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Name |
Lisinopril |
EINECS | 278-488-1 |
CAS No. | 76547-98-3 | Density | 1.251 g/cm3 |
PSA | N/A | LogP | N/A |
Solubility | ≥10 mg/mL in water | Melting Point |
162-165 °C |
Formula | C21H31N3O5 | Boiling Point | 666.4 °C at 760 mmHg |
Molecular Weight | 405.494 | Flash Point | 356.9 °C |
Transport Information | N/A | Appearance | white solid |
Safety | 22-24/25 | Risk Codes | N/A |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
L-Proline,1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-, (S)-;Alapril;Carace;Cipral;Cipril;Coric;Diroton;Listril;Lizonoton;Longes;MK521;MK 522;N-(1(S)-Carboxy-3-phenylpropyl)-L-lysyl-L-proline;N2-[(S)-1-Carboxy-3-phenylpropyl]-L-lysyl-L-proline;Nanopril;Novatec;Presiten;Prinil;Prinivil;Tensopril;Tensyn;Vivatec;Zestril; |
Article Data | 12 |
Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline
Lisinopril
Conditions | Yield |
---|---|
With water; sodium hydroxide at 40 - 45℃; pH=12 - 13; | 92% |
N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline
Lisinopril
Conditions | Yield |
---|---|
With sodium hydroxide for 24h; Ambient temperature; | 75.8% |
(S)-1-[N2-(1-carboxy-3-phenylpropyl]-L-lysyl]-L-proline
A
Lisinopril
B
lisinopril
Conditions | Yield |
---|---|
With hydrogenchloride In water Resolution of racemate; | A 75% B n/a |
2-oxo-4-phenylbutyric acid
H-Lys(Boc)-Pro-OH
A
Lisinopril
B
lisinopril
Conditions | Yield |
---|---|
With sodium hydroxide; Dowex 50 (H+, 50-100 mesh); sodium cyanoborohydride 1.) water, room temperature, pH 7.0; Yield given. Multistep reaction. Yields of byproduct given; |
Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline
A
Lisinopril
B
lisinopril
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hydrogencarbonate at 40℃; for 4h; | A 75 % Chromat. B n/a |
With sodium hydroxide; sodium hydrogencarbonate at 40℃; for 4h; Title compound not separated from byproducts; |
N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester
Lisinopril
Conditions | Yield |
---|---|
With sodium hydroxide; trifluoroacetic acid Multistep reaction; | |
Multi-step reaction with 2 steps 1: 89 percent / TFA / 24 h / Ambient temperature 2: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme |
Lisinopril
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal |
L-proline benzyl ester hydrochloride
Lisinopril
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / Et3N, dicyclohexylcarbodiimide / CH2Cl2 / 0 deg C, 1 h -> room temperature, 15 h 2: 78 percent / H2 / Pd/C / ethanol; acetic acid / 15 h / 2068.6 Torr / Ambient temperature 3: 1.) aq. NaOH, aq. NaBH3CN, 2.) Dowex 50 (H+, 50-100 mesh) / 1.) water, room temperature, pH 7.0 View Scheme |
N-(N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester
Lisinopril
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / H2 / Pd/C / ethanol; acetic acid / 15 h / 2068.6 Torr / Ambient temperature 2: 1.) aq. NaOH, aq. NaBH3CN, 2.) Dowex 50 (H+, 50-100 mesh) / 1.) water, room temperature, pH 7.0 View Scheme |
Lisinopril
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / Et3N, dicyclohexylcarbodiimide / CH2Cl2 / 0 deg C, 1 h -> room temperature, 15 h 2: 78 percent / H2 / Pd/C / ethanol; acetic acid / 15 h / 2068.6 Torr / Ambient temperature 3: 1.) aq. NaOH, aq. NaBH3CN, 2.) Dowex 50 (H+, 50-100 mesh) / 1.) water, room temperature, pH 7.0 View Scheme |
Historically,after captopril and enalapril, Lisinopril (CAS NO.76547-98-3) was the third ACE inhibitor, and was introduced into therapy in the early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half-life and tissue penetration and is not metabolized by the liver.
The Lisinopril, with the CAS registry number 76547-98-3, is also known as N2-((S)-1-Carboxy-3-phenylpropyl)-L-lysyl-L-proline. Its EINECS number is 278-488-1. This chemical's molecular formula is C21H31N3O5 and molecular weight is 405.49. What's more, its systematic name is N2-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Human Data. Its storage temperature is 2-8 °C. Moreover, it should be protected from oxides. You should not breathe dust. When using it, you must avoid contact with eyes. It is one of the angiotensin-converting enzyme inhibitors (ace inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure, acute myocardial infarction, and diabetic nephropathy. It can be used as antihypertensive drugs such as angiotensin converting enzyme inhibitors.
Physical properties of Lisinopril are: (1)ACD/LogP: 1.19; (2)# of Rule of 5 Violations: 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 8; (8)#H bond donors: 5; (9)#Freely Rotating Bonds: 13; (10)Polar Surface Area: 79.39 Å2; (11)Index of Refraction: 1.577; (12)Molar Refractivity: 107.48 cm3; (13)Molar Volume: 323.9 cm3; (14)Polarizability: 42.61×10-24cm3; (15)Surface Tension: 60.3 dyne/cm; (16)Density: 1.251 g/cm3; (17)Flash Point: 356.9 °C; (18)Enthalpy of Vaporization: 102.94 kJ/mol; (19)Boiling Point: 666.4 °C at 760 mmHg; (20)Vapour Pressure: 1.14E-18 mmHg at 25°C.
Preparation of Lisinopril: this chemical can be prepared by N2-[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-lysyl-L-proline at the ambient temperature. This reaction will need reagent 1N NaOH with the reaction time of 24 hours. The yield is about 75.8%.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H]2N(C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)CCCCN)CCC2
(2)Std. InChI: InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
(3)Std. InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 6gm/kg (6000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Oyo Yakuri. Pharmacometrics. Vol. 38, Pg. 1, 1989. |
man | LDLo | oral | 43mg/kg/43W-I (43mg/kg) | CARDIAC: PULSE RATE GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Southern Medical Journal. Vol. 87, Pg. 179, 1994. |
man | TDLo | oral | 1mg/kg/2W-I (1mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS | Western Journal of Medicine. Vol. 163, Pg. 77, 1995. |
man | TDLo | oral | 10714ug/kg/21 (10.714mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Netherlands Journal of Medicine. Vol. 46, Pg. 95, 1995. |
mouse | LD50 | intravenous | > 5500mg/kg (5500mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. |
mouse | LD50 | oral | > 9100mg/kg (9100mg/kg) | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. | |
mouse | LD50 | subcutaneous | > 9100mg/kg (9100mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. |
rat | LD50 | intravenous | > 5200mg/kg (5200mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. |
rat | LD50 | oral | > 8500mg/kg (8500mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. |
rat | LD50 | subcutaneous | > 8500mg/kg (8500mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 23, Pg. 2273, 1989. |
women | LDLo | oral | 1200ug/kg/16D (1.2mg/kg) | BLOOD: APLASTIC ANEMIA | Lancet. Vol. 346, Pg. 247, 1995. |
women | TDLo | oral | 60mg/kg/22D (60mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE CARDIAC: CHANGE IN RATE | Lancet. Vol. 1, Pg. 434, 1989. |