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Volixibat

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Also known as: 1025216-57-2, Sar-548304 free acid, X2jz0451h8, N-(3-o-benzyl-6-o-sulfo-beta-d-glucopyranosyl)-n'-{3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1h-1lambda6-benzothiepin-5-yl]phenyl}urea, Volixibat [usan:inn], Unii-x2jz0451h8

Molecular Formula

C₃₈H₅₁N₃O₁₂S₂

Molecular Weight

806.0 g/mol

InChI Key

ULVBLFBUTQMAGZ-RTNCXNSASA-N

FDA UNII

X2JZ0451H8

Volixibat, also known as SHP626 or LUM002, is an investigational drug that will potentially be used for the treatment of Non-Alcoholic Steatohepatitis (NASH). If approved for use, it will be the first available agent for the treatment of NASH. Volixibat is a selective inhibitor of the apical sodium-dependent bile acid transporter (ASBT), a transmembrane protein primarily expressed by enterocytes of the ileum. Also known as the ileal bile acid transporter (IBAT), ASBT is primarily responsible for the enterohepatic recirculation of bile acids and ultimately for hepatic lipid and glucose metabolism. Inhibiting this enzyme results in a decrease of bile acids returning to the liver, which is helpful for the treatment of NASH as abnormal cholesterol metabolism and accumulation of free cholesterol in the liver have been implicated in its pathogenesis. According to Shire, the pharmaceutical manufacturer of Volixibat, it has been granted fast track status by the Food and Drug Administration due to promising initial results and a need for therapeutic treatments for NASH.

1 2D Structure

Volixibat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R,4S,5R,6R)-6-[[3-[(3S,4R,5R)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-4,5-dihydro-2H-16-benzothiepin-5-yl]phenyl]carbamoylamino]-3,5-dihydroxy-4-phenylmethoxyoxan-2-yl]methyl hydrogen sulfate

2.1.2 InChI

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

2.1.3 InChI Key

ULVBLFBUTQMAGZ-RTNCXNSASA-N

2.1.4 Canonical SMILES

CCCCC1(CS(=O)(=O)C2=C(C=C(C=C2)N(C)C)C(C1O)C3=CC(=CC=C3)NC(=O)NC4C(C(C(C(O4)COS(=O)(=O)O)O)OCC5=CC=CC=C5)O)CC

2.1.5 Isomeric SMILES

CCCC[C@@]1(CS(=O)(=O)C2=C(C=C(C=C2)N(C)C)[C@H]([C@H]1O)C3=CC(=CC=C3)NC(=O)N[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COS(=O)(=O)O)O)OCC5=CC=CC=C5)O)CC

2.2 Other Identifiers

2.2.1 UNII

X2JZ0451H8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lum002

2. Shp626

2.3.2 Depositor-Supplied Synonyms

1. 1025216-57-2

2. Sar-548304 Free Acid

3. X2jz0451h8

4. N-(3-o-benzyl-6-o-sulfo-beta-d-glucopyranosyl)-n'-{3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1h-1lambda6-benzothiepin-5-yl]phenyl}urea

5. Volixibat [usan:inn]

6. Unii-x2jz0451h8

7. Starbld0000127

8. Volixibat [inn]

9. Volixibat [usan]

10. Volixibat [who-dd]

11. Chembl3707222

12. Schembl12196537

13. Dtxsid001098929

14. Db13914

15. 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)-

16. Hy-101190

17. Cs-0020958

18. Q27293432

19. [(2r,3r,4s,5r,6r)-6-[[3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-4,5-dihydro-2h-1lambda6-benzothiepin-5-yl]phenyl]carbamoylamino]-3,5-dihydroxy-4-phenylmethoxyoxan-2-yl]methyl Hydrogen Sulfate

20. 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]urea

21. 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)-

2.4 Create Date

2008-10-27

3 Chemical and Physical Properties

Molecular Formula	C₃₈H₅₁N₃O₁₂S₂
Molecular Weight	806.0 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	14
Exact Mass	805.29141642 g/mol
Monoisotopic Mass	805.29141642 g/mol
Topological Polar Surface Area	238 Å²
Heavy Atom Count	55
Formal Charge	0
Complexity	1450
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Volixibat is an investigational drug that has not been approved for use in any conditions.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Lipid Regulating Agents

Substances that alter the metabolism of LIPIDS. (See all compounds classified as Lipid Regulating Agents.)

5.2 Mechanism of Action

Volixibat is a selective inhibitor of the apical sodium-dependent bile acid transporter (ASBT), a transmembrane protein primarily expressed by enterocytes of the ileum. ASBT is primarily responsible for the recirculation of bile acids and therefore for hepatic lipid and glucose metabolism. Inhibiting this enzyme results in a decrease of bile acids returning to the liver, which is helpful for the treatment of NASH as abnormal cholesterol metabolism and accumulation of free cholesterol in the liver have been implicated in its pathogenesis.

Drugs in Development