OLSALAZINE

• CAT Number: M083664
• CAS Number: 15722-48-2
• Molecular Formula: C14H10N2O6
• Molecular Weight: 302.242
• Purity: ≥95%
• Storage: Store at -20C
• IUPAC Name: 5-[(2Z)-2-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-2-hydroxybenzoic acid
• InChI: InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,15,17H,(H,19,20)(H,21,22)/b16-8-
• InChIKey: ULGVHUUBIHTFAM-PXNMLYILSA-N
• SMILES: C1=CC(=C(C=C1NN=C2C=CC(=O)C(=C2)C(=O)O)C(=O)O)O

Olsalazine is an anti-inflammatory drug used in the treatment of inflammatory bowel disease such as ulcerative colitis. Like balsalazide, olsalazine is believed to deliver mesalazine, or 5-aminosalicylic acid (5-ASA), past the small intestine, directly to the large intestine, which is the active site of disease in ulcerative colitis.

Reference

1:Olsalazine-Based Metal-Organic Frameworks as Biocompatible Platforms for H2 Adsorption and Drug Delivery. Levine DJ, Runčevski T, Kapelewski MT, Keitz BK, Oktawiec J, Reed DA, Mason JA, Jiang HZ, Colwell KA, Legendre CM, FitzGerald SA, Long JR.J Am Chem Soc. 2016 Aug 17;138(32):10143-50. doi: 10.1021/jacs.6b03523. Epub 2016 Aug 3. PMID: 27486905 2:Determination of mesalazine, a low bioavailability olsalazine metabolite in human plasma by UHPLC-MS/MS: Application to a pharmacokinetic study. Banda J, Lakshmanan R, Katepalli RB, Reddy Venati UK, Koppula R, Shiva Prasad VV.J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jan 1;1008:1-10. doi: 10.1016/j.jchromb.2015.11.001. Epub 2015 Nov 4. PMID: 26606108 3:Technetium-99 m labeling and evaluation of olsalazine: a novel agent for ulcerative colitis imaging. El-Kawy OA, Ibrahim IT, Farah K.J Labelled Comp Radiopharm. 2015 Jun 30;58(8):336-41. doi: 10.1002/jlcr.3306. Epub 2015 Jun 1. PMID: 26031480 4:Toward drug repurposing in epigenetics: olsalazine as a hypomethylating compound active in a cellular context. Méndez-Lucio O, Tran J, Medina-Franco JL, Meurice N, Muller M.ChemMedChem. 2014 Mar;9(3):560-5. doi: 10.1002/cmdc.201300555. Epub 2014 Jan 31. PMID: 24482360 5:Thrombocytopenia associated with 5-aminosalicylate prodrug, olsalazine: is the devil still there? Rao Y, Zheng F.Int J Clin Pharm. 2013 Aug;35(4):529-31. doi: 10.1007/s11096-013-9778-8. Epub 2013 Apr 27. PMID: 23625279 6:Degradation kinetics of metronidazole and olsalazine by bacteria in ascending colon and in feces of healthy adults. Vertzoni M, Carlsson A, Abrahamsson B, Goumas K, Reppas C.Int J Pharm. 2011 Jul 15;413(1-2):81-6. doi: 10.1016/j.ijpharm.2011.04.028. Epub 2011 Apr 22. PMID: 21540091 7:Molecular nanofibers of olsalazine form supramolecular hydrogels for reductive release of an anti-inflammatory agent. Li X, Li J, Gao Y, Kuang Y, Shi J, Xu B.J Am Chem Soc. 2010 Dec 22;132(50):17707-9. doi: 10.1021/ja109269v. Epub 2010 Dec 1. PMID: 21121607 Free PMC Article8:An experimental study on ulcerative colitis as a potential target for probiotic therapy by Lactobacillus acidophilus with or without /olsalazine/. Abdin AA, Saeid EM.J Crohns Colitis. 2008 Dec;2(4):296-303. doi: 10.1016/j.crohns.2008.04.002. Epub 2008 Jun 26. PMID: 21172227 9:Efficacy and tolerability of olsalazine (dipentum) in the treatment of patients with ulcerative colitis–results of a field study. Singer MV, Schmausser H, Schönfeld G.Hepatogastroenterology. 2006 May-Jun;53(69):317-21. PMID: 16795963 10:Comparative analysis of the in vitro prosecretory effects of balsalazide, sulfasalazine, olsalazine, and mesalamine in rabbit distal ileum. Kles KA, Vavricka SR, Turner JR, Musch MW, Hanauer SB, Chang EB.Inflamm Bowel Dis. 2005 Mar;11(3):253-7. PMID: 15735431