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Details

Stereochemistry ACHIRAL
Molecular Formula C24H20N6O3
Molecular Weight 440.454
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CANDESARTAN

SMILES

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

InChI

InChIKey=HTQMVQVXFRQIKW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C24H20N6O3
Molecular Weight 440.454
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Pharmacological differences among angiotensin II receptor antagonists.
2001
[Angiotensin II type-1 receptor antagonists and diabetes mellitus].
2001
[Angiotensin I receptor blockers for heart failure].
2001
[Angiotensin receptor blockers--significance for the therapy of hypertension].
2001
Angiotensin II AT(1) receptor antagonists and platelet activation.
2001
Involvement of angiotensin II in progression of renal injury in rats with genetic non-insulin-dependent diabetes mellitus (Wistar fatty rats).
2001 Apr
Protective effect of agiotensin II type I receptor antagonist, CV-11974, on ischemia and reperfusion injury of the liver.
2001 Apr 27
Functional role of endogenous endothelin-1 in congestive heart failure treated with angiotensin II receptor antagonist.
2001 Aug
Persistent cardiovascular effects of chronic renin-angiotensin system inhibition following withdrawal in adult spontaneously hypertensive rats.
2001 Aug
Role of nNOS in regulation of renal function in angiotensin II-induced hypertension.
2001 Aug
Antihypertensive efficacy of candesartan in comparison to losartan: the CLAIM study.
2001 Jan-Feb
Cardioprotection with angiotensin converting enzyme inhibitor and angiotensin II type 1 receptor antagonist is not abolished by nitric oxide synthase inhibitor in ischemia-reperfused rabbit hearts.
2001 Jul
The angiotensin II receptor antagonist candesartan cilexetil (TCV-116) ameliorates retinal disorders in rats.
2001 Jul
A forced titration study of antihypertensive efficacy of candesartan cilexetil in comparison to losartan: CLAIM Study II.
2001 Jul
Activation of angiotensin II subtype 2 receptor induces catecholamine release in an extracellular Ca(2+)-dependent manner through a decrease of cyclic guanosine 3',5'-monophosphate production in cultured porcine adrenal medullary chromaffin Cells.
2001 Jul
Angiotensin receptor blockers for chronic heart failure and acute myocardial infarction.
2001 Jul
Angiotensin II activates the GFAT promoter in mesangial cells.
2001 Jul
Effects of candesartan on cough and bronchial hyperresponsiveness in mildly to moderately hypertensive patients with symptomatic asthma.
2001 Jul 17
Case of adrenocorticotropic hormone-independent macronodular adrenal hyperplasia with possible adrenal hypersensitivity to angiotensin II.
2001 Jun
Possible roles of cardiac chymase after myocardial infarction in hamster hearts.
2001 Jun
In vitro and in vivo pharmacology of olmesartan medoxomil, an angiotensin II type AT1 receptor antagonist.
2001 Jun
Efficacy of candesartan cilexetil as add-on therapy in hypertensive patients uncontrolled on background therapy: a clinical experience trial. ACTION Study Investigators.
2001 Jun
Coronary hemodynamic and ventricular responses to angiotensin type 1 receptor inhibition in SHR: interaction with angiotensin type 2 receptors.
2001 Jun
Mildly oxidized low-density lipoprotein acts synergistically with angiotensin II in inducing vascular smooth muscle cell proliferation.
2001 Jun
Effects of TCV-116 on expression of NOS and adrenomedullin in failing heart of Dahl salt-sensitive rats.
2001 Jun
Dose-dependent blockade of the angiotensin II type 1 receptor with losartan in normal volunteers.
2001 Jun
Endogenous angiotensin II in the NTS contributes to sympathetic activation in rats with aortocaval shunt.
2001 Jun
[Angiotensin II receptor antagonists: different or equivalent?].
2001 Jun 16-23
An angiotensin II type 1 receptor blocker, candesartan, increases myocardial apoptosis in rats with acute ischemia-reperfusion.
2001 May
Angiotensin II and its metabolites stimulate PAI-1 protein release from human adipocytes in primary culture.
2001 May
Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats.
2001 May
A candesartan cilexetil/hydrochlorothiazide combination tablet provides effective blood pressure control in hypertensive patients inadequately controlled on monotherapy.
2001 May
[Change from ACE inhibitor, Ca-antagonist or beta-blocker to candesartan cilexetil: better efficacy and tolerance. SWITCH study (German study segment)].
2001 May 11
Reversible renal impairment induced by treatment with the angiotensin II receptor antagonist candesartan in a patient with bilateral renal artery stenosis.
2001 May 17
Angiotensin-II-receptor inhibitors in pregnancy.
2001 May 19
Significance of exaggerated natriuresis after angiotensin AT1 receptor blockade or angiotensin- converting enzyme inhibition in obese Zucker rats.
2001 May-Jun
Effects of angiotensin II type 1 receptor antagonist (candesartan) in preventing fatal ventricular arrhythmias in dogs during acute myocardial ischemia and reperfusion.
