Lisinopril
Identification
- Name
- Lisinopril
- Accession Number
- DB00722 (APRD00560)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Lisinopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Lisinopril may be used to treat hypertension and symptomatic congestive heart failure, to improve survival in certain individuals following myocardial infarction, and to prevent progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy.
- Structure
Structure for Lisinopril (DB00722)
- Synonyms
- (S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline
- [N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline
- Lisinopril
- Lisinopril anhydrous
- Lisinoprilum
- Product Ingredients
Ingredient UNII CAS InChI Key Lisinopril dihydrate E7199S1YWR 83915-83-7 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Act Lisinopril Tablet 10 mg Oral Actavis Pharma Company 2007-10-17 Not applicable Canada 
Act Lisinopril Tablet 20 mg Oral Actavis Pharma Company 2007-10-17 Not applicable Canada Act Lisinopril Tablet 5 mg Oral Actavis Pharma Company 2007-10-17 Not applicable Canada Lisinopril Tablet 5 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Lisinopril Tablet 20 mg/1 Oral Lek Pharmaceuticals 2007-03-02 Not applicable US 
Lisinopril Tablet 5 mg Oral Meliapharm Inc 2008-03-12 2014-06-25 Canada Lisinopril Tablet 30 mg/1 Oral West-ward Pharmaceutical Corp. 2008-08-28 2008-08-28 US Lisinopril Tablet 5 mg/1 Oral Lek Pharmaceuticals 2007-03-02 Not applicable US Lisinopril Tablet 20 mg Oral Sivem Pharmaceuticals Ulc 2012-06-11 Not applicable Canada Lisinopril Tablet 10 mg Oral Sorres Pharma Inc 2009-06-22 2014-06-20 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Apo-lisinopril Tablet (type P) - 10mg Tablet 10 mg Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 20mg Tablet 20 mg Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 40mg Tablet 40 mg Oral Apotex Corporation 1996-12-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 5mg Tablet 5 mg Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet 10 mg Tablet 10 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 20 mg Tablet 20 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 40 mg Tablet 40 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 5 mg Tablet 5 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Auro-lisinopril Tablet 10 mg Oral Auro Pharma Inc 2013-02-12 Not applicable Canada Auro-lisinopril Tablet 20 mg Oral Auro Pharma Inc 2013-02-12 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Apo-lisinopril/hctz Lisinopril (20 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Apotex Corporation 2007-11-21 Not applicable Canada Apo-lisinopril/hctz Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Apotex Corporation 2007-09-05 Not applicable Canada Apo-lisinopril/hctz Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Apotex Corporation 2007-11-21 Not applicable Canada Ava-lisinopril Hct Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Ava-lisinopril Hct Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Ava-lisinopril Hct Lisinopril (20 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Lisinopril and HCTZ Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Northwind Pharmaceuticals 2014-07-10 Not applicable US 
Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral Teva 2010-06-30 2010-06-30 US Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral Med Pharma Co., Ltd. 2011-07-10 2012-07-31 US Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral Med Vantx, Inc. 2002-07-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Lytensopril Lisinopril dihydrate (20 mg/1) + L-Arginine (60 mg/1) Kit Physician Therapeutics Llc 2011-07-07 Not applicable US Lytensopril-90 Lisinopril dihydrate (20 mg/1) + L-Arginine (90 mg/1) Kit Physician Therapeutics Llc 2011-07-07 Not applicable US - International/Other Brands
- Acebitor (GlaxoSmithKline) / Acemin (AstraZeneca) / Acerbon (AstraZeneca) / Acinopril (sanofi-aventis) / Bellisin (Ranbaxy) / Biopril (Biochem) / Dapril (Medochemie) / Fibsol (Sigma) / Fisopril (Sanofi-Aventis) / Hipril (Micro Labs) / Linopril (Klinger (Brazil)) / Lisipril (Hexal (Czech Republic), Orion (Finland)) / Noperten (Dexa (Indonesia)) / Presiten (Magnachem) / Ranolip (Ranbaxy) / Ranopril (Ranbaxy) / Rantex (Biotech) / Sinopren (Ranbaxy) / Sinopril (Eczacibasi (Russia)) / Tensopril (Merck)
- Categories
- ACE Inhibitors and Calcium Channel Blockers
- ACE Inhibitors and Diuretics
- Agents Acting on the Renin-Angiotensin System
- Agents causing angioedema
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amino Acids, Peptides, and Proteins
- Angiotensin-Converting Enzyme Inhibitors
- Antihypertensive Agents
- Cardiotonic Agents
- Cardiovascular Agents
- Dipeptides
- Enzyme Inhibitors
- Hypotensive Agents
- Lipid Modifying Agents
- Oligopeptides
- Peptides
- Protease Inhibitors
- Protective Agents
- UNII
- 7Q3P4BS2FD
- CAS number
- 76547-98-3
- Weight
- Average: 405.4879
Monoisotopic: 405.226371117 - Chemical Formula
- C21H31N3O5
- InChI Key
- RLAWWYSOJDYHDC-BZSNNMDCSA-N
- 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
- IUPAC Name
- (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
- SMILES
- NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
Pharmacology
- Indication
For the treatment of hypertension and symptomatic congestive heart failure. May be used in conjunction with thrombolytic agents, aspirin and/or β-blockers to improve survival in hemodynamically stable individuals following myocardial infarction. May be used to slow the progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy.
