Lesogaberan

• CAT Number: I007645
• CAS Number: 344413-67-8
• Molecular Formula: C3H8FNO2P+
• Molecular Weight: 140.074
• Purity: ≥95%
• Target: reflux inhibitor
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term , or -20°C for long term.
• IUPAC Name: [(2R)-3-amino-2-fluoropropyl]-hydroxy-oxophosphanium
• InChI: InChI=1S/C3H7FNO2P/c4-3(1-5)2-8(6)7/h3H,1-2,5H2/p+1/t3-/m1/s1
• InChIKey: WVTGPBOMAQLPCP-GSVOUGTGSA-O
• SMILES: C(C(C[P+](=O)O)F)N

Lesogaberan (Cat.No:I007645), also known as AZD-3355, is a potent and selective reflux inhibitor developed by AstraZeneca for the treatment of gastroesophageal reflux disease (GERD). As a GABAB receptor agonist, it has the same mechanism of action as baclofen, but is anticipated to have fewer of the central nervous system side effects that limit the clinical use of baclofen for the treatment of GERD.

Reference

1:Reducing Adverse Effects During Drug Development: The Example of Lesogaberan and Paresthesia. Rydholm H, von Corswant C, Denison H, Jensen JM, Lehmann A, Ruth M, Söderlind E, Aurell-Holmberg A.Clin Ther. 2016 Apr;38(4):946-60. doi: 10.1016/j.clinthera.2016.02.012. Review. PMID: 26947796 2:Dose-dependent effects of lesogaberan on reflux measures in patients with refractory gastroesophageal reflux disease: a randomized, placebo-controlled study. Miner PB Jr, Silberg DG, Ruth M, Miller F, Pandolfino J.BMC Gastroenterol. 2014 Nov 18;14:188. doi: 10.1186/1471-230X-14-188. PMID: 25407279 Free PMC Article3:Systemic exposure to the metabolites of lesogaberan in humans and animals: a case study of metabolites in safety testing. Holmberg AA, Ekdahl A, Weidolf L.Drug Metab Dispos. 2014 Jun;42(6):1016-21. doi: 10.1124/dmd.113.056614. Epub 2014 Mar 21. PMID: 24658456 Free Article4:Development of analytical methods for the quantification of metabolites of lesogaberan in a MIST investigation. Dunér K, Bottner P, Norlén AK.Biomed Chromatogr. 2014 Mar;28(3):362-8. doi: 10.1002/bmc.3029. Epub 2013 Sep 5. PMID: 24037996 5:Identification of the metabolites of lesogaberan using linear trap quadrupole orbitrap mass spectrometry and hydrophilic interaction liquid chromatography. Ekdahl A, Aurell-Holmberg A, Castagnoli N Jr.Xenobiotica. 2013 May;43(5):461-7. doi: 10.3109/00498254.2012.725486. Epub 2012 Oct 3. PMID: 23030741 6:Antitussive effects of the peripherally restricted GABAB receptor agonist lesogaberan in guinea pigs: comparison to baclofen and other GABAB receptor-selective agonists. Canning BJ, Mori N, Lehmann A.Cough. 2012 Oct 1;8(1):7. doi: 10.1186/1745-9974-8-7. PMID: 23025757 Free PMC Article7:Efficacy and safety of lesogaberan in gastro-oesophageal reflux disease: a randomised controlled trial. Shaheen NJ, Denison H, Björck K, Karlsson M, Silberg DG.Gut. 2013 Sep;62(9):1248-55. doi: 10.1136/gutjnl-2012-302737. Epub 2012 Jun 23. PMID: 22730470 8:Effect of food on the bioavailability of lesogaberan given as an oral solution or as modified-release capsules in healthy male volunteers. Fransson B, Silberg DG, Niazi M, Miller F, Ruth M, Holmberg AA.Int J Clin Pharmacol Ther. 2012 Apr;50(4):307-14. PMID: 22456303 9:Translational gastrointestinal pharmacology in the 21st century: /’the lesogaberan story/’. Boeckxstaens GE, Denison H, Jensen JM, Lehmann A, Ruth M.Curr Opin Pharmacol. 2011 Dec;11(6):630-3. doi: 10.1016/j.coph.2011.10.011. Epub 2011 Oct 27. Review. PMID: 22036168 10:Pharmacokinetic profile of lesogaberan (AZD3355) in healthy subjects: a novel GABA(B)-receptor agonist reflux inhibitor. Niazi M, Skrtic S, Ruth M, Holmberg AA.Drugs R D. 2011;11(1):77-83. doi: 10.2165/11590310-000000000-00000. PMID: 21410297 Free PMC Article