MedKoo Cat#: 319609 | Name: Lesogaberan

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lesogaberan, 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.

Chemical Structure

Lesogaberan
Lesogaberan
CAS#344413-67-8

Theoretical Analysis

MedKoo Cat#: 319609

Name: Lesogaberan

CAS#: 344413-67-8

Chemical Formula: C3H9FNO2P

Exact Mass: 141.0355

Molecular Weight: 141.08

Elemental Analysis: C, 25.54; H, 6.43; F, 13.47; N, 9.93; O, 22.68; P, 21.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
AZD-3355; AZD 3355; AZD3355; Lesogaberan.
IUPAC/Chemical Name
((R)-3-Amino-2-fluoropropyl)phosphinic acid
InChi Key
LJNUIEQATDYXJH-GSVOUGTGSA-N
InChi Code
InChI=1S/C3H9FNO2P/c4-3(1-5)2-8(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1
SMILES Code
O=P(C[C@H](F)CN)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 141.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Miner PB Jr, Silberg DG, Ruth M, Miller F, Pandolfino J. Dose-dependent effects of lesogaberan on reflux measures in patients with refractory gastroesophageal reflux disease: a randomized, placebo-controlled study. BMC Gastroenterol. 2014 Nov 18;14:188. doi: 10.1186/1471-230X-14-188. PubMed PMID: 25407279; PubMed Central PMCID: PMC4289246. 2: Holmberg AA, Ekdahl A, Weidolf L. Systemic exposure to the metabolites of lesogaberan in humans and animals: a case study of metabolites in safety testing. Drug Metab Dispos. 2014 Jun;42(6):1016-21. doi: 10.1124/dmd.113.056614. Epub 2014 Mar 21. PubMed PMID: 24658456. 3: Dunér K, Bottner P, Norlén AK. Development of analytical methods for the quantification of metabolites of lesogaberan in a MIST investigation. Biomed Chromatogr. 2014 Mar;28(3):362-8. doi: 10.1002/bmc.3029. Epub 2013 Sep 5. PubMed PMID: 24037996. 4: Ekdahl A, Aurell-Holmberg A, Castagnoli N Jr. Identification of the metabolites of lesogaberan using linear trap quadrupole orbitrap mass spectrometry and hydrophilic interaction liquid chromatography. Xenobiotica. 2013 May;43(5):461-7. doi: 10.3109/00498254.2012.725486. Epub 2012 Oct 3. PubMed PMID: 23030741. 5: Canning BJ, Mori N, Lehmann A. Antitussive effects of the peripherally restricted GABAB receptor agonist lesogaberan in guinea pigs: comparison to baclofen and other GABAB receptor-selective agonists. Cough. 2012 Oct 1;8(1):7. doi: 10.1186/1745-9974-8-7. PubMed PMID: 23025757; PubMed Central PMCID: PMC3520872. 6: Shaheen NJ, Denison H, Björck K, Karlsson M, Silberg DG. Efficacy and safety of lesogaberan in gastro-oesophageal reflux disease: a randomised controlled trial. Gut. 2013 Sep;62(9):1248-55. doi: 10.1136/gutjnl-2012-302737. Epub 2012 Jun 23. PubMed PMID: 22730470. 7: Fransson B, Silberg DG, Niazi M, Miller F, Ruth M, Holmberg AA. Effect of food on the bioavailability of lesogaberan given as an oral solution or as modified-release capsules in healthy male volunteers. Int J Clin Pharmacol Ther. 2012 Apr;50(4):307-14. PubMed PMID: 22456303. 8: Boeckxstaens GE, Denison H, Jensen JM, Lehmann A, Ruth M. Translational gastrointestinal pharmacology in the 21st century: 'the lesogaberan story'. Curr Opin Pharmacol. 2011 Dec;11(6):630-3. doi: 10.1016/j.coph.2011.10.011. Epub 2011 Oct 27. Review. PubMed PMID: 22036168. 9: Niazi M, Skrtic S, Ruth M, Holmberg AA. Pharmacokinetic profile of lesogaberan (AZD3355) in healthy subjects: a novel GABA(B)-receptor agonist reflux inhibitor. Drugs R D. 2011;11(1):77-83. doi: 10.2165/11590310-000000000-00000. PubMed PMID: 21410297; PubMed Central PMCID: PMC3585951. 10: Boeckxstaens GE, Beaumont H, Hatlebakk JG, Silberg DG, Björck K, Karlsson M, Denison H. A novel reflux inhibitor lesogaberan (AZD3355) as add-on treatment in patients with GORD with persistent reflux symptoms despite proton pump inhibitor therapy: a randomised placebo-controlled trial. Gut. 2011 Sep;60(9):1182-8. doi: 10.1136/gut.2010.235630. Epub 2011 Mar 14. PubMed PMID: 21402616. 11: Niazi M, Silberg DG, Miller F, Ruth M, Holmberg AA. Evaluation of the pharmacokinetic interaction between lesogaberan (AZD3355) and esomeprazole in healthy subjects. Drugs R D. 2010;10(4):243-51. doi: 10.2165/11588180-000000000-00000. PubMed PMID: 21171670; PubMed Central PMCID: PMC3586101. 12: Falk GW. Inhibition of transient lower esophageal sphincter relaxation in GERD: will lesogaberan advance the field? Gastroenterology. 2010 Aug;139(2):377-9. doi: 10.1053/j.gastro.2010.06.028. Epub 2010 Jun 23. PubMed PMID: 20600061. 13: Boeckxstaens GE, Beaumont H, Mertens V, Denison H, Ruth M, Adler J, Silberg DG, Sifrim D. Effects of lesogaberan on reflux and lower esophageal sphincter function in patients with gastroesophageal reflux disease. Gastroenterology. 2010 Aug;139(2):409-17. doi: 10.1053/j.gastro.2010.04.051. Epub 2010 May 5. PubMed PMID: 20451523. 14: Boeckxstaens GE, Rydholm H, Lei A, Adler J, Ruth M. Effect of lesogaberan, a novel GABA(B)-receptor agonist, on transient lower oesophageal sphincter relaxations in male subjects. Aliment Pharmacol Ther. 2010 Jun;31(11):1208-17. doi: 10.1111/j.1365-2036.2010.04283.x. Epub 2010 Mar 4. PubMed PMID: 20222915. 15: Brändén L, Fredriksson A, Harring E, Jensen J, Lehmann A. The novel, peripherally restricted GABAB receptor agonist lesogaberan (AZD3355) inhibits acid reflux and reduces esophageal acid exposure as measured with 24-h pHmetry in dogs. Eur J Pharmacol. 2010 May 25;634(1-3):138-41. doi: 10.1016/j.ejphar.2010.02.015. Epub 2010 Feb 20. PubMed PMID: 20176012. 16: Bredenoord AJ. Lesogaberan, a GABA(B) agonist for the potential treatment of gastroesophageal reflux disease. IDrugs. 2009 Sep;12(9):576-84. PubMed PMID: 19697277.