Candesartan | CV11974 | MedKoo Biosciences Inc

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

MedKoo CAT#: 317364

CAS#: 139481-59-7

Description: Candesartan is an angiotensin II receptor antagonist used mainly for the treatment of hypertension. Candesartan is marketed as the cyclohexyl 1-hydroxyethyl carbonate (cilexetil) ester, known as candesartan cilexetil. Candesartan cilexetil is metabolised completely by esterases in the intestinal wall during absorption to the active candesartan moieity. The use of a prodrug form increases the bioavailability of candesartan. Despite this, absolute bioavailability is relatively poor at 15% (candesartan cilexetil tablets) to 40% (candesartan cilexetil solution). Its IC50 is 15 µg/kg.

Chemical Structure

Candesartan

CAS# 139481-59-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317364
Name: Candesartan
CAS#: 139481-59-7
Chemical Formula: C24H20N6O3
Exact Mass: 440.16
Molecular Weight: 440.450
Elemental Analysis: C, 65.45; H, 4.58; N, 19.08; O, 10.90

Price and Availability

Size	Price	Availability
100mg	USD 90	Ready to ship
200mg	USD 150	Ready to ship
500mg	USD 250	Ready to ship
1g	USD 450	Ready to ship
2g	USD 850	Ready to ship
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: Candesartan, CV11974, CV-1197, CV 11974, Trade names: Blopress, Atacand, Amias, and Ratacand

IUPAC/Chemical Name: 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid

InChi Key: HTQMVQVXFRQIKW-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)

SMILES Code: O=C(C1=C2N(CC3=CC=C(C4=CC=CC=C4C5=NNN=N5)C=C3)C(OCC)=NC2=CC=C1)O

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

Certificate of Analysis:

View CoA: current batch, Lot#A20K04S28

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Candesartan is an angiotensin II receptor antagonist with IC50 of 0.26 nM
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	97.0	220.23

Preparing Stock Solutions

The following data is based on the product molecular weight 440.45 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. 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. 3. 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.
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: Gleiter CH, Jägle C, Gresser U, Mörike K. Candesartan. Cardiovasc Drug Rev. 2004 Winter;22(4):263-84. doi: 10.1111/j.1527-3466.2004.tb00146.x. PMID: 15592574.

2: Ripley TL, Chonlahan JS, Germany RE. Candesartan in heart failure. Clin Interv Aging. 2006;1(4):357-66. doi: 10.2147/ciia.2006.1.4.357. PMID: 18046913; PMCID: PMC2699637.

3: Hajjar I, Okafor M, McDaniel D, Obideen M, Dee E, Shokouhi M, Quyyumi AA, Levey A, Goldstein F. Effects of Candesartan vs Lisinopril on Neurocognitive Function in Older Adults With Executive Mild Cognitive Impairment: A Randomized Clinical Trial. JAMA Netw Open. 2020 Aug 3;3(8):e2012252. doi: 10.1001/jamanetworkopen.2020.12252. PMID: 32761160; PMCID: PMC7411539.

4: Ostergren J. Candesartan for the treatment of hypertension and heart failure. Expert Opin Pharmacother. 2004 Jul;5(7):1589-97. doi: 10.1517/14656566.5.7.1589. PMID: 15212609.

5: McKelvie RS. Candesartan for the management of heart failure: more than an alternative. Expert Opin Pharmacother. 2006 Oct;7(14):1945-56. doi: 10.1517/14656566.7.14.1945. PMID: 17020420.

6: Gleiter CH, Mörike KE. Clinical pharmacokinetics of candesartan. Clin Pharmacokinet. 2002;41(1):7-17. doi: 10.2165/00003088-200241010-00002. PMID: 11825094.

7: Doggrell SA; SCOPE (Study of Cognition and Prognosis in the Elderly) and ACCESS ( evaluation of acute candesartan cilexetil in stroke survivors) Trials. Candesartan for the prevention and treatment of stroke - results of the SCOPE and ACCESS trials. Expert Opin Pharmacother. 2004 Mar;5(3):687-90. doi: 10.1517/14656566.5.3.687. PMID: 15013936.

