Candesartan cilexetil | CAS#145040-37-5 | AT1 antagonist

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

MedKoo CAT#: 319525

CAS#: 145040-37-5 (cilexetil)

Description: Candesartan cilexetil is a prodrug of the potent, long-acting, and selective angiotensin II type 1 receptor (AT1) antagonist, candesartan. It is rapidly hydrolyzed to candesartan during gastrointestinal absorptio. Candesartan blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in many tissues, such as vascular smooth muscle and the adrenal gland. Its action is, therefore, independent of the pathways for angiotensin II synthesis. Candesartan has much greater affinity ( > 10,000-fold) for the AT1 receptor than for the AT2 receptor.

Chemical Structure

Candesartan cilexetil

CAS# 145040-37-5 (cilexetil)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319525
Name: Candesartan cilexetil
CAS#: 145040-37-5 (cilexetil)
Chemical Formula: C33H34N6O6
Exact Mass: 610.25
Molecular Weight: 610.671
Elemental Analysis: C, 64.91; H, 5.61; N, 13.76; O, 15.72

Price and Availability

Size	Price	Availability
1g	USD 250	2 Weeks
2g	USD 350	2 Weeks
5g	USD 650	2 Weeks
10g	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 139481-59-7 145040-37-5 (cilexetil)

Synonym: TCV-116; TCV 116; TCV116; Candesartan cilexetil

IUPAC/Chemical Name: 1-(((cyclohexyloxy)carbonyl)oxy)ethyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

InChi Key: GHOSNRCGJFBJIB-UHFFFAOYSA-N

InChi Code: InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)

SMILES Code: O=C(OC(C)OC(C1=CC=CC2=C1N(CC3=CC=C(C4=C(C5=NN=NN5)C=CC=C4)C=C3)C(OCC)=N2)=O)OC6CCCCC6

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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Candesartan Cilexetil (TCV-116) is an angiotensin II receptor antagonist with IC50 of 0.26 nM, used in the treatment of hypertension.
In vitro activity:	The objective of this study was to determine whether AT1 receptor inhibition would reduce the innate inflammatory response induced by bacterial lipopolysaccharide (LPS). Monocytes were studied in vitro after incubation with LPS (50 ng/ml) with and without 1 mumol/l candesartan, an AT1 receptor blocker. Human monocytes did not express detectable AT1 receptors, and angiotensin II did not induce inflammatory factor mRNA expression or cytokine release. However, candesartan substantially reduced the LPS-induced expression of the mRNAs for the LPS recognition protein cluster of differentiation 14, the proinflammatory cytokines tumor necrosis factor alpha, interleukin-1 beta and interleukin-6 and the lectin-like oxidized low-density lipoprotein receptor. In addition, candesartan reduced the activation of the nuclear factor kappa B pathway, the tumor necrosis factor alpha and interleukin-6 secretion, and the ROS formation induced by LPS, without affecting the secretion of interleukin-10. It is hypothesized that the anti-inflammatory effects of candesartan in these cells are likely mediated by mechanisms unrelated to AT1 receptor blockade. The results demonstrate that candesartan significantly reduces the innate immune response to LPS in human circulating monocytes. The anti-inflammatory effects of candesartan may be of importance not only in hypertension but also in other inflammatory disorders. Reference: J Hypertens. 2009 Dec;27(12):2365-76. https://pubmed.ncbi.nlm.nih.gov/19730394/
In vivo activity:	To better understand the mechanisms underlying the protective effects of candesartan on the intestinal integrity, fecal SCFAs (shortchain fatty acids) were further quantified. As shown in Fig. 7A, at 12 weeks of age, the amount of acetic acid in the vehicle-treated SHRs was decreased to about 60% of that from the vehicle-treated WKY rats while other SCFA species remained unchanged. No significant changes in the amount of fecal acetic acid were observed in 12-week old candesartan-treated SHRs compared to that from the age-matched vehicle-treated SHRs. By 20 weeks of age, the amount of fecal acetic acid, propionic acid and butyric acid was found to be decreased in the vehicle-treated SHRs compared to that from the age-matched vehicle-treated WKY rats. In distinct contrast, the amount of fecal acetic acid, propionic acid and butyric acid was significantly increased in the candesartan-treated SHRs compared to that from the vehicle-treated SHRs. Meanwhile, although no changes in the amount of fecal isobutyric acid, valeric acid, and isovaleric acid were observed in the vehicle-treated SHRs, candesartan treatment increased the amount of these SCFA species (Fig.7B). These results indicate that prolonged treatment of candesartan results in increased microbial production of SCFAs in SHRs. Reference: Biomed Pharmacother. 2019 Aug;116:109040. https://pubmed.ncbi.nlm.nih.gov/31170664/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.0	81.88

