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Chemistry

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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
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 Weight 806.0 g/mol
Molecular Formula C38H51N3O12S2
XLogP33.1
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count13
Rotatable Bond Count14
Exact Mass805.29141642 g/mol
Monoisotopic Mass805.29141642 g/mol
Topological Polar Surface Area238 Ų
Heavy Atom Count55
Formal Charge0
Complexity1450
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


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ABOUT THIS PAGE

Volixibat Manufacturers

A Volixibat manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Volixibat, including repackagers and relabelers. The FDA regulates Volixibat manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Volixibat API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Volixibat Suppliers

A Volixibat supplier is an individual or a company that provides Volixibat active pharmaceutical ingredient (API) or Volixibat finished formulations upon request. The Volixibat suppliers may include Volixibat API manufacturers, exporters, distributors and traders.

Volixibat GMP

Volixibat Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Volixibat GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Volixibat GMP manufacturer or Volixibat GMP API supplier for your needs.

Volixibat CoA

A Volixibat CoA (Certificate of Analysis) is a formal document that attests to Volixibat's compliance with Volixibat specifications and serves as a tool for batch-level quality control.

Volixibat CoA mostly includes findings from lab analyses of a specific batch. For each Volixibat CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Volixibat may be tested according to a variety of international standards, such as European Pharmacopoeia (Volixibat EP), Volixibat JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Volixibat USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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