elobixibat   Click here for help

GtoPdb Ligand ID: 9996

Synonyms: 2-[[(2R)-2-[[2-[(3,3-dibutyl-7-methylsulfanyl-1,1-dioxo-5-phenyl-2,4-dihydro-1λ6,5-benzothiazepin-8-yl)oxy]acetyl]amino]-2-phenylacetyl]amino]acetic acid | A3309 | AJG533 | AZD-7806 | AZD7806 | Goofice®
Approved drug
elobixibat is an approved drug (Japan (2018))
Compound class: Synthetic organic
Comment: Elobixibat is an orally available inhibitor of the ileal bile acid transporter (IBAT or ASBT), which is the protein product of the SLC10A2 gene. It is being evaluated for clinical utility in the management of chronic constipation [1,3,6]. The chemical structure is claimed as Example 14 in Albireo Ab's patent US20130225511A1 [2] (we have chosen this iteration of the patent as it has both chemical structure images and data included in online versions).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 18
Topological polar surface area 175.79
Molecular weight 695.27
XLogP 7.58
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCC1(CCCC)CN(c2ccccc2)c2c(S(=O)(=O)C1)cc(c(c2)SC)OCC(=O)NC(c1ccccc1)C(=O)NCC(=O)O
Isomeric SMILES CCCCC1(CCCC)CN(c2ccccc2)c2c(S(=O)(=O)C1)cc(c(c2)SC)OCC(=O)N[C@H](c1ccccc1)C(=O)NCC(=O)O
InChI InChI=1S/C36H45N3O7S2/c1-4-6-18-36(19-7-5-2)24-39(27-16-12-9-13-17-27)28-20-30(47-3)29(21-31(28)48(44,45)25-36)46-23-32(40)38-34(26-14-10-8-11-15-26)35(43)37-22-33(41)42/h8-17,20-21,34H,4-7,18-19,22-25H2,1-3H3,(H,37,43)(H,38,40)(H,41,42)/t34-/m1/s1
InChI Key XFLQIRAKKLNXRQ-UUWRZZSWSA-N
References
1. Acosta A, Camilleri M. (2014)
Elobixibat and its potential role in chronic idiopathic constipation.
Therap Adv Gastroenterol, 7 (4): 167-75. [PMID:25057297]
2. Gillberg P-G, Graffner H, Starke I. (2013)
Ibat inhibitors for the treatment of liver diseases.
Patent number: US20130225511A1. Assignee: Albireo AB. Priority date: 08/11/2010. Publication date: 29/08/2013.
3. Mosińska P, Fichna J, Storr M. (2015)
Inhibition of ileal bile acid transporter: An emerging therapeutic strategy for chronic idiopathic constipation.
World J. Gastroenterol., 21 (24): 7436-42. [PMID:26139989]
4. Nakajima A, Seki M, Taniguchi S, Ohta A, Gillberg PG, Mattsson JP, Camilleri M. (2018)
Safety and efficacy of elobixibat for chronic constipation: results from a randomised, double-blind, placebo-controlled, phase 3 trial and an open-label, single-arm, phase 3 trial.
Lancet Gastroenterol Hepatol, 3 (8): 537-547. [PMID:29805116]
5. Nakajima A, Taniguchi S, Kurosu S, Gillberg PG, Mattsson JP, Camilleri M. (2019)
Efficacy, long-term safety, and impact on quality of life of elobixibat in more severe constipation: Post hoc analyses of two phase 3 trials in Japan.
Neurogastroenterol. Motil., 31 (5): e13571. [PMID:30793431]
6. Wong BS, Camilleri M. (2013)
Elobixibat for the treatment of constipation.
Expert Opin Investig Drugs, 22 (2): 277-84. [PMID:23215781]