CANDESARTAN CILEXETIL

Details

Stereochemistry	RACEMIC
Molecular Formula	C33H34N6O6
Molecular Weight	610.6597
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5)C(=CC=C2)C(=O)OC(C)OC(=O)OC6CCCCC6

InChI

InChIKey=GHOSNRCGJFBJIB-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C33H34N6O6
Molecular Weight	610.6597
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020838s039lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.japsonline.com/admin/php/uploads/290_pdf.pdf

Candesartan is classified as an angiotensin II receptor type 1 antagonist. Candesartan is an orally active lipophilic drug and possesses rapid oral absorption. It causes a reduction in blood pressure and is used in the treatment of hypertension. It is also used in the treatment of congestive heart failure and given as prophylaxis to reduce the severity and duration of migraine. Candesartan cilexetil, a prodrug of Candesartan, is available in the market under the trade names Atacand, Amias. Candesartan cilexetil is rapidly converted to candesartan, its active metabolite, during absorption from the gastrointestinal tract. Candesartan confers blood pressure lowering effects by antagonizing the hypertensive effects of angiotensin II via the RAAS (renin–angiotensin–aldosterone system). RAAS is a homeostatic mechanism for regulating hemodynamics, water, and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering the cardiovascular structure. Angiotensin II binds to two receptors: type-1 angiotensin II receptor (AT1) and type-2 angiotensin II receptor (AT2). Candesartan selectively blocks the binding of angiotensin II to AT1 in many tissues including vascular smooth muscle and the adrenal glands. This inhibits the AT1-mediated vasoconstrictive and aldosterone-secreting effects of angiotensin II and results in an overall decrease in blood pressure. Candesartan is greater than 10,000 times more selective for AT1 than AT2.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Type-1 angiotensin II receptor 41 Target ID: CHEMBL227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020838s039lbl.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020838s039lbl.pdf	Primary		Approved 8583	ATACAND Approved Use Candesartan Cilexetil Tablets are an angiotensin II receptor blocker (ARB) indicated for: •Treatment of hypertension in adults and children 1 to < 17 years of age (1.1). •Treatment of heart failure (NYHA class II-IV); candesartan cilexetil tablets reduces cardiovascular death and heart failure hospitalization (1.2). 1.1 Hypertension Candesartan cilexetil tablets are indicated for the treatment of hypertension in adults and children 1 to < 17 years of age. It may be used alone or in combination with other antihypertensive agents. 1.2 Heart Failure Candesartan cilexetil tablets is indicated for the treatment of heart failure (NYHA class II-IV) in adults with left ventricular systolic dysfunction (ejection fraction ≤ 40%) to reduce cardiovascular death and to reduce heart failure hospitalizations [see CLINICAL STUDIES (14.2) Launch Date 1998
Heart failure 106 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020838s039lbl.pdf	Primary		Approved 8583	ATACAND Approved Use Candesartan Cilexetil Tablets are an angiotensin II receptor blocker (ARB) indicated for: •Treatment of hypertension in adults and children 1 to < 17 years of age (1.1). •Treatment of heart failure (NYHA class II-IV); candesartan cilexetil tablets reduces cardiovascular death and heart failure hospitalization (1.2). 1.1 Hypertension Candesartan cilexetil tablets are indicated for the treatment of hypertension in adults and children 1 to < 17 years of age. It may be used alone or in combination with other antihypertensive agents. 1.2 Heart Failure Candesartan cilexetil tablets is indicated for the treatment of heart failure (NYHA class II-IV) in adults with left ventricular systolic dysfunction (ejection fraction ≤ 40%) to reduce cardiovascular death and to reduce heart failure hospitalizations [see CLINICAL STUDIES (14.2) Launch Date 1998

C_max

Value	Dose	Analyte	Population
55 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
92 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
485 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1359 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
509 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1152 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
15.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10192757	8 mg 1 times / day multiple, oral dose: 8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANDESARTAN CILEXETIL serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020838s041lbl.pdf	unknown, unknown		CANDESARTAN CILEXETIL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11141435	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11141435	Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/11141435
32 mg 1 times / day steady, oral Highest studied dose Dose: 32 mg, 1 times / day Route: oral Route: steady Dose: 32 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12502672	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sources: https://pubmed.ncbi.nlm.nih.gov/12502672	Sources: https://pubmed.ncbi.nlm.nih.gov/12502672
23 mg 1 times / day steady, oral Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	Disc. AE: Hypotension, Hyperkalemia... AEs leading to discontinuation/dose reduction: Hypotension (4.1%) Hyperkalemia (2.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	Other AEs: Disorder fetal... Other AEs: Disorder fetal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (0.6%) Dizziness (0.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf

