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Nilvadipine
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Name

Nilvadipine

 EINECS 805-887-5
CAS No. 75530-68-6 Density 1.32 g/cm3
PSA 134.24000 LogP 3.30988
Solubility N/A Melting Point 148-150 °C
Formula C19H19N3O6 Boiling Point 526.7 °C at 760 mmHg
Molecular Weight 385.376 Flash Point 272.3 °C
Transport Information N/A Appearance yellow prisms
Safety Risk Codes 22
Molecular Structure Molecular Structure of 75530-68-6 (Nilvadipine) Hazard Symbols Xn
Synonyms

CL 287389;Escor;FK 235;FR 34235;Nivadil;Nivadip;SKF 102362;dl-Nilvadipine;

Article Data 11

Nilvadipine Synthetic route

1452166-70-9

isopropyl 2-hydroxyiminomethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

75530-68-6

nilvadipine

Conditions
ConditionsYield
With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 10 - 50℃; for 5h;85.1%
186581-53-3, 908094-01-9

diazomethane

sodium 2-cyano-5-isopropoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

A

75530-68-6

nilvadipine

B

145220-80-0

isopropyl 2-carbamoyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1, 4-dihydropyridine-5-carboxylate

Conditions
ConditionsYield
With hydrogenchloride 1.) AcOEt, 2.) AcOEt, ether; Yield given. Multistep reaction. Yields of byproduct given;
75530-60-8

isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

75530-68-6

nilvadipine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate; acetic anhydride 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium acetate / water; methanol / 4 h / 20 °C
2: acetic anhydride; potassium carbonate / dimethyl sulfoxide / 5 h / 10 - 50 °C
View Scheme
39562-25-9

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

4-Amino-3-imino-butyric acid methyl ester; compound with acetic acid

75530-68-6

nilvadipine

Conditions
ConditionsYield
With sodium methylate In isopropyl alcohol Heating;
542-08-5

isopropyl acetoacetate

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / piperidinium acetate / propan-2-ol / 10 h / 45 - 55 °C
2: sodium methoxide / propan-2-ol / Heating
View Scheme
99-61-6

3-nitro-benzaldehyde

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / piperidinium acetate / propan-2-ol / 10 h / 45 - 55 °C
2: sodium methoxide / propan-2-ol / Heating
View Scheme
60705-25-1

4,4-dimethoxy-3-oxo-butyric acid methyl ester

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: piperidine / benzene / 3 h / Heating
2: 51.1 percent / 8.5 h / 95 - 120 °C
3: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature
4: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h
View Scheme
14205-46-0

isopropyl 3-aminocrotonate

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 51.1 percent / 8.5 h / 95 - 120 °C
2: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature
3: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h
View Scheme
99-61-6

3-nitro-benzaldehyde

platinum black

platinum black

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: piperidine / benzene / 3 h / Heating
2: 51.1 percent / 8.5 h / 95 - 120 °C
3: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature
4: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h
View Scheme
67448-15-1

(E,Z)-methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate

75530-68-6

nilvadipine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 51.1 percent / 8.5 h / 95 - 120 °C
2: 95.4 percent / 6 N aq. HCl / acetone / 1 h / Ambient temperature
3: 1.) NH2OH*HCl, NaOAc, 2.) Ac2O / 1.) AcOH, RT, 2.5 h, 2.) AcOH, a) RT, 1.5 h, b) 95 deg C - 100 deg C, 4 h
View Scheme

Nilvadipine Specification

The Nilvadipine, with the CAS registry number 75530-68-6, is also known as 5-Isopropyl 3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate. It belongs to the product categories of Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C19H19N3O6 and molecular weight is 385.37. Its IUPAC name is called 3-O-methyl 5-O-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Physical properties of Nilvadipine: (1)ACD/LogP: 1.72; (2)ACD/LogD (pH 5.5): 1.72; (3)ACD/LogD (pH 7.4): 1.72; (4)ACD/BCF (pH 5.5): 12.03; (5)ACD/BCF (pH 7.4): 12.03; (6)ACD/KOC (pH 5.5): 206.47; (7)ACD/KOC (pH 7.4): 206.47; (8)#H bond acceptors: 9; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.584; (12)Molar Refractivity: 97.1 cm3; (13)Molar Volume: 290 cm3; (14)Surface Tension: 57 dyne/cm; (15)Density: 1.32 g/cm3; (16)Flash Point: 272.3 °C; (17)Enthalpy of Vaporization: 80.11 kJ/mol; (18)Boiling Point: 526.7 °C at 760 mmHg; (19)Vapour Pressure: 3.5E-11 mmHg at 25°C.

Preparation: this chemical can be prepared by 3-nitrobenzaldehyde, piperidine, 4,4 - dimethoxy methyl acetoacetate and acetic acid. This reaction will need 2-amino-2-crotonic acid isopropyl.

Uses of Nilvadipine: it is a calcium channel blocker (CCB) for the treatment of hypertension and chronic major cerebral artery occlusion. It can be used as an antihypertensive and antianginal. it can be used as calcium antagonists of dihydropyridine. Besides, it also can be used for essential hypertension. This chemical's classification codes are Antagonist [calcium channel]; Antihypertensive agents; Calcium channel blockers; Cardiovascular Agents; Drug / Therapeutic Agent; Membrane Transport Modulators; Reproductive Effect.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)C)\C1=C(\NC(/C#N)=C(/C(=O)OC)C1c2cccc([N+]([O-])=O)c2)C
(2)InChI: InChI=1/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3
(3)InChIKey: FAIIFDPAEUKBEP-UHFFFAOYAX

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 3850ug/kg (3.85mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
dog LD50 oral 510mg/kg (510mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
mouse LD50 intravenous 9150ug/kg (9.15mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
mouse LD50 oral 1300mg/kg (1300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
mouse LD50 subcutaneous > 320mg/kg (320mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 intravenous 9650ug/kg (9.65mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 oral 1560mg/kg (1560mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1723, 1987.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.

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