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Name	Felodipine	EINECS	620-472-7
CAS No.	72509-76-3	Density	1.277 g/cm³
PSA	64.63000	LogP	4.29310
Solubility	insoluble in water	Melting Point	142-145 °C
Formula	C₁₈H₁₉Cl₂NO₄	Boiling Point	471.5 °C at 760 mmHg
Molecular Weight	384.259	Flash Point	239 °C
Transport Information	N/A	Appearance	White or light yellow crystalline powder
Safety	36	Risk Codes	22
Molecular Structure		Hazard Symbols	Xn
Synonyms	Hydac;Munobal;Plendil;Prevex;Splendil;dl-Felodipine;3,5-Pyridinedicarboxylicacid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester(9CI);Agon;Delmuno;Feloday;Flodil;H 154/82;	Article Data	21

Felodipine Synthetic route

: 68064-64-2, 94739-24-9, 68064-63-1
2-<(2,3-dichlorophenyl)methylene>-3-oxobutanoic acid ethyl ester

: 21731-17-9
methyl 3-aminocrotonate

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In ethanol for 0.075h; Irradiation; Teflon vessel, microwave oven;	96%

: 626-34-6
ethyl 3-aminobut-2-enoate

: 105-45-3
acetoacetic acid methyl ester

: 6334-18-5
2,3-dichlorobenzylaldehyde

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
Stage #1: ethyl 3-aminobut-2-enoate; acetoacetic acid methyl ester; 2,3-dichlorobenzylaldehyde With piperidine; pyridine In neat (no solvent) at 75 - 80℃; for 9h; Stage #2: With ethanol for 1h; Reagent/catalyst; Solvent; Reflux;	94.3%

: ethyl aminocrotonate

: 68064-69-7
(Z)-methyl 2-(2,3-dichlorobenzylidene)-3-oxobutanoate

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In isopropyl alcohol for 12h; Heating / reflux;	86%

: 1352187-23-5
C33H34Cl2N2O7S

: 124-41-4
sodium methylate

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In methanol chemoselective reaction;	84%

: 68064-64-2, 94739-24-9, 68064-63-1
2-<(2,3-dichlorophenyl)methylene>-3-oxobutanoic acid ethyl ester

: 81777-30-2
1,1,1-Triphenyl-3-methyl-4-(methoxycarbonyl)-2-aza-1λ5-phosphabuta-1,3-diene

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 24h;	82%

: 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoethyl ester

: 74-88-4
methyl iodide

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 24h;	70%

: ethyl aminocrotonate

: 105-45-3
acetoacetic acid methyl ester

: 6334-18-5
2,3-dichlorobenzylaldehyde

A: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

B: 91189-59-2
4-(-2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl ester

C: 79925-38-5
4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: acetoacetic acid methyl ester; 2,3-dichlorobenzylaldehyde; piperidine; 2-Picolinic acid In isopropyl alcohol at 40 - 45℃; for 6h; Stage #2: ethyl aminocrotonate In isopropyl alcohol for 4h; Heating / reflux;	A 66% B n/a C n/a

...Expand

: dimethyl dihydropyridine

: diethyl dihydropyridine

: 626-34-6
ethyl 3-aminobut-2-enoate

: 6334-18-5
2,3-dichlorobenzylaldehyde

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
In hexane; isopropyl alcohol	62%

: 94739-24-9
ethyl 2-(2,3-dichlorobenzylidene)-3-oxobutanoate

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / 2-methyl-propan-2-ol / 96 h / 25 °C 2: 72.7 percent / DBU / methanol / 48 h / 25 °C 3: 70 percent / K2CO3 / dimethylformamide / 24 h / 25 °C View Scheme

: 175688-78-5
4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-ethyl ester

: 72509-76-3
ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72.7 percent / DBU / methanol / 48 h / 25 °C 2: 70 percent / K2CO3 / dimethylformamide / 24 h / 25 °C View Scheme

Felodipine Chemical Properties

Molecular Structure:
Molecular Formula: C₁₈H₁₉Cl₂NO₄
Molecular Weight: 384.2538
IUPAC Name: 3-O-Ethyl 5-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Synonyms of Felodipine (CAS NO.72509-76-3): (+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate ; AGON SR ; Agon ; BRN 4331472 ; Feloday ; Felodipina ; Felodipina [INN-Spanish] ; Felodipinum ; Felodipinum [INN-Latin] ; Felodur ER ; Felogard ; Flodil ; H 154/82 ; Hydac ; Modip ; Munobal ; Munobal Retard ; Plendil Depottab ; Plendil ER ; Plendil Retard ; Preslow ; Prevex ; Renedil ; Splendil ; UNII-OL961R6O2C ; dl-Felodipine ; 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-4-(2,3-dichlorophenyl)-2,6-dimethyl-, ethyl methyl ester ; 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, ethyl methyl ester, (+-)-
CAS NO: 72509-76-3
Classification Code: Anti-arrhythmia agents ; Antihypertensive agents ; Calcium channel blockers ; Cardiovascular Agents ; Drug / Therapeutic Agent ; Human Data ; Membrane Transport Modulators ; Reproductive Effect ; Vasodilator ; Vasodilator agents
Melting point: 142-145°C
Index of Refraction: 1.549
Molar Refractivity: 95.78 cm³
Molar Volume: 300.8 cm³
Surface Tension: 42.1 dyne/cm
Density: 1.277 g/cm³
Flash Point: 239 °C
Enthalpy of Vaporization: 73.43 kJ/mol
Boiling Point: 471.5 °C at 760 mmHg
Vapour Pressure: 4.62E-09 mmHg at 25°C

Felodipine Uses

Felodipine (CAS NO.72509-76-3) is a CALCIUM channel blocker, a drug used to control hypertension, or with other antihypertensives, chronic angina pectoris.

Felodipine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	oral	200mg/kg (200mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: CHANGES IN SPLEEN	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20, Pg. 2963, 1992.
mouse	LD50	intraperitoneal	76mg/kg (76mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
mouse	LD50	intravenous	3100ug/kg (3.1mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
mouse	LD50	oral	250mg/kg (250mg/kg)		Cardiovascular Drug Reviews. Vol. 11, Pg. 126, 1993.
mouse	LD50	subcutaneous	205mg/kg (205mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat	LD50	intraperitoneal	23mg/kg (23mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat	LD50	intravenous	5400ug/kg (5.4mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat	LD50	oral	1050mg/kg (1050mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.
rat	LD50	subcutaneous	> 600mg/kg (600mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 239, 1995.

Felodipine Safety Profile

Hazard Codes of of Felodipine (CAS NO.72509-76-3): Harmful Xn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 36
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: US7968700

Felodipine Specification

Interactions:
Recent findings have suggested that felodipine in combination with grapefruit juice will make toxic effects. Oral administration of felodipine is first metabolized in the gastrointestinal tract and liver by the enzyme CYP3A4. Grapefruit juice contains bergamottin that is found to have an inhibiting effect over this enzyme, so as a result the bioavailability of the drug increases, raising the risk for abnormal side effects.

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