EXP3174, 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, EXP3174 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.
Chemical Formula: C22H21ClN6O2
Exact Mass: 436.1415
Molecular Weight: 436.9
Elemental Analysis: C, 60.48; H, 4.85; Cl, 8.11; N, 19.24; O, 7.32
Losartan Carboxylic Acid
InChi Code: 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)
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
The specific binding of [125I]-angiotensin II to VSMC is inhibited by EXP3174 with an IC50 of 1.1 nM. Losartan Carboxylic Acid abolishes the angiotensin II-induced formation of inositolphosphates in VSMC.
EXP3174 inhibits the angiotensin II-induced elevation of intracellular cytosolic Ca2+ concentration with an IC50 of 5 nM.
EXP3174 is more effective than losartan in blocking the angiotensin II-induced increase in Egr-1 mRNA.
EXP3174 inhibits the angiotensin II-induced cell protein synthesis with an IC50 of 3 nM.
EXP3174 (0.1 mg/kg; i.v. followed by 0.02 mg/kg/h for 5.5 h) induces a similar level of inhibition (87±4%) of the pressor responses to angiotensin I.
Intravenous EXP3174 (0.1 mg/kg+0.01 mg/kg/min) is infused in anesthetized dogs with recent (8.1±0.4 days) anterior myocardial infarction. Electrolytic injury of the left circumflex coronary artery to induce thrombotic occlusion and posterolateral ischemia is initiated 1 h after the start of treatment.
Choi JS, Choi JS, Choi DH. Effects of licochalcon A on the pharmacokinetics of losartan and its active metabolite,EXP3174, in rats. Pharmazie. 2013 Nov;68(11):882-8. PubMed PMID: 24380237.
Yang SH, Choi JS, Choi DH. Effects of HMG-CoA reductase inhibitors on the pharmacokinetics of losartan and its main metabolite EXP3174 in rats: possible role of CYP3A4 and P-gp inhibition by HMG-CoA reductase inhibitors. Pharmacology. 2011;88(1-2):1-9. doi: 10.1159/000328773. Epub 2011 Jun 25. PubMed PMID: 21709429.
Yang SH, Cho YA, Choi JS. Effects of ticlopidine on pharmacokinetics of losartan and its main metabolite EXP3174 in rats. Acta Pharmacol Sin. 2011 Jul;32(7):967-72. doi: 10.1038/aps.2011.32. Epub 2011 Jun 13. PubMed PMID: 21666702; PubMed Central PMCID: PMC4003123.
Choi DH, Li C, Choi JS. Effects of myricetin, an antioxidant, on the pharmacokinetics of losartan and its active metabolite, EXP3174, in rats: possible role of cytochrome P450 3A4, cytochrome P450 2C9 and P-glycoprotein inhibition by myricetin. J Pharm Pharmacol. 2010 Jul;62(7):908-14. doi: 10.1211/jpp.62.07.0012. PubMed PMID: 20636879.
Kolocouri F, Dotsikas Y, Apostolou C, Kousoulos C, Loukas YL. Simultaneous determination of losartan, EXP3174 and hydrochlorothiazide in plasma via fully automated 96-well-format-based solid-phase extraction and liquid chromatography-negative electrospray tandem mass spectrometry. Anal Bioanal Chem. 2007 Jan;387(2):593-601. Epub 2006 Nov 21. PubMed PMID: 17119933.
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