Benazepril

Last updated

Benazepril
Benazepril structure.svg
Benazepril-3D-balls.png
Clinical data
Pronunciation /bəˈnæzəprɪl/
Trade names Lotensin, others
AHFS/Drugs.com Monograph
MedlinePlus a692011
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding 96.7%
Metabolism Liver glucuronidation
Elimination half-life 10-11 hours
Excretion Kidney and bile duct
Identifiers
  • 2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H28N2O5
Molar mass 424.497 g·mol−1
3D model (JSmol)
  • O=C(OCC)[C@@H](N[C@@H]2C(=O)N(c1ccccc1CC2)CC(=O)O)CCc3ccccc3
  • InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1 Yes check.svgY
  • Key:XPCFTKFZXHTYIP-PMACEKPBSA-N Yes check.svgY
   (verify)

Benazepril, sold under the brand name Lotensin among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. [1] It is a reasonable initial treatment for high blood pressure. [1] It is taken by mouth. [1] Versions are available as the combinations benazepril/hydrochlorothiazide and benazepril/amlodipine. [1]

Contents

Common side effects include feeling tired, dizziness, cough, and light-headedness with standing. [1] Serious side effects may include kidney problems, low blood pressure, high blood potassium, and angioedema. [1] Use in pregnancy may harm the baby, while use when breastfeeding may be safe. [2] It is an ACE inhibitor and works by decreasing renin-angiotensin-aldosterone system activity. [1]

Benazepril was patented in 1981 and came into medical use in 1990. It was created by the chemist Mahesh Desai. [3] It is available as a generic medication. [1] In 2020, it was the 141st most commonly prescribed medication in the United States, with more than 4 million prescriptions. [4] [5]

Structure activity relationship

Benazepril hydrochloride's OCH2CH3 group must be metabolized to form benazeprilat—the active form of the molecule—in order to inhibit the ACE enzyme. The bulky cyclic structure is resistant to hydrolysis. The nitrogen within the ring makes the bulky cyclic structure especially difficult to break down, and can account for the drug's pharmacokinetic profile, in which the duration of action is 24 hours.[ medical citation needed ]

Medical uses

It is useful for high blood pressure, heart failure, and diabetic kidney disease. [1] It is a reasonable initial treatment for high blood pressure. [1] Other reasonable initial options include angiotensin II receptor antagonists, calcium-channel blockers, and thiazide diuretics. [1]

Side effects

The most common side effects patients experience are a headache or a chronic cough. The chronic cough develops in about 20% of patients treated, [6] and those patients that experience it find it develops after a few months of use. Anaphylaxis, angioedema, and elevation of potassium levels are more serious side effects that can also occur.

Contraindications

Benazepril should be discontinued during pregnancy and in women planning to become pregnant, as it can harm the fetus. [7]

Dosage forms

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

Veterinary use

Under the brand names Fortekor (Novartis) and VetACE (Jurox Animal Health),[ citation needed ] benazepril is used to treat congestive heart failure in dogs [8] [9] and chronic kidney failure in cats and dogs. [10]

Related Research Articles

<span class="mw-page-title-main">ACE inhibitor</span> Class of medications used primarily to treat high blood pressure

Angiotensin-converting-enzyme inhibitors are a class of medication used primarily for the treatment of high blood pressure and heart failure. This class of medicine works by causing relaxation of blood vessels as well as a decrease in blood volume, which leads to lower blood pressure and decreased oxygen demand from the heart.

Antihypertensives are a class of drugs that are used to treat hypertension. Antihypertensive therapy seeks to prevent the complications of high blood pressure, such as stroke, heart failure, kidney failure and myocardial infarction. Evidence suggests that reduction of the blood pressure by 5 mmHg can decrease the risk of stroke by 34% and of ischaemic heart disease by 21%, and can reduce the likelihood of dementia, heart failure, and mortality from cardiovascular disease. There are many classes of antihypertensives, which lower blood pressure by different means. Among the most important and most widely used medications are thiazide diuretics, calcium channel blockers, ACE inhibitors, angiotensin II receptor antagonists (ARBs), and beta blockers.

