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=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)
Molecular Formula | C24H20N6O3 |
Molecular Weight | 440.454 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
Target ID: CHEMBL227 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 Date1998 |
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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 Date1998 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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 |
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 Sources: |
unhealthy, 41 years |
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 |
|
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: |
unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F 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 Health Status: unhealthy 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 Sources: |
unhealthy, 41 years |
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: |
unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F Sources: |
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: |
unhealthy, 67 years Health Status: unhealthy Age Group: 67 years Sex: M+F 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 Health Status: unhealthy 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 Health Status: unhealthy 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 |
|
[Angiotensin II type-1 receptor antagonists and diabetes mellitus]. | 2001 |
|
[Angiotensin receptor blockers--significance for the therapy of hypertension]. | 2001 |
|
Antihypertensive treatment in elderly patients aged 75 years or over: a 24-week study of the tolerability of candesartan cilexetil in relation to hydrochlorothiazide. | 2001 |
|
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 |
|
Renal vascular responses to captopril and to candesartan in patients with type 1 diabetes mellitus. | 2001 Apr |
|
AT1 receptor antagonist combats oxidative stress and restores nitric oxide signaling in the SHR. | 2001 Apr |
|
Direct effects of candesartan and eprosartan on human cloned potassium channels involved in cardiac repolarization. | 2001 Apr |
|
[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 |
|
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 |
|
Alterations of the renin-angiotensin system at the RVLM of transgenic rats with low brain angiotensinogen. | 2001 Feb |
|
Angiotensin II type 1 receptor blockers. | 2001 Feb 13 |
|
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 |
|
Glial angiotensinogen regulates brain angiotensin II receptors in transgenic rats TGR(ASrAOGEN). | 2001 Jan |
|
Effects of candesartan on cough and bronchial hyperresponsiveness in mildly to moderately hypertensive patients with symptomatic asthma. | 2001 Jul 17 |
|
[Angiotensin II receptor antagonists: different or equivalent?]. | 2001 Jun 16-23 |
|
The angiotensin II AT1 receptor antagonist irbesartan prevents thromboxane A2-induced vasoconstriction in the rat hind-limb vascular bed in vivo. | 2001 Mar |
|
Lithium intoxication after administration of AT1 blockers. | 2001 Mar |
|
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 |
|
Tight binding of the angiotensin AT(1) receptor antagonist. | 2001 May 15 |
|
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 |
|
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 |
|
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 |
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).
Substance Class |
Chemical
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S8Q36MD2XX
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WHO-VATC |
QC09DB07
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WHO-VATC |
QC09CA06
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WHO-ATC |
C09CA06
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NDF-RT |
N0000000070
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C09DA06
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NCI_THESAURUS |
C66930
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NDF-RT |
N0000175561
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WHO-ATC |
C09DX06
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QC09DA06
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C09DB07
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LIVERTOX |
NBK548409
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m3012
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7239
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CHEMBL1016
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CANDESARTAN
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Candesartan
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA; URINE
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
Priority toxic pollutant.
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IMPURITY -> PARENT |
Probable human carcinogen.
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IMPURITY GENOTOXIC->PARENT |
NDMA is an organic chemical that is in a family of potent carcinogens.
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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