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Substance Name: Lisinopril
RN: 76547-98-3
UNII: 7Q3P4BS2FD
InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N

Note

  • One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.

Molecular Formula

  • C21-H31-N3-O5

Molecular Weight

  • 405.492
 

Classification Codes

  • Angiotensin-Converting Enzyme Inhibitors
  • Antihypertensive Agents
  • Cardiotonic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Protease Inhibitors

Names and Synonyms

Results Name

  • Lisinopril

Name of Substance

  • Lisinopril anhydrous
  • Lisinopril [INN]

Synonyms

  • (S)-1-(N(sup 2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline
  • Acerbon
  • Acercomp
  • Alapril
  • Amicor
  • BRN 4276619
  • Carace
  • CCRIS 3568
  • Cipral
  • Cipril
  • Coric
  • Diroton
  • EINECS 278-488-1
  • Hipril
  • HSDB 6852
  • Inhibril
  • Inopril
  • Irumed
  • L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (S)-
  • L-Proline, N2-((1S)-1-carboxy-3-phenylpropyl)-L-lysyl-
  • Laaven
  • Linopril
  • Linvas
  • Lipril
  • Lisinal
  • Lisinopril
  • Lisinoprilum
  • Lisinoprilum [Latin]
  • Lisipril
  • Lisitec
  • Lisopril
  • Lisoril
  • Lispril
  • Listril
  • Lizinopril
  • Lizonoton
  • Longes
  • Loril
  • Lysinopril
  • MK 521
  • MK 522
  • N-(1(S)-Carboxy-3-phenylpropyl)-L-lysyl-L-proline
  • N2-((S)-1-Carboxy-3-phenylpropyl)-L-lysyl-L-proline
  • Nanopril
  • Noperten
  • Novatec
  • Optimon
  • Presiten
  • Prinil
  • Prinivil
  • Prinvil
  • Prinzide
  • Qbrelis
  • Sinopril
  • Sinopryl
  • Skopryl
  • Tensopril
  • Tensyn
  • Tersif
  • UNII-7Q3P4BS2FD
  • Vitopril
  • Vivatec
  • Zestril

Systematic Names

  • (S)-1-(N2-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline
  • L-Proline, 1-(N(sup 2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (S)-
  • L-Proline, N2-((1S)-1-carboxy-3-phenylpropyl)-L-lysyl-
  • Lisinopril

Registry Numbers

CAS Registry Number

  • 76547-98-3

FDA UNII

  • 7Q3P4BS2FD

Related Registry Number

  • 83915-83-7 (Parent)

System Generated Number

  • 0076547983

Structure Descriptors

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

InChIKey

RLAWWYSOJDYHDC-BZSNNMDCSA-N

Smiles

N1([C@@H](CCC1)C(O)=O)C([C@@H](N[C@@H](CCc1ccccc1)C(O)=O)CCCCN)=O

Toxicity

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) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

CARDIAC: PULSE RATE

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS
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) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "JAUNDICE, CHOLESTATIC"
Netherlands Journal of Medicine. Vol. 46, Pg. 95, 1995.
mouse LD50 intravenous > 5500mg/kg (5500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
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): HAIR: OTHER

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
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) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: CHANGE IN RATE
Lancet. Vol. 1, Pg. 434, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.22E+00 (none)   EXP
Water Solubility 13 mg/L 25 EST
Vapor Pressure 3.95E-15 mm Hg 25 EST
Henry's Law Constant 1.89E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.68E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.