<span class="mw-page-title-main">Amlodipine</span> Dihydropyridine calcium channel blocker used to treat cardiovascular diseases

Amlodipine, sold under the brand name Norvasc among others, is a calcium channel blocker medication used to treat high blood pressure, coronary artery disease (CAD) and variant angina. It is taken orally.

<span class="mw-page-title-main">Enalapril</span> ACE inhibitor medication

Enalapril, sold under the brand name Vasotec among others, is an ACE inhibitor medication used to treat high blood pressure, diabetic kidney disease, and heart failure. For heart failure, it is generally used with a diuretic, such as furosemide. It is given by mouth or by injection into a vein. Onset of effects are typically within an hour when taken by mouth and last for up to a day.

<span class="mw-page-title-main">Fosinopril</span> Antihypertensive drug of the ACE inhibitor class

Fosinopril is an angiotensin converting enzyme (ACE) inhibitor used for the treatment of hypertension and some types of chronic heart failure. Fosinopril is the only phosphonate-containing ACE inhibitor marketed, by Bristol-Myers Squibb under the trade name Monopril. Fosinopril is a cascading pro-drug. The special niche for the medication that differentiates it from the other members of the ACE Inhibitor drug class is that was specifically developed for the use for patients with renal impairment. This was through manipulation of the metabolism and excretion, and is seen that fifty percent of the drug is hepatobiliary cleared, which can compensate for diminished renal clearance. The remaining fifty percent is excreted in urine. It does not need dose adjustment.

<span class="mw-page-title-main">Irbesartan</span> Chemical compound

Irbesartan, sold under the brand name Avapro among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination irbesartan/hydrochlorothiazide.

<span class="mw-page-title-main">Lisinopril</span> Medication used to treat high blood pressure and heart failure

Lisinopril is a medication belonging to the drug class of angiotensin-converting enzyme (ACE) inhibitors and is used to treat high blood pressure, heart failure, and heart attacks. For high blood pressure it is usually a first-line treatment. It is also used to prevent kidney problems in people with diabetes mellitus. Lisinopril is taken by mouth. Full effect may take up to four weeks to occur.

<span class="mw-page-title-main">Ramipril</span> ACE inhibitor

Ramipril, sold under the brand name Altace among others, is an ACE inhibitor type medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It can also be used as a preventative medication in patients over 55 years old to reduce the risk of having a heart attack, stroke or cardiovascular death in patients shown to be at high risk, such as some diabetics and patients with vascular disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth.

<span class="mw-page-title-main">Quinapril</span> ACE inhibitor used in the treatment of hypertension and congestive heart failure

Quinapril, sold under the brand name Accupril by the Pfizer corporation. It a medication used to treat high blood pressure (hypertension), heart failure, and diabetic kidney disease. It is a first line treatment for high blood pressure. It is taken by mouth.

<span class="mw-page-title-main">Telmisartan</span> Angiotensin II receptor antagonist

Telmisartan, sold under the brand name Micardis among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination telmisartan/hydrochlorothiazide, telmisartan/cilnidipine and telmisartan/amlodipine.

<span class="mw-page-title-main">Losartan</span> Blood pressure medication

Losartan, sold under the brand name Cozaar among others, is a medication used to treat high blood pressure (hypertension). It is in the angiotensin receptor blocker (ARB) family of medication, and is considered protective of the kidneys. Besides hypertension, it is also used in diabetic kidney disease, heart failure, and left ventricular enlargement. It comes as a tablet that is taken by mouth. It may be used alone or in addition to other blood pressure medication. Up to six weeks may be required for the full effects to occur.

<span class="mw-page-title-main">Valsartan</span> Angiotensin II receptor antagonist

Valsartan, sold under the brand name Diovan among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It belongs to a class of medications referred to as angiotensin II receptor blockers (ARBs). It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination valsartan/hydrochlorothiazide, valsartan/amlodipine, valsartan/amlodipine/hydrochlorothiazide, or valsartan/sacubitril.