Preparing Stock Solutions

The following data is based on the product molecular weight 610.67 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:
In vitro protocol:	1. Torika N, Asraf K, Apte RN, Fleisher-Berkovich S. Candesartan ameliorates brain inflammation associated with Alzheimer's disease. CNS Neurosci Ther. 2018 Mar;24(3):231-242. doi: 10.1111/cns.12802. Epub 2018 Jan 24. PMID: 29365370; PMCID: PMC6489976. 2. Larrayoz IM, Pang T, Benicky J, Pavel J, Sánchez-Lemus E, Saavedra JM. Candesartan reduces the innate immune response to lipopolysaccharide in human monocytes. J Hypertens. 2009 Dec;27(12):2365-76. doi: 10.1097/HJH.0b013e3283314bc7. PMID: 19730394; PMCID: PMC2928995.
In vivo protocol:	1. Torika N, Asraf K, Apte RN, Fleisher-Berkovich S. Candesartan ameliorates brain inflammation associated with Alzheimer's disease. CNS Neurosci Ther. 2018 Mar;24(3):231-242. doi: 10.1111/cns.12802. Epub 2018 Jan 24. PMID: 29365370; PMCID: PMC6489976. 2. Wu D, Tang X, Ding L, Cui J, Wang P, Du X, Yin J, Wang W, Chen Y, Zhang T. Candesartan attenuates hypertension-associated pathophysiological alterations in the gut. Biomed Pharmacother. 2019 Aug;116:109040. doi: 10.1016/j.biopha.2019.109040. Epub 2019 Jun 3. PMID: 31170664.

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1: Yasuno S, Fujimoto A, Nakagawa Y, Kuwahara K, Ueshima K. Fixed-dose combination therapy of candesartan cilexetil and amlodipine besilate for the treatment of hypertension in Japan. Expert Rev Cardiovasc Ther. 2012 May;10(5):577-83. doi: 10.1586/erc.12.34. Review. PubMed PMID: 22651833.

2: Ardiana F, Lestari ML, Indrayanto G. Candesartan cilexetil. Profiles Drug Subst Excip Relat Methodol. 2012;37:79-112. doi: 10.1016/B978-0-12-397220-0.00003-9. Epub 2012 Mar 19. Review. PubMed PMID: 22469317.

3: Joost A, Schunkert H, Radke PW. Candesartan cilexetil: an update. Expert Opin Pharmacother. 2011 Aug;12(11):1769-80. doi: 10.1517/14656566.2011.587000. Epub 2011 Jun 9. Review. PubMed PMID: 21651457.

4: Hoy SM, Keating GM. Candesartan cilexetil: in children and adolescents aged 1 to <17 years with hypertension. Am J Cardiovasc Drugs. 2010;10(5):335-42. doi: 10.2165/11206300-000000000-00000. Review. PubMed PMID: 20860416.

5: Mengden T, Uen S, Bramlage P. Management of hypertension with fixed dose combinations of candesartan cilexetil and hydrochlorothiazide: patient perspectives and clinical utility. Vasc Health Risk Manag. 2009;5:1043-58. Epub 2009 Dec 29. Review. PubMed PMID: 20057897; PubMed Central PMCID: PMC2801628.