8: Mimran A, Alfaro V. Candesartan: nephroprotective effects and treatment of diabetic nephropathy. Drugs Today (Barc). 2003 Jun;39(6):439-50. doi: 10.1358/dot.2003.39.6.799449. PMID: 12944996.

9: Macconi D, Remuzzi G. Candesartan and renal protection: more than blocking angiotensin type 1 receptor? Kidney Int. 2008 Nov;74(9):1112-4. doi: 10.1038/ki.2008.420. PMID: 18854846.

10: Morsing P. Candesartan: a new-generation angiotensin II AT1 receptor blocker: pharmacology, antihypertensive efficacy, renal function, and renoprotection. J Am Soc Nephrol. 1999 Jan;10 Suppl 11:S248-54. PMID: 9892173.

11: Barrios V, Escobar C, Calderon A. Candesartan: from left ventricular hypertrophy to heart failure, a global approach. Expert Rev Cardiovasc Ther. 2007 Sep;5(5):825-34. doi: 10.1586/14779072.5.5.825. Erratum in: Expert Rev Cardiovasc Ther. 2007 Nov;5(6):1171. PMID: 17867913.

12: Neuper L, Kummer D, Forstner D, Guettler J, Ghaffari-Tabrizi-Wizsy N, Fischer C, Juch H, Nonn O, Gauster M. Candesartan Does Not Activate PPARγ and Its Target Genes in Early Gestation Trophoblasts. Int J Mol Sci. 2022 Oct 14;23(20):12326. doi: 10.3390/ijms232012326. PMID: 36293183; PMCID: PMC9603971.

13: Hermida Pérez B, Izquierdo Romero M, García López R. Candesartan-induced cholestatic hepatitis: a case report. Rev Esp Enferm Dig. 2020 Dec;112(12):959-960. doi: 10.17235/reed.2020.6988/2020. PMID: 33226250.

14: Qie S, Ran Y, Lu X, Su W, Li W, Xi J, Gong W, Liu Z. Candesartan modulates microglia activation and polarization via NF-κB signaling pathway. Int J Immunopathol Pharmacol. 2020 Jan-Dec;34:2058738420974900. doi: 10.1177/2058738420974900. PMID: 33237822; PMCID: PMC7691946.

15: Messina R, Lastarria Perez CP, Filippi M, Goadsby PJ. Candesartan in migraine prevention: results from a retrospective real-world study. J Neurol. 2020 Nov;267(11):3243-3247. doi: 10.1007/s00415-020-09989-9. Epub 2020 Jun 15. PMID: 32542525.

16: Armstrong PW, Lorell BH, Nissen S, Borer J. Candesartan. Circulation. 2002 Aug 6;106(6):e9011-2. PMID: 12163443.

17: Zhenfeng Zheng, Huilan Shi, Junya Jia, Dong Li, Shan Lin. A systematic review and meta-analysis of candesartan and losartan in the management of essential hypertension. J Renin Angiotensin Aldosterone Syst. 2011 Sep;12(3):365-74. doi: 10.1177/1470320310391503. Epub 2011 Mar 18. PMID: 21421652.

18: Khedr NF, Werida RH, Abo-Saif MA. Candesartan protects against d-galactose induced - Neurotoxicity and memory deficit via modulation of autophagy and oxidative stress. Toxicol Appl Pharmacol. 2022 Jan 15;435:115827. doi: 10.1016/j.taap.2021.115827. Epub 2021 Dec 11. PMID: 34906534.

19: Zhang L, Yang F, Yan Q. Candesartan ameliorates vascular smooth muscle cell proliferation via regulating miR-301b/STAT3 axis. Hum Cell. 2020 Jul;33(3):528-536. doi: 10.1007/s13577-020-00333-x. Epub 2020 Mar 13. PMID: 32170715.

20: Ding Y, Lang Y, Zhang H, Li Y, Liu X, Li M. Candesartan Reduces Neuronal Apoptosis Caused by Ischemic Stroke via Regulating the FFAR1/ITGA4 Pathway. Mediators Inflamm. 2022 Sep 7;2022:2356507. doi: 10.1155/2022/2356507. PMID: 36117589; PMCID: PMC9473906.

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