Product Name

  • Name

    Azelnidipine

  • EINECS 634-143-0
  • CAS No. 123524-52-7
  • Article Data5
  • CAS DataBase
  • Density 1.33 g/cm3
  • Solubility
  • Melting Point 120-126 ºC
  • Formula C33H34N4O6
  • Boiling Point 709.3 ºC at 760 mmHg
  • Molecular Weight 582.656
  • Flash Point 382.8 ºC
  • Transport Information
  • Appearance light yellowish powder
  • Safety 26-39
  • Risk Codes 22-41
  • Molecular Structure Molecular Structure of 123524-52-7 (Azelnidipine)
  • Hazard Symbols HarmfulXn
  • Synonyms Calblock;CS 905;3,5-Pyridinedicarboxylic acid, 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl) 5-(1-methylethyl) ester, (+-)-;3-(1-(Diphenylmethyl)-3-azetidinyl) 5-isopropyl (+-)-2-amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate;Calblock (TN);(1-benzhydrylazetidin-3-yl) propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;Azelidipine;2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxy lic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(methylethyl) ester;
  • PSA 139.71000
  • LogP 6.18470

Synthetic route

3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester
39562-25-9

3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester

1-benzhydrylazetidin-3-yl 3-amino-3-iminopropanoate acetate

1-benzhydrylazetidin-3-yl 3-amino-3-iminopropanoate acetate

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
With sodium amide In toluene for 4h; Reflux;90.01%
With sodium methylate In isopropyl alcohol for 4h; Heating;74%
With sodium methylate In isopropyl alcohol for 4h; Heating / reflux;74%
isopropyl 3-aminocrotonate
14205-46-0

isopropyl 3-aminocrotonate

C26H23N3O5

C26H23N3O5

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
With sodium methylate In ethanol for 6h; Reflux;89%
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / piperidinium acetate / propan-2-ol / 1 h / 45 - 55 °C
2: 74 percent / sodium methoxide / propan-2-ol / 4 h / Heating
View Scheme
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; piperidine / ethanol / 24 h / 20 - 30 °C
2: potassium hydroxide / ethanol; water / 6 h / Reflux
3: dicyclohexyl-carbodiimide / tetrahydrofuran / 10 h / 60 - 70 °C
4: sodium methylate / ethanol / 6 h / Reflux
View Scheme
2-cyano-3-(3'-nitro-1'-phenyl)acrylic acid
5468-46-2

2-cyano-3-(3'-nitro-1'-phenyl)acrylic acid

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / ethanol; water / 6 h / Reflux
2: dicyclohexyl-carbodiimide / tetrahydrofuran / 10 h / 60 - 70 °C
3: sodium methylate / ethanol / 6 h / Reflux
View Scheme
C10H8N2O5

C10H8N2O5

azelnidipine
123524-52-7

azelnidipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / tetrahydrofuran / 10 h / 60 - 70 °C
2: sodium methylate / ethanol / 6 h / Reflux
View Scheme
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

azelnidipine
123524-52-7

azelnidipine

Azelnidipine tosylate

Azelnidipine tosylate

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 1h;100%
azelnidipine
123524-52-7

azelnidipine

Azelnidipine dihydrochloride

Azelnidipine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 25℃; for 0.0833333h; Product distribution / selectivity;100%
With hydrogenchloride In water; ethyl acetate at 25℃; for 1h; Product distribution / selectivity;92%
azelnidipine
123524-52-7

azelnidipine

benzenesulfonic acid
98-11-3

benzenesulfonic acid

Azelnidipine dibenzenesulfonate

Azelnidipine dibenzenesulfonate

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 1h;99%
methanesulfonic acid
75-75-2

methanesulfonic acid

azelnidipine
123524-52-7

azelnidipine

Azelnidipine dimesylate

Azelnidipine dimesylate

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 1h;97%
methanesulfonic acid
75-75-2

methanesulfonic acid

azelnidipine
123524-52-7

azelnidipine

Azelnidipine trimesylate

Azelnidipine trimesylate

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 1h;97%
naphthalene-2-sulfonate
120-18-3

naphthalene-2-sulfonate

azelnidipine
123524-52-7

azelnidipine

Azelnidipine napsylate

Azelnidipine napsylate

Conditions
ConditionsYield
In ethyl acetate at 2 - 25℃; for 97h;97%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

azelnidipine
123524-52-7

azelnidipine

2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester hemifumarate

2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester hemifumarate

Conditions
ConditionsYield
In tetrahydrofuran; ethyl acetate at 25℃; for 0.833333h;93%
azelnidipine
123524-52-7

azelnidipine

2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester monosulfate

2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-(1-diphenylmethylazetidin-3-yl) ester 5-isopropyl ester monosulfate

