Product Name

  • Name

    Enalapril maleate

  • EINECS 278-375-7
  • CAS No. 76095-16-4
  • Article Data11
  • CAS DataBase
  • Density
  • Solubility methanol: ≥50 mg/mL, clear, colorless to yellow
  • Melting Point 143-144.5°C
  • Formula C24H32N2O9
  • Boiling Point 765.3 °C at 760 mmHg
  • Molecular Weight 492.526
  • Flash Point 416.7 °C
  • Transport Information
  • Appearance White to off-white crystalline powder
  • Safety 22-24/25-36/37-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 76095-16-4 (Enalapril maleate)
  • Hazard Symbols IrritantXi
  • Synonyms Enalapril maleate (JAN/USP);L-Proline,N-[(1S)-1-(ethoxycarbonyl)-3- phenylpropyl]-L-alanyl-,(2Z)-2-butenedioate (1:1);Prestwick_197;Vasotec (TN);Vasotec;but-2-enedioic acid; (2S)-1-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid;Renivace (TN);MK 421;Renivace;
  • PSA 170.54000
  • LogP 1.64520

Synthetic route

enalapril
75847-73-3

enalapril

maleic acid
110-16-7

maleic acid

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
at 5 - 30℃; for 7h;92%
at 30 - 50℃; for 6h;90%
In water at 5 - 60℃; for 4h;90%
maleic acid
110-16-7

maleic acid

L-proline
147-85-3

L-proline

C18H26N2O4
406213-94-3

C18H26N2O4

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Stage #1: L-proline; C18H26N2O4 With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 20℃; for 8h;
Stage #2: maleic acid In ethyl acetate at 20℃; for 3h; Further stages.;		92%
...Expand
N-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-L-proline
82009-36-7

N-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-L-proline

maleic acid
110-16-7

maleic acid

A

Amprace
76095-16-4

Amprace

B

enalapril maleic acid
76095-16-4, 76420-75-2, 82009-37-8, 119815-10-0

enalapril maleic acid

Conditions
ConditionsYield
In acetonitrileA 34%
B n/a
...Expand
[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine
82717-96-2

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: HCl / CH2Cl2; dioxane / -5 - 0 °C
1.2: ClCOCOCl / dimethylformamide; CH2Cl2; dioxane / -5 - 0 °C
2.1: dimethylformamide; CH2Cl2; dioxane / 1 h / 20 °C
3.1: DBU / acetonitrile; CH2Cl2 / 8 h / 20 °C
3.2: 92 percent / ethyl acetate / 3 h / 20 °C
View Scheme
N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine acid chloride
103377-40-8

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine acid chloride

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylformamide; CH2Cl2; dioxane / 1 h / 20 °C
2.1: DBU / acetonitrile; CH2Cl2 / 8 h / 20 °C
2.2: 92 percent / ethyl acetate / 3 h / 20 °C
View Scheme
2-oxo-4-phenylbutanoic acid ethyl ester
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 29 percent / H2, AcONa, AcOH, molecular sieves 3A / Raney Ni / ethanol
2: 93 percent / HCl / H2O / 4 h
3: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h
4: HCl / ethyl acetate
5: 53 percent / ethyl acetate; ethanol
View Scheme
proline tert-butyl ester
2812-46-6

proline tert-butyl ester

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h
2: HCl / ethyl acetate
3: 53 percent / ethyl acetate; ethanol
View Scheme
N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester
80828-38-2

N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 93 percent / HCl / H2O / 4 h
2: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h
3: HCl / ethyl acetate
4: 53 percent / ethyl acetate; ethanol
View Scheme
N--L-alanyl>-L-proline tert butyl ester
108428-39-3

N--L-alanyl>-L-proline tert butyl ester

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / ethyl acetate
2: 53 percent / ethyl acetate; ethanol
View Scheme
N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride
80828-26-8

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h
2: HCl / ethyl acetate
3: 53 percent / ethyl acetate; ethanol
View Scheme
Multi-step reaction with 3 steps
1.1: (chloromethylene)dimethyliminium chloride / dichloromethane / 0.67 h / -10 - -5 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: hydrogen; palladium 10% on activated carbon / methanol / 15 - 20 °C
3.1: acetonitrile; tert-butyl methyl ether / 20 °C
View Scheme
1H-imidazole
288-32-4

1H-imidazole

aqueous sodium chloride

aqueous sodium chloride

silylated L-proline

silylated L-proline

water
7732-18-5

water

N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
877932-98-4

N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

maleic acid
110-16-7

maleic acid

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
With thionyl chloride; sodium chloride In dichloromethane; ethyl acetate
...Expand
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (chloromethylene)dimethyliminium chloride / dichloromethane / 0.67 h / -10 - -5 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: hydrogen; palladium 10% on activated carbon / methanol / 15 - 20 °C
3.1: acetonitrile; tert-butyl methyl ether / 20 °C
View Scheme
N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester
120924-94-9

