Benazepril

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Benazepril
Benazepril.svg
Systematic (IUPAC) name
2-[(3S)-3-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-
Clinical data
Trade names Lotensin
AHFS/Drugs.com monograph
MedlinePlus a692011
Pregnancy cat. D
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Protein binding 96.7%
Metabolism Hepatic glucuronidation
Half-life 10-11 hours
Excretion Renal and biliary
Identifiers
CAS number 86541-75-5 YesY
ATC code C09AA07
PubChem CID 5362124
DrugBank DB00542
ChemSpider 4514935 YesY
UNII UDM7Q7QWP8 YesY
ChEBI CHEBI:3011 YesY
ChEMBL CHEMBL838 YesY
Chemical data
Formula C24H28N2O5 
Mol. mass 424.49 g/mol
 YesY (what is this?)  (verify)

Benazepril, brand name Lotensin (Novartis), is a drug of the angiotensin-converting enzyme (ACE) inhibitor class used primarily in treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing renal and retinal complications of diabetes. Its indications, contraindications and side effects are as those for all ACE inhibitors. The drug is a precursor of the active agent, which is metabolized by the liver into its active form. Upon cleavage of its ester group benazepril is converted into benazeprilat, its active form, which is a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor.

Dosage forms[edit]

Benazepril is available as oral tablets, in 5-, 10-, 20-, and 40-mg doses.

Benazepril is also available in combination with hydrochlorothiazide, under the trade name Lotensin HCT, and with amlodipine (trade name Lotrel).

Side effects[edit]

The most common side effects patients experience are headaches or a chronic cough. The chronic cough develops in about 20 percent of patients treated,[1] and those patients that experience it find it develops after a couple of months of use. Anaphylaxis, angioedema and hyperkalemia, the elevation of potassium levels, are more serious side effects that can also occur.

Benazepril may cause harm to the fetus during pregnancy.

Contraindications[edit]

Benazepril should be discontinued during pregnancy.

Kidney disease[edit]

According to a 2006 article in the New England Journal of Medicine, patients with advanced renal insufficiency taking benazepril showed "substantial" kidney benefits.[2]

A long-term study of patients' kidney disease revealed patients who took benazepril had better kidney function and slower progressions of kidney disease than their peers who took a placebo drug.[3] This is notable because this category of pharmaceuticals has long been thought to cause further kidney damage or increase the rate of progression for kidney disease.

According to coverage of the study on WebMD:

ACE inhibitors can pose a potential threat to kidneys as well. The key question was whether damaged kidneys would worsen if patients took ACE inhibitors. In a nutshell, concerns centered on blood levels of potassium and creatinine, waste products that are excreted by the kidneys. Testing creatinine levels in the blood is used as a way to monitor kidney function (...) kidney problems worsened more slowly in those taking Lotensin. Overall, there were no major differences in side effects between patients taking Lotensin or the placebo.[3]

This study marks the first indication that benazepril, and perhaps other ACE inhibitors, may actually be beneficial in the treatment of hypertension in patients with kidney disease.

Veterinary use[edit]

Under the brand names Fortekor (Novartis) and VetACE (Jurox Animal Health),[citation needed] benazepril hydrochloride is used to treat congestive heart failure in dogs[4][5] and chronic renal failure in dogs and cats.[citation needed]

Synthesis[edit]

Benazepril synthesis 1.[6]
Benazepril synthesis 2.[6]

References[edit]

  1. ^ Dykewicz, Mark S. (April 2004). "Cough and Angioedema From Angiotensin-Converting Enzyme Inhibitors: New Insights Into Mechanisms and Management". Medscape. Retrieved 2 April 2014. 
  2. ^ Hou F, Zhang X, Zhang G, Xie D, Chen P, Zhang W, Jiang J, Liang M, Wang G, Liu Z, Geng R (2006). "Efficacy and safety of benazepril for advanced chronic renal insufficiency". N Engl J Med 354 (2): 131–40. doi:10.1056/NEJMoa053107. PMID 16407508. 
  3. ^ a b Hitti, Miranda; Chang, Louise (January 11, 2006). "Drug May Treat Advanced Kidney Disease". WebMD. Retrieved 2006-09-07. 
  4. ^ King JN, Mauron C, Kaiser G (December 1995). "Pharmacokinetics of the active metabolite of benazepril, benazeprilat, and inhibition of plasma angiotensin-converting enzyme activity after single and repeated administrations to dogs". Am. J. Vet. Res. 56 (12): 1620–8. PMID 8599524. 
  5. ^ O'Grady MR, O'Sullivan ML, Minors SL, Horne R (2009). "Efficacy of benazepril hydrochloride to delay the progression of occult dilated cardiomyopathy in Doberman Pinschers". J. Vet. Intern. Med. 23 (5): 977–83. doi:10.1111/j.1939-1676.2009.0346.x. PMID 19572914. 
  6. ^ a b http://drugsynthesis.blogspot.co.uk/2012/05/laboratory-synthesis-of-benazepril.html

External links[edit]