VOLIXIBAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H51N3O12S2
Molecular Weight	805.954
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC[C@]1(CC)CS(=O)(=O)C2=CC=C(C=C2[C@H]([C@H]1O)C3=CC(NC(=O)N[C@@H]4O[C@H](COS(O)(=O)=O)[C@@H](O)[C@H](OCC5=CC=CC=C5)[C@H]4O)=CC=C3)N(C)C

InChI

InChIKey=ULVBLFBUTQMAGZ-RTNCXNSASA-N

InChI=1S/C38H51N3O12S2/c1-5-7-18-38(6-2)23-54(46,47)30-17-16-27(41(3)4)20-28(30)31(35(38)44)25-14-11-15-26(19-25)39-37(45)40-36-33(43)34(51-21-24-12-9-8-10-13-24)32(42)29(53-36)22-52-55(48,49)50/h8-17,19-20,29,31-36,42-44H,5-7,18,21-23H2,1-4H3,(H2,39,40,45)(H,48,49,50)/t29-,31-,32-,33-,34+,35-,36-,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C38H51N3O12S2
Molecular Weight	805.954
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02787304 | https://www.ncbi.nlm.nih.gov/pubmed/29304731

Volixibat (SHP626; formerly LUM002) is a potent inhibitor of the apical sodium-dependent bile acid transporter (ASBT) that was developed for the treatment of nonalcoholic steatohepatitis. Volixibat participated in phase II clinical trial to investigate its safety, effectiveness in adults with nonalcoholic steatohepatitis. However, this study was discontinued, without any further explanation for the possible causes. In addition, volixibat was studied in a clinical trial in healthy adults and in patients with type 2 diabetes mellitus, where was shown that the drug was generally well tolerated.

Approval Year

PubMed

Title	Date	PubMed
Absorption, Distribution, Metabolism, and Excretion of [(14)C]-Volixibat in Healthy Men: Phase 1 Open-Label Study.	2018 Feb	28702877
Safety, tolerability and pharmacodynamics of apical sodium-dependent bile acid transporter inhibition with volixibat in healthy adults and patients with type 2 diabetes mellitus: a randomised placebo-controlled trial.	2018 Jan 5	29304731
A randomised, double-blind, placebo-controlled phase 1 study of the safety, tolerability and pharmacodynamics of volixibat in overweight and obese but otherwise healthy adults: implications for treatment of non-alcoholic steatohepatitis.	2018 Mar 16	29548345

Patents

Sample Use Guides

In Vivo Use Guide

5 mg, 10 mg, and 20 mg of SHP626 (Volixibat) capsule by orally once daily in a double-blinded fashion

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:46:49 GMT 2023` Edited by `admin` on `Sat Dec 16 09:46:49 GMT 2023`
Record UNII	X2JZ0451H8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VOLIXIBAT

Official Name

English

volixibat [INN]

Common Name

English

SAR-548304 FREE ACID

Code

English

UREA, N-(3-((3S,4R,5R)-3-BUTYL-7-(DIMETHYLAMINO)-3-ETHYL-2,3,4,5-TETRAHYDRO-4-HYDROXY-1,1-DIOXIDO-1-BENZOTHIEPIN-5-YL)PHENYL)-N'-(3-O-(PHENYLMETHYL)-6-O-SULFO-.BETA.-D-GLUCOPYRANOSYL)-

Systematic Name

English

VOLIXIBAT [USAN]

Common Name

English

Volixibat [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78276