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Candesartan
- Iupac Name：2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-
4-carboxylic acid
- CAS No.: 139481-59-7
- Molecular Weight：440.454
- Modify Date.: 2022-11-11 00:38
- Introduction: Candesartan, (+)-1-[[(cyclohexyloxy)carbonyl]-oxy]ethyl 2- ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylate(Atacand), like losartan, possesses the acidic tetrazole system,which most likely plays a role in binding to the angiotensin IIreceptor similarly to the acidic groups of angiotensin II. Also,the imidazole system has been replaced with a benzimidazolepossessing an ester at position. This ester must be hydrolyzedto the free acid. Fortunately, this conversion takesplace fairly easily because of the carbonate in the ester sidechain. This facilitates hydrolysis of the ester so much thatconversion to the free acid takes place during absorption fromthe gastrointestinal tract. Candesartan Preparation Products And Raw materials Raw materials
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1. Names and Identifiers
- 1.1 Name
- Candesartan
- 1.2 Synonyms
1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic 1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)Methyl)-2-ethoxy-1H-benzo[d]iMidazole-7-carboxylic acid 1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- 1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- 2-(ethyloxy)-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid 2-Ethoxy-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic Acid 2-Ethoxy-1-{[2'-(1H-tetrazol-5-yl)-4-biphenylyl]methyl}-1H-benzimidazole-7-carboxylic acid 2-Ethoxy-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid 2-Ethoxy-1-{[2'-(2H-tetrazol-5-yl)-4-biphenylyl]methyl}-1H-benzimidazole-7-carboxylic acid 2-ethoxy-1-{[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid 2-ETHOXY1-2(1H-TETRAZOL-5YL)1,1-BIPHENYL)-4-YL)-4-YL)METHYL)1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]-3h-benzoimidazole-4-carboxylic acid 3-[[2'-(1H-Tetrazol-5-yl)biphenyl-4-yl]Methyl]-2-ethoxy-3H-benziMidazole-4-
carboxylic Acid Amias Atacand Blopress Candesartan Cilexetil EP IMpurity G Candesartan Cilexetil Impurity 7 Candesartan M1 MFCD00864463 Ratacand
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- 1.3 CAS No.
- 139481-59-7
- 1.4 CID
- 2541
- 1.5 EINECS(EC#)
- 604-138-8
- 1.6 Molecular Formula
- C24H20N6O3 (isomer)
- 1.7 Inchi
- 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)
- 1.8 InChIkey
- HTQMVQVXFRQIKW-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)O
- 1.10 Isomers Smiles
- CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)O
2. Properties
- 2.1 Density
- 1.41
- 2.1 Melting point
- 183-185℃
- 2.1 Boiling point
- 754.8 °C at 760 mmHg
- 2.1 Refractive index
- 1.746
- 2.1 Flash Point
- 410.3 °C
- 2.1 Precise Quality
- 440.16000
- 2.1 PSA
- 118.81000
- 2.1 logP
- 4.02860
- 2.1 Appearance
- crystalline solid
- 2.2 Storage
- -20°C Freezer
- 2.3 Chemical Properties
- Crystalline Solid
- 2.4 Color/Form
- Powder
- 2.5 pKa
- 2.06±0.10(Predicted)
- 2.6 Water Solubility
- Insoluble
- 2.7 Stability
- Stable under recommended storage conditions.
- 2.8 StorageTemp
- Inert atmosphere,Store in freezer, under -20°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin eceptor antagonist used for the treatment of hypertension.
- 3.2 General Description
- Candesartan, (+)-1-[[(cyclohexyloxy)carbonyl]-oxy]ethyl 2- ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylate(Atacand), like losartan, possesses the acidic tetrazole system,which most likely plays a role in binding to the angiotensin IIreceptor similarly to the acidic groups of angiotensin II. Also,the imidazole system has been replaced with a benzimidazolepossessing an ester at position. This ester must be hydrolyzedto the free acid. Fortunately, this conversion takesplace fairly easily because of the carbonate in the ester sidechain. This facilitates hydrolysis of the ester so much thatconversion to the free acid takes place during absorption fromthe gastrointestinal tract. Candesartan Preparation Products And Raw materials Raw materials
- 3.3 Usage
- An angiotensin II type-1 receptor antagonist. Used in treatment of congestive heart failure. Antihypertensive
4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- R20/21/22
- 4.1 Safety Statements
- 26-36
- 4.1 Exposure Standards and Regulations
- The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl candesartan cilexetil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Candesartan cilexetil/
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 4.79 (est)
- 4.3 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 Formulations/Preparations
- Oral: Tablets: 4 mg Atacand, (AstraZeneca), 8 mg Atacand, (AstraZeneca), 16 mg Atacand, (AstraZeneca), 32 mg Atacand, (AstraZeneca). /Candesartan cilexetil/
- 4.5 RTECS
- DD6671000
- 4.5 Safety
-
Hazard Codes:?
