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Basic information

  • Name:
  • Lisinopril

  • CAS No.:
  • 76547-98-3

  • Molecular Structure:
  • Formula:
  • C21H31N3O5
  • Molecular Weight:
  • 405.49
  • 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
  • Boiling Point:
  • 666.4 °C at 760 mmHg
  • Flash Point:
  • 356.9 °C
  • Solubility:
  • ≥10 mg/mL in water
  • Appearance:
  • white solid
  • Safety Description:
  • 22-24/25 Details

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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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