Candesartan
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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

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Candesartan
CAS# 139481-59-7

Theoretical Analysis

MedKoo Cat#: 317364
Name: Candesartan
CAS#: 139481-59-7
Chemical Formula: C24H20N6O3
Exact Mass: 440.15969
Molecular Weight: 440.45
Elemental Analysis: C, 65.45; H, 4.58; N, 19.08; O, 10.90

Price and Availability

Size Price Availability Quantity
100.0mg USD 90.0 Same day
200.0mg USD 150.0 Same day
500.0mg USD 250.0 Same day
1.0g USD 450.0 Same day
2.0g USD 850.0 Same day
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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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

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.

Recalculate based on batch purity %
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: Wolska E, Kluk A, Zarazińska M, Boniecka M, Sznitowska M. Choice of excipients
for gelly-like pulp prepared ex tempore "on a spoon"- "placebo" and with sartans.
Drug Dev Ind Pharm. 2015 Nov 7:1-10. [Epub ahead of print] PubMed PMID: 26548554.

2: Enatsu N, Miyake H, Chiba K, Fujisawa M. Candesartan Mediated Amelioration of
Cisplatin-Induced Testicular Damage Is Associated with Alterations in Expression
Patterns of Nephrin and Podocin. Biomed Res Int. 2015;2015:273784. doi:
10.1155/2015/273784. Epub 2015 Oct 11. PubMed PMID: 26539476; PubMed Central
PMCID: PMC4619786.

3: Quiñones MM, Maldonado L, Velazquez B, Porter JT. Candesartan ameliorates
impaired fear extinction induced by innate immune activation. Brain Behav Immun.
2015 Oct 28. pii: S0889-1591(15)30043-X. doi: 10.1016/j.bbi.2015.10.017. [Epub
ahead of print] PubMed PMID: 26520214.