Conditions
ConditionsYield
With sulfuric acid In acetone at 25℃; for 2.83333h;92%
azelnidipine
123524-52-7

azelnidipine

citric acid
77-92-9

citric acid

Azelnidipine citrate
938439-89-5

Azelnidipine citrate

Conditions
ConditionsYield
In acetone at 25℃; for 1.16667h;79%
azelnidipine
123524-52-7

azelnidipine

Azelnidipine dihydrobromide

Azelnidipine dihydrobromide

Conditions
ConditionsYield
With hydrogen bromide In methanol; water at 25℃; for 1h;78%
azelnidipine
123524-52-7

azelnidipine

A

(-)-Azelnidipine
722455-08-5

(-)-Azelnidipine

B

(+)-Azelnidipine
722455-09-6

(+)-Azelnidipine

Conditions
ConditionsYield
at 25℃; Purification / work up;
maleic acid
110-16-7

maleic acid

azelnidipine
123524-52-7

azelnidipine

azelnidipine-maleic acid complex

azelnidipine-maleic acid complex

Conditions
ConditionsYield
In ethanol; water at 25℃; Thermodynamic data; Temperature;
azelnidipine
123524-52-7

azelnidipine

3-(1-benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
918659-10-6

3-(1-benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 5h; Inert atmosphere;800 mg
azelnidipine
123524-52-7

azelnidipine

aminoazelnidipine

aminoazelnidipine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate
azelnidipine
123524-52-7

azelnidipine

C33H36N4O8

C33H36N4O8

Conditions
ConditionsYield
Stage #1: azelnidipine With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -10℃; for 0.666667h;
Stage #2: With sodium hydrogensulfite In dichloromethane; water for 0.333333h; Temperature;

Azelnidipine Specification

Azelnidipine is a dihydropyridine calcium channel blocker. With the CAS NO.123524-52-7, it has the Synonyms of 3-(1-(Diphenylmethyl)-3-azetidinyl) 5-isopropyl (+-)-2-amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate; Azelnidipine; CCRIS 8650; CS 905; UNII-PV23P19YUG ; 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2-amino-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl) 5-(1-methylethyl) ester, (+-)-.  Azelnidipine, unlike Nicardipine, has a gradual onset and has a long-lasting hypotensive effect, with little increase in heart rate.

Physical properties about Azelnidipine are: (1)ACD/LogP: 5.529; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 4.85; (4)ACD/LogD (pH 7.4): 5.51; (5)ACD/BCF (pH 5.5): 1941.56; (6)ACD/BCF (pH 7.4): 9027.14; (7)ACD/KOC (pH 5.5): 5023.17; (8)ACD/KOC (pH 7.4): 23354.86; (9)#H bond acceptors: 10; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.659; (13)Molar Refractivity: 161.274 cm3; (14)Molar Volume: 437.498 cm3; (15)Polarizability: 63.934 10-24cm3; (16)Surface Tension: 64.1039962768555 dyne/cm; (17)Density: 1.332 g/cm3; (18)Flash Point: 382.779 °C; (19)Enthalpy of Vaporization: 103.735 kJ/mol; (20)Boiling Point: 709.313 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C33H34N4O6/c1-20(2)42-32(38)27-21(3)35-31(34)29(28(27)24-15-10-16-25(17-24)37(40)41)33(39)43-26-18-36(19-26)30(22-11-6-4-7-12-22)23-13-8-5-9-14-23/h4-17,20,26,28,30,35H,18-19,34H2,1-3H3;
(2)InChIKey=ZKFQEACEUNWPMT-UHFFFAOYSA-N;
(3)SmilesC1N(CC1OC(C=1[C@@H](c2cc([N+]([O-])=O)ccc2)C(C(=O)OC(C)C)=C(NC1N)C)=O)C(c1ccccc1)c1ccccc1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 800mg/kg (800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl,
mouse LD50 oral 785mg/kg (785mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl,
rat LD50 oral 1267mg/kg (1267mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA

MUSCULOSKELETAL: OTHER CHANGES		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl,

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