N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester

Amprace
76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen; palladium 10% on activated carbon / methanol / 15 - 20 °C
2: acetonitrile; tert-butyl methyl ether / 20 °C
View Scheme
Amprace
76095-16-4

Amprace

N-[(S)-ethoxycarbonyl-3-cyclohexylpropyl]-L-alanyl-L-proline

N-[(S)-ethoxycarbonyl-3-cyclohexylpropyl]-L-alanyl-L-proline

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen; acetic acid In ethanol at 25℃; under 1292.9 - 1551.49 Torr; for 96h;30%
Amprace
76095-16-4

Amprace

enalaprilate
76420-72-9

enalaprilate

Conditions
ConditionsYield
With sodium hydroxide In water Ambient temperature;
With porcine liver esterase In phosphate buffer at 37℃; pH=8.6;
Amprace
76095-16-4

Amprace

A

C20H26N2O4
256510-64-2

C20H26N2O4

B

enalaprilate
76420-72-9

enalaprilate

Conditions
ConditionsYield
With water at 40℃; for 13149h;

Enalapril maleate Specification

The Enalapril maleate with the cas number 76095-16-4, is also called (Z)-but-2-enedioic acid; (2S)-1-[(2S)-2-[[(2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid. It's system Name are (1) (S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline maleate (1:1); (2) L-Proline, 1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-, (S)-, (Z)-2-butenedioate (1:1); (3) L-Proline, N-((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl-, (2Z)-2-butenedioate (1:1). It belongs to the following product categories: (1)All Inhibitors; (2)Inhibitors; (3)Intermediates & Fine Chemicals; (4)Pharmaceuticals; (5)Enalapril and so on.

Physical properties about Enalapril maleate are: (1)ACD/LogP: 2.418; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 11; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 12; (6)Flash Point: 416.7 °C; (7)Enthalpy of Vaporization: 116.92 kJ/mol; (8)Boiling Point: 765.3 °C at 760 mmHg; (9)Vapour Pressure: 1.25E-24 mmHg at 25°C

Uses of Enalapril maleate: This drug is used to treat high blood pressure (hypertension) in adults and children. It belongs to a group of medications called ACE inhibitors which can relax blood vessels, causing them to widen, lowering high blood pressure helps prevent strokes, heart attacks and kidney problems. This medication is also used with other drugs (e.g., "water pills"/diuretics, digoxin) to treat congestive heart failure. Besides, this medication may also be used to help protect the kidneys from damage due to diabetes.

When you are using this chemical, please be cautious about it as the following: It is quite irritating to eyes, respiratory system and skin. When you are using this chemical, you should better wear suitable protective clothing and gloves to avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure :
(1).SMILES: O=C(O)[C@@H]2CCCN2C(=O)[C@H](C)NC(CCc1ccccc1)C(=O)OCC.OC(=O)/C=C\C(O)=O
(2).InChI:InChI=1/C20H28N2O5.C4H4O4/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25;5-3(6)1-2-4(7)8/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,16?,17-;/m0./s1

Toxic information of Enalapril maleate can be showed as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 71ug/kg (.071mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION British Medical Journal. Vol. 291, Pg. 1309, 1985.
man TDLo oral 143ug/kg (.143mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 294, Pg. 91, 1987.
man TDLo oral 357ug/kg/3D-I (.357mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA American Journal of Emergency Medicine. Vol. 8, Pg. 124, 1990.
mouse LD50 intravenous 859mg/kg (859mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
mouse LD50 oral 3507mg/kg (3507mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
mouse LD50 subcutaneous 1160mg/kg (1160mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
rat LD50 intravenous 849mg/kg (849mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
rat LD50 oral 2973mg/kg (2973mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
rat LD50 subcutaneous 1418mg/kg (1418mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 413, 1985.
women TDLo oral 400ug/kg/2D-I (.4mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 294, Pg. 91, 1987.
women TDLo oral 2800ug/kg/4W- (2.8mg/kg) KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION		 British Medical Journal. Vol. 291, Pg. 450, 1985.
women TDLo oral 4mg/kg/10D-I (4mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED		 Annals of Pharmacotherpy. Vol. 27, Pg. 1405, 1993.
women TDLo oral 5600ug/kg/4W- (5.6mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Lancet. Vol. 2, Pg. 1395, 1986.
women TDLo oral 39500ug/kg/56 (39.5mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Journal of Family Practice. Vol. 34, Pg. 201, 1992.

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