- Associated Conditions
- Pharmacodynamics
Lisinopril is an orally active ACE inhibitor that antagonizes the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may further sustain the effects of lisinopril by causing increased vasodilation and decreased blood pressure.
- Mechanism of action
There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Lisinopril, one of the few ACE inhibitors that is not a prodrug, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Lisinopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.
Target Actions Organism AAngiotensin-converting enzyme inhibitorHumans - Absorption
Approximately 25%, but widely variable between individuals (6 to 60%) in all doses tested (5-80 mg); absorption is unaffected by food
- Volume of distribution
- Not Available
- Protein binding
Lisinopril does not appear to be bound to serum proteins other than ACE.
- Metabolism
Does not undergo metabolism, excreted unchanged in urine.
- Route of elimination
Lisinopril does not undergo metabolism and is excreted unchanged entirely in the urine.
- Half life
Effective half life of accumulation following multiple dosing is 12 hours.
- Clearance
- 10 L/h [child weighting 30 kg receiving doses of 0.1 to 0.2 mg/kg]
- Toxicity
Symptoms of overdose include severe hypotension, electrolyte disturbances, and renal failure. LD50= 2000 mg/kg(orally in rat). Most frequent adverse effects include headache, dizziness, cough, fatigue and diarrhea.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Lisinopril Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid Lisinopril may increase the hypotensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid. 1-benzylimidazole The risk or severity of hypertension can be increased when Lisinopril is combined with 1-benzylimidazole. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of hypertension can be increased when Lisinopril is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of hypertension can be increased when Lisinopril is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine The risk or severity of hypertension can be increased when Lisinopril is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of hypertension can be increased when Lisinopril is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of hypertension can be increased when Lisinopril is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of hypertension can be increased when Lisinopril is combined with 5-methoxy-N,N-dimethyltryptamine. Abacavir Lisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level. Abediterol The risk or severity of hypertension can be increased when Lisinopril is combined with Abediterol. - Food Interactions
- Herbs that may attenuate the antihypertensive effect of lisinopril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
- High salt intake may attenuate the antihypertensive effect of lisinopril.
- Lisinopril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.
- Take without regard to meals.
References
- Synthesis Reference
Vincenzo Cannata, Valeriano Merli, Stefano Saguatti, "Process for the production of alkoxycarbonyldipeptides intermediates in the synthesis of the lisinopril." U.S. Patent US6166217, issued September, 1972.
