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76547-98-3

Basic Information
CAS No.: 76547-98-3
Name: Lisinopril
Article Data: 12
Molecular Structure:
Molecular Structure of 76547-98-3 (Lisinopril)
Formula: C21H31N3O5
Molecular Weight: 405.494
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;
EINECS: 278-488-1
Density: 1.251 g/cm3
Melting Point: 162-165 °C
Boiling Point: 666.4 °C at 760 mmHg
Flash Point: 356.9 °C
Solubility: ≥10 mg/mL in water
Appearance: white solid
Safety: 22-24/25
Synthetic route
103300-91-0

Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

76547-98-3

Lisinopril

Conditions
ConditionsYield
With water; sodium hydroxide at 40 - 45℃; pH=12 - 13;92%
85955-58-4

N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

76547-98-3

Lisinopril

Conditions
ConditionsYield
With sodium hydroxide for 24h; Ambient temperature;75.8%
77726-95-5

(S)-1-[N2-(1-carboxy-3-phenylpropyl]-L-lysyl]-L-proline

A

76547-98-3

Lisinopril

B

85955-59-5

lisinopril

Conditions
ConditionsYield
With hydrogenchloride In water Resolution of racemate;A 75%
B n/a
710-11-2

2-oxo-4-phenylbutyric acid

4583-24-8

H-Lys(Boc)-Pro-OH

A

76547-98-3

Lisinopril

B

85955-59-5

lisinopril

Conditions
ConditionsYield
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;
103300-91-0

Nε-(trifluoroacetyl)-Nα-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline

A

76547-98-3

Lisinopril

B

85955-59-5

lisinopril

Conditions
ConditionsYield
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;
120095-49-0

N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

76547-98-3

Lisinopril

Conditions
ConditionsYield
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

(S)-1-[(S)-6-tert-Butoxycarbonylamino-2-((R)-1-carboxy-3-oxo-3-phenyl-propylamino)-hexanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester; compound with (Z)-but-2-enedioic acid

76547-98-3

Lisinopril

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
16652-71-4, 53843-90-6, 80089-24-3

L-proline benzyl ester hydrochloride

76547-98-3

Lisinopril

Conditions
ConditionsYield
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
90826-23-6

N-(N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester

76547-98-3

Lisinopril

Conditions
ConditionsYield
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

N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-L-lysine

76547-98-3

Lisinopril

Conditions
ConditionsYield
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
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History

   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. 

Specification

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%.

Lisinopril can be prepared by N2-[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-lysyl-L-proline at the ambient temperature

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.