Losartan Carboxylic Acid

• CAT Number: R004266
• CAS Number: 124750-92-1
• Molecular Formula: C22H21ClN6O2
• Molecular Weight: 436.9
• Purity: ≥95%
• Target: Angiotensin Receptor
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: 2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid
• InChI: InChI=1S/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
• InChIKey: ZEUXAIYYDDCIRX-UHFFFAOYSA-N
• SMILES: CCCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)C(=O)O)Cl

EXP-3174, also known as Losartan Carboxylic Acid, is a physiologically active metabolite of losartan, produced by cytochrome P450 isoforms in the liver. Like the parent compound, EXP-3174 is a potent AT1 antagonist (Kis = 0.57 and 0.67 nM for rat and human forms, respectively), producing a depressor response and vasodilatation. When administered intravenously, losartan carboxylic acid is more potent and has a longer duration of action than losartan. However, the metabolite has very low oral bioavailability.

Reference

1:Simultaneous Determination and Pharmacokinetic Study of Losartan, Losartan Carboxylic Acid, Ramipril, Ramiprilat, and Hydrochlorothiazide in Rat Plasma by a Liquid Chromatography/Tandem Mass Spectrometry Method. Dubey R, Ghosh M.Sci Pharm. 2014 Nov 30;83(1):107-24. doi: 10.3797/scipharm.1410-15. Print 2015 Jan-Mar. PMID: 26839805 Free PMC Article
2:Simultaneous Determination and Pharmacokinetics of Metolazone, Losartan and Losartan Carboxylic Acid in Rat Plasma by HPLC-ESI-MS-MS. Dubey R, Ghosh M, Sinha BN, Muthukrishnan V.J Chromatogr Sci. 2015 Oct;53(9):1520-7. doi: 10.1093/chromsci/bmv047. Epub 2015 May 6. PMID: 25947361