EXP-3174
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MedKoo CAT#: 522575

CAS#: 124750-92-1

Description: 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.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 60 2 weeks
10mg USD 70 2 weeks
25mg USD 90 2 weeks
50mg USD 150 2 weeks
100mg USD 250 2 weeks
200mg USD 450 2 weeks
500mg USD 750 2 weeks
1g USD 1250 2 weeks
2g USD 2150 2 weeks
5g USD 3950 2 weeks
10g USD 5950 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

EXP-3174, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522575
Name: EXP-3174
CAS#: 124750-92-1
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


Synonym: EXP-3174; EXP 3174; EXP3174; E-3174; E 3174; E3174; Losartan Carboxylic Acid.

IUPAC/Chemical Name: 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid

InChi Key: ZEUXAIYYDDCIRX-UHFFFAOYSA-N

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)

SMILES Code: [H]N1N=NN=C1C2=CC=CC=C2C3=CC=C(CN4C(C(O)=O)=C(Cl)N=C4CCCC)C=C3


Technical Data

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


References

1: Choi JS, Choi JS, Choi DH. Effects of licochalcon A on the pharmacokinetics of losartan and its active metabolite, EXP-3174, in rats. Pharmazie. 2013 Nov;68(11):882-8. PubMed PMID: 24380237.

2: Yang SH, Choi JS, Choi DH. Effects of HMG-CoA reductase inhibitors on the pharmacokinetics of losartan and its main metabolite EXP-3174 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.

3: Yang SH, Cho YA, Choi JS. Effects of ticlopidine on pharmacokinetics of losartan and its main metabolite EXP-3174 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.

4: Choi DH, Li C, Choi JS. Effects of myricetin, an antioxidant, on the pharmacokinetics of losartan and its active metabolite, EXP-3174, 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.

5: Kolocouri F, Dotsikas Y, Apostolou C, Kousoulos C, Loukas YL. Simultaneous determination of losartan, EXP-3174 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.

6: Soldner A, Benet LZ, Mutschler E, Christians U. Active transport of the angiotensin-II antagonist losartan and its main metabolite EXP 3174 across MDCK-MDR1 and caco-2 cell monolayers. Br J Pharmacol. 2000 Mar;129(6):1235-43. PubMed PMID: 10725273; PubMed Central PMCID: PMC1571937.

7: Iwasa T, Takano T, Hara K, Kamei T. Method for the simultaneous determination of losartan and its major metabolite, EXP-3174, in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):325-30. PubMed PMID: 10595730.

8: Soldner A, Spahn-Langguth H, Mutschler E. HPLC assays to simultaneously determine the angiotensin-AT1 antagonist losartan as well as its main and active metabolite EXP 3174 in biological material of humans and rats. J Pharm Biomed Anal. 1998 Jan;16(5):863-73. PubMed PMID: 9535198.

9: Schwarz ER, Montino H, Fleischhauer J, Klues HG, vom Dahl J, Hanrath P. Angiotensin II receptor antagonist EXP 3174 reduces infarct size comparable with enalaprilat and augments preconditioning in the pig heart. Cardiovasc Drugs Ther. 1997 Nov;11(5):687-95. PubMed PMID: 9493708.

10: Heller J, Kramer HJ, Horácek V. Comparative effects of the angiotensin II receptor blocker EXP 3174 and of the angiotensin-converting enzyme inhibitor captopril on renal glomerular hemodynamics in the dog. Kidney Blood Press Res. 1997;20(6):391-7. PubMed PMID: 9453450.

11: Heller J, Horácek V. Effect of PD 123319, an AT-2 antagonist, on renal function of the anesthetized dog: comparison with EXP 3174, an AT-1 blocker. Kidney Blood Press Res. 1997;20(5):297-301. PubMed PMID: 9419044.

12: Li XC, Widdop RE. Angiotensin type 1 receptor antagonists CV-11974 and EXP 3174 cause selective renal vasodilatation in conscious spontaneously hypertensive rats. Clin Sci (Lond). 1996 Aug;91(2):147-54. PubMed PMID: 8795437.

13: Basso N, Kurnjek ML, Ruiz P, Cannata MA. Effect of EXP 3174 on blood pressure of normoreninemic renal hypertensive rats. Hypertension. 1995 Feb;25(2):283-7. PubMed PMID: 7843780.

14: Bartholomeusz B, Widdop RE. Effect of acute and chronic treatment with the angiotensin II subtype 1 receptor antagonist EXP 3174 on baroreflex function in conscious spontaneously hypertensive rats. J Hypertens. 1995 Feb;13(2):219-25. PubMed PMID: 7615952.

15: Widdop RE, Gardiner SM, Kemp PA, Bennett T. Comparison of the regional haemodynamic effects of the AT1-receptor antagonists, losartan and EXP 3174, in water-deprived Brattleboro rats. Br J Pharmacol. 1993 Mar;108(3):684-8. PubMed PMID: 8467356; PubMed Central PMCID: PMC1908057.

16: Osei SY, Minkes RK, Bellan JA, Kadowitz PJ. Analysis of the inhibitory effects of DuP 753 and EXP 3174 on responses to angiotensin II in the feline hindquarters vascular bed. J Pharmacol Exp Ther. 1993 Mar;264(3):1104-12. PubMed PMID: 8450454.

17: Widdop RE, Gardiner SM, Kemp PA, Bennett T. Central administration of PD 123319 or EXP-3174 inhibits effects of angiotensin II. Am J Physiol. 1993 Jan;264(1 Pt 2):H117-25. PubMed PMID: 7679256.

18: Widdop RE, Gardiner SM, Kemp PA, Bennett T. Inhibition of the haemodynamic effects of angiotensin II in conscious rats by AT2-receptor antagonists given after the AT1-receptor antagonist, EXP 3174. Br J Pharmacol. 1992 Nov;107(3):873-80. PubMed PMID: 1472980; PubMed Central PMCID: PMC1907755.