US6166217- General References
- Abdelmalek MF, Douglas DD: Lisinopril-induced isolated visceral angioedema: review of ACE-inhibitor-induced small bowel angioedema. Dig Dis Sci. 1997 Apr;42(4):847-50. [PubMed:9125659]
- Hasslacher C: Influence of the ACE inhibitor lisinopril on blood pressure, metabolism, and renal function parameter in hypertensive type II diabetic patients: a postmarketing surveillance study. J Diabetes Complications. 1996 May-Jun;10(3):136-8. [PubMed:8807458]
- Nielsen SE, Sugaya T, Tarnow L, Lajer M, Schjoedt KJ, Astrup AS, Baba T, Parving HH, Rossing P: Tubular and glomerular injury in diabetes and the impact of ACE inhibition. Diabetes Care. 2009 Sep;32(9):1684-8. doi: 10.2337/dc09-0429. Epub 2009 Jun 5. [PubMed:19502542]
- Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3. [PubMed:6253826]
- External Links
- Human Metabolome Database
- HMDB0001938
- KEGG Drug
- D00362
- PubChem Compound
- 5362119
- PubChem Substance
- 46504893
- ChemSpider
- 4514933
- BindingDB
- 50367879
- ChEBI
- 43755
- ChEMBL
- CHEMBL1237
- Therapeutic Targets Database
- DAP000587
- PharmGKB
- PA450242
- HET
- LPR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Lisinopril
- ATC Codes
- C09BA03 — Lisinopril and diuretics
- C09BA — ACE inhibitors and diuretics
- C09B — ACE INHIBITORS, COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- C10BX — HMG CoA reductase inhibitors, other combinations
- C10B — LIPID MODIFYING AGENTS, COMBINATIONS
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C09AA — ACE inhibitors, plain
- C09A — ACE INHIBITORS, PLAIN
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- AHFS Codes
- 24:32.04 — Angiotensin-converting Enzyme Inhibitors
- PDB Entries
- 1j36 / 1o86 / 2c6n / 2x91
- FDA label
- Download (267 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Actavis elizabeth llc
- Apotex inc etobicoke site
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- Teva pharmaceuticals usa inc
- Vintage pharmaceuticals llc
- Watson laboratories inc
- West ward pharmaceutical corp
- Wockhardt ltd
- Merck research laboratories div merck co inc
- Astrazeneca uk ltd
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- Dosage forms
Form Route Strength Tablet Oral 40 mg Tablet Oral 5 mg Tablet Oral 10 1/1 Tablet Oral 10 mg/1 Tablet Oral 10 mg/301 Tablet Oral 2.5 mg/1 Tablet Oral 20 mg/1 Tablet Oral 30 mg/1 Tablet Oral 40 mg/1 Tablet Oral 5 mg/1 Tablet Oral 5.0 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 2.5 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 30 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 5 mg/1 Kit Tablet Oral 10 mg Tablet Oral 2.5 mg Tablet Oral 20 mg Solution Oral 1 mg/1mL Tablet Oral - Prices
Unit description Cost Unit Prinivil 90 20 mg tablet Bottle 111.71USD bottle Prinzide 30 20-12.5 mg tablet Bottle 45.99USD bottle Prinivil 30 2.5 mg tablet Bottle 22.48USD bottle Lisinopril 100% powder 21.6USD g Zestril 40 mg tablet 2.53USD tablet Zestril 30 mg tablet 2.41USD tablet Prinivil 40 mg tablet 2.23USD tablet Zestoretic 20-25 mg tablet 2.01USD tablet Zestoretic 20-12.5 mg tablet 2.0USD tablet Prinzide 20-25 mg tablet 1.98USD tablet Zestoretic 10-12.5 mg tablet 1.89USD tablet Zestoretic 10-12.5 tablet 1.75USD tablet Lisinopril 30 mg tablet 1.53USD tablet Lisinopril 40 mg tablet 1.44USD tablet Prinzide 20-12.5 mg tablet 1.38USD tablet Prinzide 10-12.5 mg tablet 1.37USD tablet Zestril 20 mg tablet 1.37USD tablet Zestril 10 mg tablet 1.33USD tablet Zestoretic 20-25 tablet 1.28USD tablet Zestril 5 mg tablet 1.28USD tablet Zestoretic 20-12.5 tablet 1.26USD tablet Lisinopril 20 mg tablet 1.09USD tablet Prinivil 20 mg tablet 1.05USD tablet Zestril 2.5 mg tablet 1.04USD tablet Lisinopril 10 mg tablet 1.01USD tablet Prinivil 10 mg tablet 1.01USD tablet Lisinopril 5 mg tablet 0.99USD tablet Prinivil 5 mg tablet 0.96USD tablet Apo-Lisinopril 20 mg