Lisinopril supplier | CasNO.76547-98-3

Name
Lisinopril
EINECS 278-488-1
CAS No. 76547-98-3
Article Data12
CAS DataBase
Density 1.251 g/cm³
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
Appearance white solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA
LogP

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

: 19522-26-0
3-benzoyl-2-propenoic acid

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triethylamine / 1.) 5 h, RT, benzene; 2.) ethylacetate 2: H2 / Pd/C View Scheme

: 17812-07-6
Benzoylacrylic acid

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triethylamine / 1.) 5 h, RT, benzene; 2.) ethylacetate 2: H2 / Pd/C View Scheme

: 32489-85-3
L-Lys(Boc)-L-Pro-OBut

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triethylamine / 1.) 5 h, RT, benzene; 2.) ethylacetate 2: H2 / Pd/C View Scheme
Multi-step reaction with 2 steps 1: 1.) triethylamine / 1.) 5 h, RT, benzene; 2.) ethylacetate 2: H2 / Pd/C View Scheme

: 104-53-0
3-phenyl-propionaldehyde

sodium-: sodium-

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 45 percent / methanol; H2O / 8 h / 70 °C 2: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9 3: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 4: 95 percent / SOCl2 / 24 h / Ambient temperature 5: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 6: 89 percent / TFA / 24 h / Ambient temperature 7: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 45 percent / methanol; H2O / 8 h / 70 °C
2: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9
3: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h
4: 95 percent / SOCl2 / 24 h / Ambient temperature
5: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C
6: 89 percent / TFA / 24 h / Ambient temperature
7: 75.8 percent / 1N NaOH / 24 h / Ambient temperature
View Scheme

: 120379-81-9
5-phenylethyl-imidazolidine-2,4-dione

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9 2: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 3: 95 percent / SOCl2 / 24 h / Ambient temperature 4: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 5: 89 percent / TFA / 24 h / Ambient temperature 6: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9
2: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h
3: 95 percent / SOCl2 / 24 h / Ambient temperature
4: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C
5: 89 percent / TFA / 24 h / Ambient temperature
6: 75.8 percent / 1N NaOH / 24 h / Ambient temperature
View Scheme

: 121842-76-0
(R)-2-bromo-4-phenylbutyric acid

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / SOCl2 / 24 h / Ambient temperature 2: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 3: 89 percent / TFA / 24 h / Ambient temperature 4: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

: 121842-77-1
(R)-ethyl 2-bromo-4-phenylbutyrate

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 2: 89 percent / TFA / 24 h / Ambient temperature 3: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

: 121842-75-9
N-carbamyl (R)-2-amino-4-phenylbutyric acid

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 2: 95 percent / SOCl2 / 24 h / Ambient temperature 3: 70 percent / (NH4)2CO3 / H2O; nitromethane / 96 h / 50 °C 4: 89 percent / TFA / 24 h / Ambient temperature 5: 75.8 percent / 1N NaOH / 24 h / Ambient temperature View Scheme

: 710-11-2
2-oxo-4-phenylbutyric acid

: 76547-98-3
Lisinopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) molecular sieves, sodium acetate, catecholborane / 1.) CH2Cl2, -15 - 0 deg C, 1 h.; 2.) CH2Cl2 2: 1.) TFA; 2.) 1M NaOH View Scheme

: 64-17-5
ethanol

: 76547-98-3
Lisinopril

: 877865-60-6
lisinopril diethyl ester

Conditions

Conditions	Yield
With thionyl chloride for 3h; Reflux;	100%
Stage #1: ethanol; Lisinopril With thionyl chloride for 5.5h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water

: 76547-98-3
Lisinopril

: N-{N-[(S)-1-cyclohexylcarboxy-3-propyl]-L-lysyl}-L-proline

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen; acetic acid In methanol at 30℃; under 1292.9 - 1551.49 Torr; for 48h; Solvent; Temperature;	75%

: zinc perchlorate

: 7732-18-5
water

: 76547-98-3
Lisinopril

: 4C21H29N3O5(2-)*4Zn(2+)*16H2O

Conditions

Conditions	Yield
With triethylamine In methanol at 79.84℃; for 38h; High pressure;	60%

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 76547-98-3
Lisinopril

: (S)-1-[(S)-6-Amino-2-((S)-1-methoxycarbonyl-3-phenyl-propylamino)-hexanoyl]-pyrrolidine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In methanol; diethyl ether at 5 - 10℃; for 0.5h;

: 31469-89-3
4-azido-2,3,5,6-tetrafluorobenzonitrile

: 76547-98-3
Lisinopril

: (S)-1-{(S)-6-Amino-2-[N-((S)-1-carboxy-3-phenyl-propyl)-N'-(4-cyano-2,3,5,6-tetrafluoro-phenyl)-hydrazino]-hexanoyl}-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
In d(4)-methanol Irradiation;

: 126695-58-7
succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate

: 76547-98-3
Lisinopril

: (S)-1-[(S)-6-(4-Azido-2,3,5,6-tetrafluoro-benzoylamino)-2-((S)-1-carboxy-3-phenyl-propylamino)-hexanoyl]-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide

: 76547-98-3
Lisinopril

: 197070-57-8
C11H14F4N7O4P

: C32H45F4N8O9P

Conditions

Conditions	Yield
In d(4)-methanol Irradiation;

: 76547-98-3
Lisinopril

: 141762-27-8
N-succinimidyl 4-[18F]fluorobenzoate

: 4-[18F]fluorobenzoyllisinopril

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 0.25h;

: 76547-98-3
Lisinopril

: C21H29(3)H2N3O5

Conditions

Conditions	Yield
Stage #1: Lisinopril With N-Bromosuccinimide; sulfuric acid at 65℃; for 2h; Stage #2: With hydrogen; triethylamine; palladium/alumina In methanol at 20℃;

: 24424-99-5
di-tert-butyl dicarbonate

: 76547-98-3
Lisinopril

: 121-44-8
triethylamine

: 811788-06-4
(S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl(boc)]-L-proline

Conditions

Conditions	Yield
In 1,4-dioxane; water at 0 - 20℃;

...Expand

Lisinopril 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.

Lisinopril 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.

Product Name

Lisinopril

Synthetic route

Lisinopril History

Lisinopril Specification

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