AEs

AE	Significance	Dose	Population
Hepatitis	acute, 1 patient Disc. AE	16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11141435	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/11141435
Hyperkalemia	2.4% Disc. AE	23 mg 1 times / day steady, oral Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
Hypotension	4.1% Disc. AE	23 mg 1 times / day steady, oral Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
Disorder fetal		16 mg 1 times / day steady, oral Recommended Dose: 16 mg, 1 times / day Route: oral Route: steady Dose: 16 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
Dizziness	0.3% Disc. AE	2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf
Headache	0.6% Disc. AE	2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020838s036lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3347	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3347
ChemicalBook	CB0209324	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0209324
eMolecules	32278092	https://www.emolecules.com/cgi-bin/more?vid=32278092
eMolecules	901501	https://www.emolecules.com/cgi-bin/more?vid=901501
MolPort	MolPort-003-845-570	https://www.molport.com/shop/molecule-link/MolPort-003-845-570
MolPort	MolPort-005-943-739	https://www.molport.com/shop/molecule-link/MolPort-005-943-739
Selleck Chemicals	Candesartan(Atacand)	http://www.selleckchem.com/products/Candesartan(Atacand).html
ZINC	ZINC000003782818	http://zinc15.docking.org/substances/ZINC000003782818

PubMed

Title	Date	PubMed
Angiotensin II and serotonin potentiate endothelin-1-induced vascular smooth muscle cell proliferation.	2001 Apr	11330876
Temporary treatment of prepubescent rats with angiotensin inhibitors suppresses the development of hypertensive nephrosclerosis.	2001 Apr	11274226
Angiotensin blockade inhibits increased JNKs, AP-1 and NF- kappa B DNA-binding activities in myocardial infarcted rats.	2001 Apr	11273732
['Licorice hypertension' also caused by licorice tea].	2001 Apr 14	11332259
Functional role of endogenous endothelin-1 in congestive heart failure treated with angiotensin II receptor antagonist.	2001 Aug	11564281
Cyclic stretch and hypertension induce retinal expression of vascular endothelial growth factor and vascular endothelial growth factor receptor-2: potential mechanisms for exacerbation of diabetic retinopathy by hypertension.	2001 Feb	11272159
Comparison of candesartan versus enalapril in essential hypertension. Italian Candesartan Study Group.	2001 Feb	11243303
New competition in the realm of renin-angiotensin axis inhibition; the angiotensin II receptor antagonists in congestive heart failure.	2001 Jan	11197588
Antihypertensive efficacy of candesartan in comparison to losartan: the CLAIM study.	2001 Jan-Feb	11416677
Angiotensin II activates the GFAT promoter in mesangial cells.	2001 Jul	11399656
Case of adrenocorticotropic hormone-independent macronodular adrenal hyperplasia with possible adrenal hypersensitivity to angiotensin II.	2001 Jun	11572327
Possible roles of cardiac chymase after myocardial infarction in hamster hearts.	2001 Jun	11459123
In vitro and in vivo pharmacology of olmesartan medoxomil, an angiotensin II type AT1 receptor antagonist.	2001 Jun	11451212
Coronary hemodynamic and ventricular responses to angiotensin type 1 receptor inhibition in SHR: interaction with angiotensin type 2 receptors.	2001 Jun	11408384
Effects of TCV-116 on expression of NOS and adrenomedullin in failing heart of Dahl salt-sensitive rats.	2001 Jun	11395021
Dose-dependent blockade of the angiotensin II type 1 receptor with losartan in normal volunteers.	2001 Jun	11392465
[Angiotensin II receptor antagonists: different or equivalent?].	2001 Jun 16-23	11471284
Role of angiotensin II type 1 receptor in the leucocytes and endothelial cells of brain microvessels in the pathogenesis of hypertensive cerebral injury.	2001 Mar	11327634
Effects of AT1 receptor antagonist on proteoglycan gene expression in hypertensive rats.	2001 Mar	11325076
Lithium intoxication after administration of AT1 blockers.	2001 Mar	11305712
Perceived benefit after participating in positive or negative/neutral heart failure trials: the patients' perspective.	2001 Mar	11246060
Comparative effects of candesartan cilexetil and amlodipine in patients with mild systemic hypertension. Comparison of Candesartan and Amlodipine for Safety, Tolerability and Efficacy (CASTLE) Study Investigators.	2001 Mar 15	11249891
Angiotensin II and its metabolites stimulate PAI-1 protein release from human adipocytes in primary culture.	2001 May	11358950
Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats.	2001 May	11358938
A candesartan cilexetil/hydrochlorothiazide combination tablet provides effective blood pressure control in hypertensive patients inadequately controlled on monotherapy.	2001 May	11349825
Do vascular compartments differ in the development of chronic rejection? AT(1) blocker candesartan versus Ace blocker enalapril in an experimental heart transplant model.	2001 Oct	11595564
Autoregulated glomerular filtration rate during candesartan treatment in hypertensive type 2 diabetic patients.	2001 Oct	11576357
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.	2001 Sep	11522611

