An active metabolite of losartan
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Parent Compound(s)
10006594Losartan (potassium salt)
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Losartan Carboxaldehyde

Item No. 18855

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxaldehyde
CAS Number
114798-36-6
Synonyms
  • DuP-167
  • E3179
  • EXP3179
Molecular Formula
C22H21ClN6O
Formula Weight
420.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
249, 273 nm
SMILES
[H]N1N=NN=C1C2=CC=CC=C2C3=CC=C(CN4C(C([H])=O)=C(Cl)N=C4CCCC)C=C3
InChi Code
InChI=1S/C22H21ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,14H,2-3,8,13H2,1H3,(H,25,26,27,28)
InChi Key
FQZSMTSTFMNWQF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

    $168

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    10 mg

    $274

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    Product Description

    Losartan carboxaldehyde is an active metabolite of the angiotensin II type 1b (AT1b) receptor antagonist losartan (Item No. 10006594).1 It is formed from losartan by the cytochrome P450 (CYP) isoforms CYP2C9 and CYP3A4. Losartan carboxaldehyde (10 pM) inhibits platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in isolated human platelet-rich plasma.2 It is an agonist of peroxisome proliferator-activated receptor γ (PPARγ; EC50 = 17.1 µM in COS-7 cells expressing human PPARγ using a reporter assay).3 Losartan carboxaldehyde (10 µM) increases lipid accumulation, a marker of differentiation, in 3T3-L1 adipocytes.3 It decreases superoxide production by NADPH oxidase (NOX) in isolated human peripheral blood mononuclear cells (PBMCs) in a concentration-dependent manner.4 Losartan carboxaldehyde (10 µM) inhibits LPS-induced increases in COX2 mRNA expression and LPS- or angiotensin II-induced increases in supernatant prostaglandin F2α (PGF2α; Item Nos. 16010 | 16020) levels in human umbilical vein endothelial cells (HUVECs).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. R.A., S., Chakravarty, P.K., Chen, R., et al. Biotransformation of losartan to its active carboxylic acid metabolite in human liver microsomes. Role of cytochrome P4502C and 3A subfamily members. Drug Metab. Dispos. 23(2), 207-215 (1995).

    2. Krämer, C., Sunkomat, J., Witte, J., et al. Angiotensin II receptor-independent antiinflammatory and antiaggregatory properties of losartan: Role of the active metabolite EXP3179. Circ. Res. 90(7), 770-776 (2002).

    3. Schupp, M., Lee, L.D., Frost, N., et al. Regulation of peroxisome proliferator-activated receptor γ activity by losartan metabolites. Hypertension 47(3), 586-589 (2006).

    4. Fortuño, A., Bidegain, J., Robador, P.A., et al. Losartan metabolite EXP3179 blocks NADPH oxidase-mediated superoxide production by inhibiting protein kinase C: Potential clinical implications in hypertension. Hypertension 54(4), 744-750 (2009).