6: Kusumoto K, Mori M, Tanokashira J, Totsuka N. [Pharmacological and clinical properties of ECARD combination tablets LD & HD, fixed-dose combination of candesartan cilexetil and hydrochlorothiazide]. Nihon Yakurigaku Zasshi. 2009 Oct;134(4):217-24. Review. Japanese. PubMed PMID: 19828927.

7: Baguet JP, Barone-Rochette G, Neuder Y. Candesartan cilexetil in the treatment of chronic heart failure. Vasc Health Risk Manag. 2009;5(1):257-64. Epub 2009 Apr 8. Review. PubMed PMID: 19436650; PubMed Central PMCID: PMC2672439.

8: Meredith PA. Candesartan cilexetil--a review of effects on cardiovascular complications in hypertension and chronic heart failure. Curr Med Res Opin. 2007 Jul;23(7):1693-705. Review. PubMed PMID: 17588300.

9: Féghali RE, Nisse-Durgeat S, Asmar R. Effect of candesartan cilexetil on diabetic and non-diabetic hypertensive patients: meta-analysis of five randomized double-blind clinical trials. Vasc Health Risk Manag. 2007;3(1):165-71. Review. PubMed PMID: 17583187; PubMed Central PMCID: PMC1994048.

10: Plosker GL, Keam SJ. Candesartan cilexetil: a pharmacoeconomic review of its use in chronic heart failure and hypertension. Pharmacoeconomics. 2006;24(12):1249-72. Review. PubMed PMID: 17129078.

11: Bönner G, Fuchs W. Long-acting blood pressure reduction by candesartan cilexetil in patients with hypertension. Curr Med Res Opin. 2005 Jun;21(6):935-40. Review. PubMed PMID: 15969893.

12: Fenton C, Scott LJ. Candesartan cilexetil: a review of its use in the management of chronic heart failure. Drugs. 2005;65(4):537-58. Review. PubMed PMID: 15733014.

13: Ross A, Papademetriou V. Candesartan cilexetil in cardiovascular disease. Expert Rev Cardiovasc Ther. 2004 Nov;2(6):829-35. Review. Erratum in: Expert Rev Cardiovasc Ther. 2005 May;3(3):543-4. PubMed PMID: 15500428.

14: Andersen NH, Knudsen ST, Poulsen PL, Poulsen SH, Helleberg K, Eiskjaer H, Hansen KW, Bek T, Mogensen CE. Dual blockade with candesartan cilexetil and lisinopril in hypertensive patients with diabetes mellitus: rationale and design. J Renin Angiotensin Aldosterone Syst. 2003 Jun;4(2):96-9. Review. PubMed PMID: 12806591.

15: Easthope SE, Jarvis B. Candesartan cilexetil: an update of its use in essential hypertension. Drugs. 2002;62(8):1253-87. Review. PubMed PMID: 12010090.

16: Melian EB, Jarvis B. Candesartan cilexetil plus hydrochlorothiazide combination: a review of its use in hypertension. Drugs. 2002;62(5):787-816. Review. PubMed PMID: 11929332.

17: Naka T, Kubo K, Nishikawa K, Inada Y, Furukawa Y. [Angiotensin II receptor antagonists: candesartan cilexetil]. Yakugaku Zasshi. 2000 Dec;120(12):1261-75. Review. Japanese. PubMed PMID: 11193378.

18: Mallion JM, Badguet JP. Putting the efficacy of candesartan cilexetil into perspective: a review of new comparative data. J Hum Hypertens. 2000 Oct;14 Suppl 2:S33-41. Review. PubMed PMID: 11086634.

19: Mancia G, Grassi G. The role of angiotensin II receptor antagonists in hypertension management: focus on candesartan cilexetil. J Hum Hypertens. 2000 Oct;14 Suppl 2:S3-10. Review. PubMed PMID: 11086630.

20: Zannad F. Preserving target-organ function with candesartan cilexetil in patients with hypertension. Blood Press Suppl. 2000;1:36-9. Review. PubMed PMID: 11059635.

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