Patents

Sample Use Guides

In Vivo Use Guide

Adult Hypertension: 2 DOSAGE AND ADMINISTRATION 2.1 Adult Hypertension The usual recommended starting dose of ATACAND (candesartan cilexetil) is 16 mg once daily when it is used as monotherapy in patients who are not volume depleted. ATACAND can be administered once or twice daily with total daily doses ranging from 8 mg to 32 mg. Pediatric Hypertension 1 to < 17 Years of Age: Children 1 to < 6 years of age: The dose range is 0.05 to 0.4 mg/kg per day. The recommended starting dose is 0.20 mg/kg (oral suspension). Children 6 to < 17 years of age: For those less than 50 kg, the dose range is 2 to 16 mg per day. The recommended starting dose is 4 to 8 mg. For those greater than 50 kg, the dose range is 4 to 32 mg per day. The recommended starting dose is 8 to 16 mg. Adult Heart Failure: The recommended initial dose for treating heart failure is 4 mg once daily. The target dose is 32 mg once daily, which is achieved by doubling the dose at approximately 2-week intervals, as tolerated by the patient.

Route of Administration: Oral

In Vitro Use Guide

Primary cultures of human retinal endothelial cells (EC) were candesartan treatment (1μg/ml).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:29 GMT 2025`
Record UNII	R85M2X0D68
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANDESARTAN 1-(((CYCLOHEXYLOXY)CARBONYL)OXY)ETHYL ESTER

Preferred Name

English

CANDESARTAN CILEXETIL

Official Name

English

ATACAND

Brand Name

English

CANDESARTAN CILEXETIL [VANDF]

Common Name

English

CANDESARTAN CILEXETIL [USP-RS]

Common Name

English

CANDESARTAN CILEXETIL [MART.]

Common Name

English

TCV-116

Code

English

1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID, 2-ETHOXY-1-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, 1-(((CYCLOHEXYLOXY)CARBONYL)OXY)ETHYL ESTER, (±)-

Common Name

English

CANDESARTAN CILEXETIL [USAN]

Common Name

English

NSC-758697

Code

English

CANDESARTAN CILEXETIL [ORANGE BOOK]

Common Name

English

CANDESARTAN 1-(((CYCLOHEXYLOXY)CARBONYL)OXY)ETHYL ESTER [MI]

Common Name

English

CANDESARTAN CILEXETIL [EP MONOGRAPH]

Common Name

English

CANDESARTAN CILEXETIL [USP MONOGRAPH]

Common Name

English

(±)-1-HYDROXYETHYL 2-ETHOXY-1-(P-(O-1H-TETRAZOL-5-YLPHENYL)BENZYL)-7-BENZIMIDAZOLECARBOXYLATE, CYCLOHEXYL CARBONATE (ESTER)

Common Name

English

Candesartan cilexetil [WHO-DD]

Common Name

English

CANDESARTAN CILEXETIL [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66930