Xn
Risk Statements: 20/21/22-36/37/38?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
- 4.6 Specification
-
?Candesartan , its cas register number is 139481-59-7. It also can be called?2-Ethoxy-1-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic acid ; 1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)- .It is a?crystalline solid.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Reproductive toxicity, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H361 Suspected of damaging fertility or the unborn child |
| Precautionary statement(s) | |
| Prevention | P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P308+P313 IF exposed or concerned: Get medical advice/ attention. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
139481-59-7Total: 13 Synthesis Route
8. Other Information
- 8.0 Chemical Properties
- Crystalline Solid
- 8.1 Uses
- An angiotensin II type-1 receptor antagonist. Used in treatment of congestive heart failure. Antihypertensive
- 8.2 Uses
- antihypertensive, angiotensin II inhibitor
- 8.3 Definition
- ChEBI: A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin eceptor antagonist used for the treatment of hypertension.
- 8.4 Brand name
- Atacand (AstraZeneca).
- 8.5 Usage
- Candesartan is a selective AT1 (angiotensin II receptor 1) antagonist. Antagonism of angiotensin receptors inhibits vasoconstriction and the production of aldosterone, leading to a decrease in water and sodium concentration in blood plasma. Exhibits antihypertensive effects in animal models. Used in treatment of congestive heart failure, as antihypertensive. Candesartan does not affect cell viability or proliferation but increases the expression of VEGF and interleukin-8 in the cultured medium of KU-19-19 cells. Candesartan (0.1 nM) could reduce the maximal contractile response to angiostensin II by approximately 50%.
- 8.6 General Description
- Candesartan, (+)-1-[[(cyclohexyloxy)carbonyl]-oxy]ethyl 2- ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylate(Atacand), like losartan, possesses the acidic tetrazole system,which most likely plays a role in binding to the angiotensin IIreceptor similarly to the acidic groups of angiotensin II. Also,the imidazole system has been replaced with a benzimidazolepossessing an ester at position. This ester must be hydrolyzedto the free acid. Fortunately, this conversion takesplace fairly easily because of the carbonate in the ester sidechain. This facilitates hydrolysis of the ester so much thatconversion to the free acid takes place during absorption fromthe gastrointestinal tract.
9. Computational chemical data
- Molecular Weight: 440.454g/mol
- Molecular Formula: C24H20N6O3
- Compound Is Canonicalized: True
- XLogP3-AA: 4.1
- Exact Mass: 440.15968852
- Monoisotopic Mass: 440.15968852
- Complexity: 660
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 7
- Topological Polar Surface Area: 119
- Heavy Atom Count: 33
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceB7sAAAAAAAAAAAAAAAAAAAAWLAAAAwYMAAAAAAAFgB/AAAHgAYCAAADAjhnwYz2LcOFgCqAybybACCgC8lEqAd+CE4fNiIbrrAnZGccYhuwAPI2ee8yOCOwAAAQAASACCAAACAACQAQAAAAAAAAA==
10. Question & Answer
-
Candesartan is a medication used to treat high blood pressure and heart failure, belonging to the class of angiotensin II receptor antagonists. But what role does Candesartan play in drug development?..
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After being diagnosed with primary hypertension or other forms of high blood pressure, it is important to actively seek treatment. The causes and symptoms of different types of high blood pressure may..
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Seven types of sartans commonly used in clinical antihypertensive treatment include: irbesartan, losartan, valsartan, candesartan, telmisartan, olmesartan, and allisartan. They all belong to angiotens..
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Background and overview[1][2] Candesartan is the prodrug of candesartan ester, its chemical name is: (±)-1H-benzimidazole-7-carboxylic acid-2-ethoxy-1-{ [2'-(1H-Tetrazol-5-yl)-[1,1'-bip..
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