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 |
---|---|---|---|
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 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 |
---|---|---|
[Angiotensin receptor blockers--significance for the therapy of hypertension]. | 2001 |
|
The comparative pharmacology of angiotensin II receptor antagonists. | 2001 |
|
The effect duration of candesartan cilexetil once daily, in comparison with enalapril once daily, in patients with mild to moderate 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 |
|
Effects of quinapril on expression of eNOS, ACE, and AT1 receptor in deoxycorticosterone acetate-salt hypertensive rats. | 2001 Apr |
|
Comparison of candesartan versus enalapril in essential hypertension. Italian Candesartan Study Group. | 2001 Feb |
|
Angiotensin II type 1 receptor blockers. | 2001 Feb 13 |
|
ACE inhibitor and AT1 antagonist blockade of deformation-induced gene expression in the rabbit jugular vein through B2 receptor activation. | 2001 Jan |
|
Antihypertensive efficacy of candesartan in comparison to losartan: the CLAIM study. | 2001 Jan-Feb |
|
In vitro and in vivo pharmacology of olmesartan medoxomil, an angiotensin II type AT1 receptor antagonist. | 2001 Jun |
|
The influence of chronic antihypertensive treatment on the central pressor response in SHR. | 2001 Mar |
|
Effects of AT1 receptor antagonist on proteoglycan gene expression in hypertensive rats. | 2001 Mar |
|
Lithium intoxication after administration of AT1 blockers. | 2001 Mar |
|
Perceived benefit after participating in positive or negative/neutral heart failure trials: the patients' perspective. | 2001 Mar |
|
Combination treatment effective option for hypertensive, diabetic patients with microalbuminuria. | 2001 Mar 20 |
|
Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats. | 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 |
|
Tight binding of the angiotensin AT(1) receptor antagonist. | 2001 May 15 |
|
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 |
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)