Losartan carboxaldehyde | CAS# 114798-36-6 (carboxaldehyde) | angiotensin II type 1 receptor antagonist

MedKoo Cat#: 414180 | Name: Losartan carboxaldehyde

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Losartan carboxaldehyde is an intermediate aldehyde metabolite of the angiotensin II type 1 receptor antagonist, losartan (Item No. 10006594). It does not block angiotensin receptors, but instead inhibits endothelial cyclooxygenase (COX)-2 expression, thereby exerting anti-inflammatory actions.

Chemical Structure

Losartan carboxaldehyde

CAS#114798-36-6 (carboxaldehyde)

Theoretical Analysis

MedKoo Cat#: 414180

Name: Losartan carboxaldehyde

CAS#: 114798-36-6 (carboxaldehyde)

Chemical Formula: C22H21ClN6O

Exact Mass: 420.1465

Molecular Weight: 420.90

Elemental Analysis: C, 62.78; H, 5.03; Cl, 8.42; N, 19.97; O, 3.80

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

124750-99-8 (Ka+) 114798-26-4 (free) 114798-36-6 (carboxaldehyde)

Synonym

Losartan carboxaldehyde; EXP3179; EXP-3179; EXP 3179

IUPAC/Chemical Name

1H-Imidazole-5-carboxaldehyde, 2-butyl-4-chloro-1-((2'-(2H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-

InChi Key

FQZSMTSTFMNWQF-UHFFFAOYSA-N

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)

SMILES Code

O=CC1=C(Cl)N=C(CCCC)N1CC2=CC=C(C3=CC=CC=C3C4=NNN=N4)C=C2

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

EXP3179 is an important intermediate aldehyde metabolite of Losartan.

In vitro activity:

In TGF-β1-stimulated fibroblasts, EXP3179 inhibited CTGF and LOX expression and activity with lower IC50 values than EXP3174. Reference: Sci Rep. 2017 Feb 3;7:41865. https://pubmed.ncbi.nlm.nih.gov/28157237/

In vivo activity:

In rats treated with NG-nitro-L-arginine methyl ester (L-NAME), administration of EXP3179 fully prevented LOX, CCL and connective tissue growth factor (CTGF) increase, as well as fibrosis, without normalization of blood pressure (BP). Reference: Sci Rep. 2017 Feb 3;7:41865. https://pubmed.ncbi.nlm.nih.gov/28157237/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	71.28
	DMSO	30.0	71.28
	Ethanol	30.0	71.28
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.19

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 420.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Miguel-Carrasco JL, Beaumont J, San José G, Moreno MU, López B, González A, Zalba G, Díez J, Fortuño A, Ravassa S. Mechanisms underlying the cardiac antifibrotic effects of losartan metabolites. Sci Rep. 2017 Feb 3;7:41865. doi: 10.1038/srep41865. PMID: 28157237; PMCID: PMC5291109.

In vitro protocol:

In vivo protocol:

1: Miguel-Carrasco JL, Beaumont J, San José G, Moreno MU, López B, González A, Zalba G, Díez J, Fortuño A, Ravassa S. Mechanisms underlying the cardiac antifibrotic effects of losartan metabolites. Sci Rep. 2017 Feb 3;7:41865. doi: 10.1038/srep41865. PMID: 28157237; PMCID: PMC5291109. 2: Rossi GP. Losartan metabolite EXP3179: an AT1-receptor-independent treatment strategy for patients with the metabolic syndrome? Hypertension. 2009 Oct;54(4):710-2. doi: 10.1161/HYPERTENSIONAHA.109.138883. Epub 2009 Aug 17. PMID: 19687342. 3: Kappert K, Tsuprykov O, Kaufmann J, Fritzsche J, Ott I, Goebel M, Bähr IN, Hässle PL, Gust R, Fleck E, Unger T, Stawowy P, Kintscher U. Chronic treatment with losartan results in sufficient serum levels of the metabolite EXP3179 for PPARgamma activation. Hypertension. 2009 Oct;54(4):738-43. doi: 10.1161/HYPERTENSIONAHA.109.132886. Epub 2009 Aug 17. PMID: 19687349. 4: Wenzel P, Schulz E, Münzel T. Protein kinase C-inhibiting properties of the losartan metabolite EXP3179 make the difference. Hypertension. 2009 Oct;54(4):707-9. doi: 10.1161/HYPERTENSIONAHA.109.136218. Epub 2009 Aug 17. PMID: 19687344. 5: Fortuño A, Bidegain J, Robador PA, Hermida J, López-Sagaseta J, Beloqui O, Díez J, Zalba G. Losartan metabolite EXP3179 blocks NADPH oxidase-mediated superoxide production by inhibiting protein kinase C: potential clinical implications in hypertension. Hypertension. 2009 Oct;54(4):744-50. doi: 10.1161/HYPERTENSIONAHA.109.129353. Epub 2009 Aug 17. Erratum in: Hypertension. 2010 Jul;56(1):e17. PMID: 19687351. 6: Watanabe T, Suzuki J, Yamawaki H, Sharma VK, Sheu SS, Berk BC. Losartan metabolite EXP3179 activates Akt and endothelial nitric oxide synthase via vascular endothelial growth factor receptor-2 in endothelial cells: angiotensin II type 1 receptor-independent effects of EXP3179. Circulation. 2005 Sep 20;112(12):1798-805. doi: 10.1161/CIRCULATIONAHA.104.509760. PMID: 16172287. 7: Schupp M, Lee LD, Frost N, Umbreen S, Schmidt B, Unger T, Kintscher U. Regulation of peroxisome proliferator-activated receptor gamma activity by losartan metabolites. Hypertension. 2006 Mar;47(3):586-9. doi: 10.1161/01.HYP.0000196946.79674.8b. Epub 2005 Dec 19. PMID: 16365190. 8: Véniant M, Clozel JP, Hess P, Fischli W. Effects of renin-angiotensin system blockade in guinea pigs. Hypertension. 1992 Mar;19(3):255-62. doi: 10.1161/01.hyp.19.3.255. PMID: 1532164. 9: Grothusen C, Umbreen S, Konrad I, Stellos K, Schulz C, Schmidt B, Kremmer E, Teebken O, Massberg S, Luchtefeld M, Schieffer B, Gawaz M. EXP3179 inhibits collagen-dependent platelet activation via glycoprotein receptor-VI independent of AT1-receptor antagonism: potential impact on atherothrombosis. Arterioscler Thromb Vasc Biol. 2007 May;27(5):1184-90. doi: 10.1161/ATVBAHA.106.138693. Epub 2007 Mar 8. PMID: 17347483.