158.175
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30672128 | https://www.ncbi.nlm.nih.gov/pubmed/30913164 | https://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/006800.html

Mirogabalin, a selective alpha 2 delta ligand binds to the α2δ subunits of voltage-dependent calcium channels and thus blocks the channel. This drug was developed by Daiichi Sankyo and in January 2019 was approved in Japan for the treatment of neuropathic pain and for the postherpetic neuralgia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated calcium channel alpha2/delta subunit 1 19 Target ID: CHEMBL1919 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29563324	Binding Agent 1076		13.5 nM [Kd]
Voltage-gated calcium channel alpha2/delta subunit 2 6 Target ID: CHEMBL3896 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29563324	Binding Agent 1076		22.7 nM [Kd]

C_max

Value	Dose	Analyte	Population
49 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
78 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
205 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
433 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
671 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1060 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
97 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
211 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
296 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	15 mg 2 times / day steady-state, oral dose: 15 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
354 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6050 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
184 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
276 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
614 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1682 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3231 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4896 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
406 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
857 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1033 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	15 mg 2 times / day steady-state, oral dose: 15 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1469 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
40360 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.82 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.58 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	15 mg 2 times / day steady-state, oral dose: 15 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30151212/	150 mg 2 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	MIROGABALIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
75% REVIEW https://pubmed.ncbi.nlm.nih.gov/33380563/	unknown, unknown		MIROGABALIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
The antibiotic, L-beta-(5-hydroxy-2-pyridyl)-alanine specifically inhibits growth of the NIH3T3 cells transformed by activated human c-Ha-ras and induces formation of flat revertant cells.	1988	3067212
Mirogabalin for the management of postherpetic neuralgia: a randomized, double-blind, placebo-controlled phase 3 study in Asian patients.	2019 May	30913164

Patents

Sample Use Guides

In Vivo Use Guide

postherpetic neuralgia: mirogabalin 15, 20, or 30 mg/day for up to 14 weeks peripheral neuropathic pain: mirogabalin 30 mg/day showed statistically significant pain relief

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:36:30 GMT 2025` Edited by `admin` on `Mon Mar 31 22:36:30 GMT 2025`
Record UNII	01F4FRP8YL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIROGABALIN BESYLATE [USAN]

Preferred Name

English

MIROGABALIN BESYLATE

Official Name

English

BICYCLO(3.2.0)HEPT-3-ENE-6-ACETIC ACID, 6-(AMINOMETHYL)-3-ETHYL-, (1R,5S,6S)-, BENZENESULFONATE (1:1)

Systematic Name

English

Mirogabalin besilate [WHO-DD]

Common Name

English

[(1R,5S,6S)-6-(Aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid monobenzenesulfonate

Systematic Name

English

MIROGABALIN BESILATE [JAN]

Common Name

English

DS5565

Code

English

Mirogabalin besilate

Common Name

English

DS-5565

Code

English

Code System Code Type Description

USAN

CD-60