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76095-16-4

Basic Information
CAS No.: 76095-16-4
Name: Enalapril maleate
Article Data: 11
Molecular Structure:
Molecular Structure of 76095-16-4 (Enalapril maleate)
Formula: C24H32N2O9
Molecular Weight: 492.526
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;
EINECS: 278-375-7
Melting Point: 143-144.5°C
Boiling Point: 765.3 °C at 760 mmHg
Flash Point: 416.7 °C
Solubility: methanol: ≥50 mg/mL, clear, colorless to yellow
Appearance: White to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36/37-26
PSA: 170.54000
LogP: 1.64520
Synthetic route
75847-73-3

enalapril

110-16-7

maleic acid

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%
110-16-7

maleic acid

147-85-3

L-proline

406213-94-3

C18H26N2O4

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%
82009-36-7

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

110-16-7

maleic acid

A

76095-16-4

Amprace

Conditions
ConditionsYield
In acetonitrileA 34%
B n/a
82717-96-2

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

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
103377-40-8

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

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
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

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
2812-46-6

proline tert-butyl ester

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
80828-38-2

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

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
108428-39-3

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

76095-16-4

Amprace

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / ethyl acetate
2: 53 percent / ethyl acetate; ethanol
View Scheme
80828-26-8

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

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
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    Product name: Enalapril Maleate CAS No.: 76095-16-4 Molecule Formula:C24H32N2O9 Molecule Weight:492.52 Purity: 99.0% Package: 25kg/drum Description:White or off-white crystalline powder Manufacture Standards:Enterprise Standard

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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.