Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H20N6O3 |
Molecular Weight | 440.454 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=C(C=CC=C4)C5=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)
DescriptionCurator's Comment: description was created based on several sources, including
http://www.japsonline.com/admin/php/uploads/290_pdf.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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8205603
Curator's Comment: TCV-116 # Takeda, Osaka, Japan
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL227 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ATACAND Approved UseCandesartan 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 Date8.9691842E11 |
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Primary | ATACAND Approved UseCandesartan 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 Date8.9691842E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
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 Co-administed with:: amlodipine(10 mg/day) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis (acute, 1 patient) Sources: |
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: |
unhealthy, 59 years n = 6 Health Status: unhealthy Condition: Type 2 Diabetes Age Group: 59 years Population Size: 6 Sources: |
|
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
Disc. AE: Hypotension, Hyperkalemia... AEs leading to discontinuation/dose reduction: Hypotension (4.1%) Sources: Hyperkalemia (2.4%) |
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: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Disorder fetal... Other AEs: Disorder fetal Sources: |
2 mg 1 times / day steady, oral Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (0.6%) Sources: Dizziness (0.3%) |
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 Co-administed with:: amlodipine(10 mg/day) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
Hyperkalemia | 2.4% Disc. AE |
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
Hypotension | 4.1% Disc. AE |
23 mg 1 times / day steady, oral (mean) Recommended Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: |
unhealthy, 67 years n = 207 Health Status: unhealthy Condition: heart failure Age Group: 67 years Sex: M+F Population Size: 207 Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
|
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: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
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: |
unhealthy n = 2350 Health Status: unhealthy Population Size: 2350 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Distinction between surmountable and insurmountable selective AT1 receptor antagonists by use of CHO-K1 cells expressing human angiotensin II AT1 receptors. | 1999 Feb |
|
Binding of the antagonist [3H]candesartan to angiotensin II AT1 receptor-transfected [correction of tranfected] Chinese hamster ovary cells. | 1999 Feb 19 |
|
Effect of beta(2)-adrenoceptor activation and angiotensin II on tumour necrosis factor and interleukin 6 gene transcription in the rat renal resident macrophage cells. | 1999 Oct |
|
The mechanism of action of angiotensin II is dependent on direct activation of vascular smooth muscle carbonic anhydrase I. | 2000 |
|
Angiotensin II AT(1) receptor antagonists and platelet activation. | 2001 |
|
Efficacy and tolerability of angiotensin II type 1 receptor antagonists in dialysis patients using AN69 dialysis membranes. | 2001 |
|
Expanded role for ARBs in cardiovascular and renal disease? Recent observations have far-reaching implications. | 2001 Apr |
|
Inhibition of platelet activation in stroke-prone spontaneously hypertensive rats: comparison of losartan, candesartan, and valsartan. | 2001 Apr |
|
Temporary treatment of prepubescent rats with angiotensin inhibitors suppresses the development of hypertensive nephrosclerosis. | 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 |
|
[Clinical study of the month. The CALM study assessing the combination of an angiotensin-converting enzyme inhibitor and an angiotensin II receptor antagonist in the treatment of diabetic nephropathy]. | 2001 Feb |
|
Comparison of candesartan versus enalapril in essential hypertension. Italian Candesartan Study Group. | 2001 Feb |
|
Mechanisms underlying renoprotection during renin-angiotensin system blockade. | 2001 Feb |
|
Alterations of the renin-angiotensin system at the RVLM of transgenic rats with low brain angiotensinogen. | 2001 Feb |
|
Myocardial ischemia activates the JAK-STAT pathway through angiotensin II signaling in in vivo myocardium of rats. | 2001 Feb |
|
Effects of TCV-116 on endothelin-1 and PDGF A-chain expression in angiotensin II-induced hypertensive rats. | 2001 Jan |
|
New competition in the realm of renin-angiotensin axis inhibition; the angiotensin II receptor antagonists in congestive heart failure. | 2001 Jan |
|
Renin angiotensin system-dependent hypertrophy as a contributor to heart failure in hypertensive rats: different characteristics from renin angiotensin system-independent hypertrophy. | 2001 Jan |
|
ACE inhibitor and AT1 antagonist blockade of deformation-induced gene expression in the rabbit jugular vein through B2 receptor activation. | 2001 Jan |
|
Glial angiotensinogen regulates brain angiotensin II receptors in transgenic rats TGR(ASrAOGEN). | 2001 Jan |
|
A forced titration study of antihypertensive efficacy of candesartan cilexetil in comparison to losartan: CLAIM Study II. | 2001 Jul |
|
Angiotensin II activates the GFAT promoter in mesangial cells. | 2001 Jul |
|
Case of adrenocorticotropic hormone-independent macronodular adrenal hyperplasia with possible adrenal hypersensitivity to angiotensin II. | 2001 Jun |
|
Endogenous angiotensin II in the NTS contributes to sympathetic activation in rats with aortocaval shunt. | 2001 Jun |
|
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 |
|
Effects of angiotensin IV and angiotensin-(1-7) on basal and angiotensin II-stimulated cytosolic Ca2+ in mesangial cells. | 2001 Mar 2 |
|
Combination treatment effective option for hypertensive, diabetic patients with microalbuminuria. | 2001 Mar 20 |
|
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 |
|
Ventricular production of natriuretic peptides and ventricular structural remodeling in hypertensive heart failure. | 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 |
|
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25420481
Primary cultures of human retinal endothelial cells (EC) were candesartan treatment (1μg/ml).
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ACTIVE MOIETY
METABOLITE (PARENT)