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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 of CANDESARTAN CILEXETIL

SMILES

CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=C(C=CC=C4)C5=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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ATACAND
Primary
ATACAND

Cmax

ValueDoseCo-administeredAnalytePopulation
92 ng/mL
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
61 ng/mL
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
79 ng/mL
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
55 ng/mL
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1152 ng × h/mL
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
509 ng × h/mL
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
1359 ng × h/mL
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
485 ng × h/mL
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
7.1 h
8 mg 1 times / day multiple, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
12 h
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens
6.7 h
8 mg single, oral
CANDESARTAN CILEXETIL serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
unknown, unknown
CANDESARTAN CILEXETIL plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
R85M2X0D68
Record Status Validated (UNII)
Record Version