Tablet 0.71USD tablet Co Lisinopril 20 mg Tablet 0.71USD tablet Mylan-Lisinopril 20 mg Tablet 0.71USD tablet Novo-Lisinopril (Type P) 20 mg Tablet 0.71USD tablet Novo-Lisinopril (Type Z) 20 mg Tablet 0.71USD tablet Pms-Lisinopril 20 mg Tablet 0.71USD tablet Ran-Lisinopril 20 mg Tablet 0.71USD tablet Ratio-Lisinopril P 20 mg Tablet 0.71USD tablet Ratio-Lisinopril Z 20 mg Tablet 0.71USD tablet Sandoz Lisinopril 20 mg Tablet 0.71USD tablet Lisinopril 2.5 mg tablet 0.65USD tablet Apo-Lisinopril 10 mg Tablet 0.59USD tablet Co Lisinopril 10 mg Tablet 0.59USD tablet Mylan-Lisinopril 10 mg Tablet 0.59USD tablet Novo-Lisinopril (Type P) 10 mg Tablet 0.59USD tablet Novo-Lisinopril (Type Z) 10 mg Tablet 0.59USD tablet Pms-Lisinopril 10 mg Tablet 0.59USD tablet Ran-Lisinopril 10 mg Tablet 0.59USD tablet Ratio-Lisinopril P 10 mg Tablet 0.59USD tablet Ratio-Lisinopril Z 10 mg Tablet 0.59USD tablet Sandoz Lisinopril 10 mg Tablet 0.59USD tablet Apo-Lisinopril 5 mg Tablet 0.49USD tablet Co Lisinopril 5 mg Tablet 0.49USD tablet Mylan-Lisinopril 5 mg Tablet 0.49USD tablet Novo-Lisinopril (Type P) 5 mg Tablet 0.49USD tablet Novo-Lisinopril (Type Z) 5 mg Tablet 0.49USD tablet Pms-Lisinopril 5 mg Tablet 0.49USD tablet Ran-Lisinopril 5 mg Tablet 0.49USD tablet Ratio-Lisinopril P 5 mg Tablet 0.49USD tablet Ratio-Lisinopril Z 5 mg Tablet 0.49USD tablet Sandoz Lisinopril 5 mg Tablet 0.49USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US9463183 No 2016-10-11 2035-11-06 US US9616096 No 2017-04-11 2035-11-06 US US9814751 No 2017-11-14 2035-11-06 US US10039800 No 2015-11-06 2035-11-06 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 9.7E+004 mg/L MERCK INDEX (1996) logP -1.01 MERCK INDEX (1996); pH 7 pKa 2.5 (at 25 °C) MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.216 mg/mL ALOGPS logP -1.2 ALOGPS logP -3.1 ChemAxon logS -3.3 ALOGPS pKa (Strongest Acidic) 3.17 ChemAxon pKa (Strongest Basic) 10.21 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 132.96 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 107.37 m3·mol-1 ChemAxon Polarizability 43.5 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.6426 Blood Brain Barrier - 0.8815 Caco-2 permeable - 0.7605 P-glycoprotein substrate Substrate 0.6515 P-glycoprotein inhibitor I Non-inhibitor 0.9512 P-glycoprotein inhibitor II Non-inhibitor 0.969 Renal organic cation transporter Non-inhibitor 0.8574 CYP450 2C9 substrate Non-substrate 0.8793 CYP450 2D6 substrate Non-substrate 0.7622 CYP450 3A4 substrate Non-substrate 0.725 CYP450 1A2 substrate Non-inhibitor 0.8999 CYP450 2C9 inhibitor Non-inhibitor 0.9708 CYP450 2D6 inhibitor Non-inhibitor 0.9653 CYP450 2C19 inhibitor Non-inhibitor 0.8266 CYP450 3A4 inhibitor Non-inhibitor 0.907 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9821 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9389 Biodegradation Not ready biodegradable 0.6844 Rat acute toxicity 1.8723 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9641 hERG inhibition (predictor II) Non-inhibitor 0.8708
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides show 9 more
- Substituents
- Alpha-dipeptide / N-acyl-alpha-amino acid / Proline or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / N-acylpyrrolidine show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- dipeptide (CHEBI:43755)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
- Gene Name
- ACE
- Uniprot ID
- P12821
- Uniprot Name
- Angiotensin-converting enzyme
- Molecular Weight
- 149713.675 Da
References
- Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016]
- Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321]
- Tellez-Sanz R, Garcia-Fuentes L, Baron C: Calorimetric analysis of lisinopril binding to angiotensin I-converting enzyme. FEBS Lett. 1998 Feb 13;423(1):75-80. [PubMed:9506845]
Drug created on June 13, 2005 07:24 / Updated on January 22, 2019 17:56