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Candesartan cilexetil
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Name

Candesartan cilexetil

 EINECS 627-030-2
CAS No. 145040-37-5 Density 1.37 g/cm3
PSA 143.34000 LogP 6.31910
Solubility N/A Melting Point 168-170?C
Formula C33H34N6O6 Boiling Point 843.3 ºC at 760 mmHg
Molecular Weight 610.67 Flash Point 463.8 ºC
Transport Information N/A Appearance White crystalline powder
Safety 26-36 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 145040-37-5 (Candesartan cilexetil) Hazard Symbols HarmfulXn
Synonyms

1H-Benzimidazolium, 7-carboxy-1-(2-((cyclohexylcarbonyl)oxy)ethyl)-2-ethoxy-1-(2-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)-, hydroxide, inner salt, (+-)-;TCV-116;Atacand;Atacand (TN);1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzoimidazole-4-carboxylate;TCV 116;Candesartancilexetil;

Article Data 41

Candesartan cilexetil Synthetic route

170791-09-0

cilexetil trityl candesartan

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With hydrogenchloride In methanol; dichloromethane at -14 - -12℃; Temperature; Flow reactor; Large scale;98%
With iron(III) chloride In methanol; dichloromethane at 23℃; for 48h; Time; Reagent/catalyst;96%
With methanol; zinc(II) chloride In butanone at 20 - 40℃; for 2.5h; Product distribution / selectivity;95.23%
78-09-1

orthocarbonic acid tetraethyl ester

1236156-65-2

2-(((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-aminobenzoic acid-1-(((cyclohexyloxy)carbonyl)oxy)ethyl ester

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With acetic acid In ethyl acetate at 30℃; Temperature;93.9%
With acetic acid In toluene at 60℃; for 2h;81%
78-09-1

orthocarbonic acid tetraethyl ester

C30H32N6O5*C2H2O4

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
Stage #1: C30H32N6O5*C2H2O4 With potassium carbonate In ethyl acetate at 10 - 15℃; pH=6 - 7;
Stage #2: orthocarbonic acid tetraethyl ester In acetic acid at 0 - 25℃; for 15h;		92.3%
1307853-85-5

1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 1-({4-[2-(1-benzyl-1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-2-ethoxy-1H-1,3-benzodiazole-7-carboxylate

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 25℃; for 14h; Temperature; Time;92.1%
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 25℃; for 14h;80%
With ammonium formate; palladium over charcoal In water; isopropyl alcohol at 55 - 60℃; for 12 - 15h;
With rosenmund catalyst; ammonium formate In water; isopropyl alcohol
1N-HCl

1N-HCl

170791-09-0

cilexetil trityl candesartan

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With sodium bicarbonate In methanol; dichloromethane; water; ethyl acetate75%
139481-72-4

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With water In methanol; toluene for 2 - 4h; Product distribution / selectivity; Heating / reflux;67%
1307853-79-7

C41H42N6O7

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With ammonium formate; 5%-palladium/activated carbon In water; isopropyl alcohol at 40 - 50℃; for 17h;55%
139481-72-4

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

1N-HCl

1N-HCl

95789-69-8, 102672-57-1

cyclohexyl (1-iodoethyl)carbonate

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With potassium carbonate In methanol; ethanol; water; N,N-dimethyl-formamide
methanolic hydrogen chloride

methanolic hydrogen chloride

170791-09-0

cilexetil trityl candesartan

111-87-5

octanol

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethanol; hexane; dichloromethane; water; acetone
170791-09-0

cilexetil trityl candesartan

A

869631-11-8

(1RS)-1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-oxo-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-2,3-dihydro-1H-benzimidazole-4-carboxylate

B

145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With methanol for 24h; Product distribution / selectivity; Heating / reflux;
With methanol; formic acid In dichloromethane at 25℃; for 5 - 23h; Product distribution / selectivity;
Stage #1: cilexetil trityl candesartan With methanol; water; zinc(II) chloride for 2.5h; Heating / reflux;
Stage #2: With water; sodium hydrogencarbonate In methanol at 20℃; pH=6.11; Product distribution / selectivity;

Candesartan cilexetil Specification

1. Introduction of Candesartan cilexetil
Candesartan cilexetil is one kind of white or off white powder. The IUPAC Name of it is 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate. It belongs to Antihypertensive;API;APIs;Hypertension;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Candesartan;Heterocycles. The Classification Code of it is Angiotensin II Type 1 Receptor Blockers; Angiotensin Receptor Antagonists; Antagonist [angiotensin II receptor]; Antihypertensive; Antihypertensive agents; Cardiovascular Agents; Drug / Therapeutic Agent.

2. Properties of Candesartan cilexetil
Physical properties about Candesartan cilexetil are:
(1)Index of Refraction: 1.666; (2)Molar Refractivity: 165.46 cm3; (3)Molar Volume: 444.6 cm3; (4)Surface Tension: 54 dyne/cm; (5)Density: 1.37 g/cm3; (6)Flash Point: 463.8 °C; (7)Enthalpy of Vaporization: 122.54 kJ/mol; (8)Boiling Point: 843.3 °C at 760 mmHg; (9)Vapour Pressure of Candesartan cilexetil: 1.11E-28 mmHg at 25 °C.

3. Structure Descriptors of Candesartan cilexetil
(1)SMILES: c1cc(c2c(c1)nc(OCC)n2Cc1ccc(cc1)c1ccccc1c1[nH]nnn1)C(O[C@@H](OC(OC1CCCCC1)=O)C)=O
(2)InChI: InChI=1/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)
(3)InChIKey: InChIKey=GHOSNRCGJFBJIB-UHFFFAOYSA-N

4. Toxicity of Candesartan cilexetil

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 2gm/kg (2000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 406, 2000.
mouse LD50 intraperitoneal 807mg/kg (807mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24(Suppl,
mouse LD50 oral > 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24(Suppl,
rat LD50 intraperitoneal 940mg/kg (940mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24(Suppl,
rat LD50 oral > 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 24(Suppl,

5. Safety of Candesartan cilexetil
Hazard Codes: HarmfulXn
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 of Candesartan cilexetil (CAS NO.145040-37-5): 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.

6. Uses of Candesartan cilexetil
Candesartan cilexetil (CAS NO.145040-37-5) is used in treatment of congestive heart failure. As an antihypertensive, it will be used in treatment of congestive heart failure.

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