Name: Lisinopril
SKU: 76547-98-3

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Basic Information

Molecular Structure:
CAS No.:	76547-98-3
Name:	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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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;

...Expand

: 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

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;

: 120095-49-0
N6-(tert-butoxycarbonyl)-N2-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-lysyl-L-proline tert-butylester

: 76547-98-3
Lisinopril

Conditions

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

: (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

Conditions	Yield
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

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

: 90826-23-6
N-(N2-benzyloxycarbonyl-N6-tert-butoxycarbonyl-L-lysyl)-L-proline benzyl ester

: 76547-98-3
Lisinopril

Conditions

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

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

: 76547-98-3
Lisinopril

Conditions

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

Raw Materials

710-11-2

104-53-0

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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.

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