MIROGABALIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H19NO2
Molecular Weight	209.2848
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCC1=C[C@@H]2[C@@H](C[C@]2(CN)CC(O)=O)C1

InChI

InChIKey=FTBQORVNHOIASH-CKYFFXLPSA-N

InChI=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

HIDE SMILES / InChI

Molecular Formula	C12H19NO2
Molecular Weight	209.2848
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated calcium channel alpha2/delta subunit 1 19	Binding Agent 1,076		13.5 nM [Kd]
Voltage-gated calcium channel alpha2/delta subunit 2 6	Binding Agent 1,076		22.7 nM [Kd]

C_max

Value	Dose	Analyte	Population
49 ng/mL	3 mg single, oral	MIROGABALIN plasma	Homo sapiens
78 ng/mL	5 mg single, oral	MIROGABALIN plasma	Homo sapiens
205 ng/mL	10 mg single, oral	MIROGABALIN plasma	Homo sapiens
433 ng/mL	30 mg single, oral	MIROGABALIN plasma	Homo sapiens
671 ng/mL	50 mg single, oral	MIROGABALIN plasma	Homo sapiens
1060 ng/mL	75 mg single, oral	MIROGABALIN plasma	Homo sapiens
97 ng/mL	5 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
211 ng/mL	10 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
296 ng/mL	15 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
354 ng/mL	20 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
6050 ng/mL	150 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
184 ng × h/mL	3 mg single, oral	MIROGABALIN plasma	Homo sapiens
276 ng × h/mL	5 mg single, oral	MIROGABALIN plasma	Homo sapiens
614 ng × h/mL	10 mg single, oral	MIROGABALIN plasma	Homo sapiens
1682 ng × h/mL	30 mg single, oral	MIROGABALIN plasma	Homo sapiens
3231 ng × h/mL	50 mg single, oral	MIROGABALIN plasma	Homo sapiens
4896 ng × h/mL	75 mg single, oral	MIROGABALIN plasma	Homo sapiens
406 ng × h/mL	5 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
857 ng × h/mL	10 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
1033 ng × h/mL	15 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
1469 ng × h/mL	20 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
40360 ng × h/mL	150 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.31 h	3 mg single, oral	MIROGABALIN plasma	Homo sapiens
2.96 h	5 mg single, oral	MIROGABALIN plasma	Homo sapiens
3.32 h	10 mg single, oral	MIROGABALIN plasma	Homo sapiens
3.37 h	30 mg single, oral	MIROGABALIN plasma	Homo sapiens
3.82 h	50 mg single, oral	MIROGABALIN plasma	Homo sapiens
4.94 h	75 mg single, oral	MIROGABALIN plasma	Homo sapiens
3.58 h	5 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
4.55 h	10 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
4.23 h	15 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
5.8 h	20 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens
7.06 h	150 mg 2 times / day steady-state, oral	MIROGABALIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
75%	unknown, unknown		MIROGABALIN plasma	Homo sapiens

PubMed

Title	Date	PubMed
No data available in table

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
Record UNII	S7LK2KDM5U
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

A-200-0700

Preferred Name

English

MIROGABALIN

Official Name

English

MIROGABALIN [USAN]

Common Name

English

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

Common Name

English

A200-0700

Code

English

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Code System

Code

Type

Description

INN

9767

PRIMARY

DRUG BANK

DB11825

PRIMARY

USAN

CD-59

PRIMARY

WIKIPEDIA

Mirogabalin

PRIMARY

EPA CompTox

DTXSID001032301

PRIMARY

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					S7LK2KDM5U

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SMILES

InChI

Originator

Approval Year

Targets

Cmax

AUC

T1/2

Funbound

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound