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| CAS No.: | 76095-16-4 |
|---|---|
| Name: | Enalapril maleate |
| Article Data: | 11 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 22-24/25-36/37-26 |
| PSA: | 170.54000 |
| LogP: | 1.64520 |
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| Conditions | Yield |
|---|---|
| at 5 - 30℃; for 7h; | 92% |
| at 30 - 50℃; for 6h; | 90% |
| In water at 5 - 60℃; for 4h; | 90% |
| Conditions | Yield |
|---|---|
| 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
B
- 76095-16-4, 76420-75-2, 82009-37-8, 119815-10-0
enalapril maleic acid
| Conditions | Yield |
|---|---|
| In acetonitrile | A 34% B n/a |
- 82717-96-2
[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine
- 76095-16-4
Amprace
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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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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. |