EXP3174


Catalog No. size PriceQuantity
M6459-2 2mg solid $105
M6459-10 10mg solid $436

Description

Cas:124750-92-1

Product Information

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

 

Synonym: 

 

EXP-3174

EXP 3174

EXP3174

E-3174

E 3174

E3174

Losartan Carboxylic Acid

 

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

 

In Vitro

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.

 

In Vivo

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.

 

 

References

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

Products are for research use only. Not for human use.

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