<span class="mw-page-title-main">Olmesartan</span> Angiotensin II receptor antagonist

Olmesartan, sold under the brand name Benicar among others, is a medication used to treat high blood pressure (hypertension). It is taken by mouth. Versions are available as the combination olmesartan/hydrochlorothiazide and olmesartan/amlodipine.

Lisinopril/hydrochlorothiazide, sold under the brand name Zestoretic among others, is a fixed-dose combination medication used for the treatment of high blood pressure. It contains lisinopril, an ACE inhibitor, and hydrochlorothiazide, a diuretic. Typically, it becomes an option once a person is doing well on the individual components. It is taken by mouth.

<span class="mw-page-title-main">Amlodipine/benazepril</span> Antihypertensive medication

Amlodipine/benazepril, sold under the brand name Lotrel among others, is a fixed-dose combination medication used to treat high blood pressure. It is a combination of amlodipine, as the besilate, a calcium channel blocker, and benazepril, an angiotensin converting enzyme inhibitor. It may be used if a single agent is not sufficient. It is taken by mouth.

<span class="mw-page-title-main">Aliskiren</span> Medication

Aliskiren is the first in a class of drugs called direct renin inhibitors. It is used for essential (primary) hypertension. While used for high blood pressure, other better studied medications are typically recommended due to concerns of higher side effects and less evidence of benefit.

<span class="mw-page-title-main">Valsartan/hydrochlorothiazide</span> Chemical compound

Valsartan/hydrochlorothiazide, sold under the brand name Diovan HCT among others, is a medication used to treat high blood pressure when valsartan is not sufficient. It is a combination of valsartan, an angiotensin receptor blocker with hydrochlorothiazide, a diuretic. It is taken by mouth.

Losartan/hydrochlorothiazide, sold under the brand name Hyzaar among others, is a fixed-dose combination medication used to treat high blood pressure when losartan is not sufficient. It consists of losartan and hydrochlorothiazide. It is taken by mouth.

<span class="mw-page-title-main">Sacubitril/valsartan</span> Combination medication

Sacubitril/valsartan, sold under the brand name Entresto, is a fixed-dose combination medication for use in heart failure. It consists of the neprilysin inhibitor sacubitril and the angiotensin receptor blocker valsartan. The combination is sometimes described as an "angiotensin receptor-neprilysin inhibitor" (ARNi). In 2016, the American College of Cardiology/American Heart Association Task Force recommended it as a replacement for an ACE inhibitor or an angiotensin receptor blocker in people with heart failure with reduced ejection fraction.

Lisinopril/amlodipine, sold under the brand name Lisonorm among others, is a medication used to treat high blood pressure. It is a combination of lisinopril an ACE inhibitor with amlodipine a calcium channel blocker. It may be used when blood pressure is not well controlled with each of the two agents alone. It is taken by mouth.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 "Benazepril Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  2. ↑ "Benazepril Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  3. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN   9783527607495.
  4. ↑ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  5. ↑ "Benazepril - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  6. ↑ Dykewicz MS (April 2004). "Cough and Angioedema From Angiotensin-Converting Enzyme Inhibitors: New Insights Into Mechanisms and Management". Medscape. Retrieved 2 April 2014.
  7. ↑ "Lotensin package insert" (PDF). FDA. 2011. Retrieved 9 December 2020.
  8. ↑ 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". American Journal of Veterinary Research. 56 (12): 1620–1628. PMID   8599524.
  9. ↑ 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". Journal of Veterinary Internal Medicine. 23 (5): 977–983. doi: 10.1111/j.1939-1676.2009.0346.x . PMID   19572914.
  10. ↑ "Fortekor Flavor Tabs (5 mg) (Canada) for Animal Use". Drugs.com. Retrieved 9 December 2020.
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