2001 Nov
Effects of all-trans retinoic acid on renin-angiotensin system in rats with experimental nephritis.
2001 Nov
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
Ventricular production of natriuretic peptides and ventricular structural remodeling in hypertensive heart failure.
2001 Oct
Role of AT1 and AT2 receptor subtypes in salt-sensitive hypertension induced by sensory nerve degeneration.
2001 Oct
Angiotensin-II type 1 receptor interaction is a major regulator for liver fibrosis development in rats.
2001 Oct
TCV-116 stimulates eNOS and caveolin-1 expression and improves coronary microvascular remodeling in normotensive and angiotensin II-induced hypertensive rats.
2001 Oct
Reliability, validity, and responsiveness of the six-minute walk test in patients with heart failure.
2001 Oct
Autoregulated glomerular filtration rate during candesartan treatment in hypertensive type 2 diabetic patients.
2001 Oct
pK(a) determination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry.
2001 Oct
ERK and p38 MAPK, but not NF-kappaB, are critically involved in reactive oxygen species-mediated induction of IL-6 by angiotensin II in cardiac fibroblasts.
2001 Oct 12
Angiotensin II induces circadian gene expression of clock genes in cultured vascular smooth muscle cells.
2001 Oct 9
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.
2001 Sep
Peripheral administration of an angiotensin II AT(1) receptor antagonist decreases the hypothalamic-pituitary-adrenal response to isolation Stress.
2001 Sep
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 Oct 21 21:29:41 UTC 2019
Edited
by admin
on Mon Oct 21 21:29:41 UTC 2019
Record UNII
S8Q36MD2XX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CANDESARTAN
HSDB   INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
CV-11974
Code English
CANDESARTAN [VANDF]
Common Name English
CANDESARTAN [USAN]
Common Name English
CANDESARTAN CILEXETIL SPECIFIED IMPURITY G [EP]
Common Name English
BLOPRESS
Brand Name English
CANDESARTAN [MI]
Common Name English
CANDESARTAN CILEXETIL RELATED COMPOUND G
USP-RS  
Common Name English
CANDESARTAN [INN]
Common Name English
CANDEMORE
Brand Name English
CANDESARTAN CILEXETIL RELATED COMPOUND G [USP-RS]
Common Name English
CANDESARTAN [HSDB]
Common Name English
CANDESARTAN CILEXETIL IMPURITY G [EP]
Common Name English
1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID, 2-ETHOXY-1-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-
Common Name English
2-ETHOXY-1-(P-(O-1H-TETRAZOL-5-YLPHENYL)BENZYL)-7-BENZIMIDAZOLECARBOXYLIC ACID
Common Name English
CANDESARTAN [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC09DB07
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-VATC QC09CA06
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-ATC C09CA06
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
NDF-RT N0000000070
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-ATC C09DA06
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
NDF-RT N0000175561
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-ATC C09DX06
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-VATC QC09DA06
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
WHO-ATC C09DB07
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
LIVERTOX 141
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
Code System Code Type Description
EVMPD
SUB06070MIG
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
MERCK INDEX
M3012
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY Merck Index
INN
7239
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
ChEMBL
CHEMBL1016
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
WIKIPEDIA
CANDESARTAN
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
ChEMBL
CHEMBL1014
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
MESH
C081643
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
HSDB
139481-59-7
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
PUBCHEM
2541
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
IUPHAR
587
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
DRUG BANK
DB00796
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
NCI_THESAURUS
C65284
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
RXCUI
214354
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY RxNorm
EPA CompTox
139481-59-7
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
LactMed
139481-59-7
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
CAS
139481-59-7
Created by admin on Mon Oct 21 21:29:41 UTC 2019 , Edited by admin on Mon Oct 21 21:29:41 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
PLASMA; URINE
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IMPURITY -> PARENT
Priority toxic pollutant.
IMPURITY -> PARENT
Probable human carcinogen.
PARENT -> IMPURITY
for the calculation of content, multiply the peak area by 0.7.
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY GENOTOXIC->PARENT
NDMA is an organic chemical that is in a family of potent carcinogens.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC