Isradipine

Last updated
Isradipine
Isradipine.svg
Clinical data
Trade names DynaCirc
AHFS/Drugs.com Monograph
MedlinePlus a693048
Pregnancy
category
  • C
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 15-24%
Protein binding 95%
Metabolism 100% Hepatic
Elimination half-life 8 hours
Excretion 70% Renal, 30% Fecal
Identifiers
  • 3-Methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.158.721 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H21N3O5
Molar mass 371.393 g·mol−1
3D model (JSmol)
  • O=C(OC)\C3=C(\N\C(=C(\C(=O)OC(C)C)C3c1cccc2nonc12)C)C
  • InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3 Yes check.svgY
  • Key:HMJIYCCIJYRONP-UHFFFAOYSA-N Yes check.svgY
   (verify)

Isradipine (tradenames DynaCirc, Prescal) is a calcium channel blocker of the dihydropyridine class. It is usually prescribed for the treatment of high blood pressure in order to reduce the risk of stroke and heart attack.

Contents

It was patented in 1978 and approved for medical use in 1989. [1]

Medical uses

Isradipine is given as either a 2.5 mg or 5 mg capsule. [2]

Side effects

Common side effects include: [3]

Serious side effects include: [3]

Drug interactions

It is advised that those using isradipine not take dolasetron (Anzemet), as both agents can cause a dose-dependent PR interval and QRS complex prolongation. [4]

Itraconazole (Onmel/Sporanox) exhibits a negative inotropic effect on the heart and thus could spur an additive effect when used concomitantly with isradipine. Itraconazole also inhibits an important cytochrome liver enzyme (CYP 450 3A4) which is needed to metabolize isradipine and other calcium channel blockers. This will increase plasma levels of isradipine and could cause an unintentional overdose of the medication. Caution is advised when administering both agents together. [5]

Tizanidine demonstrates anti-hypertensive effects and should be avoided in patients taking isradipine due to the possibility of synergism between both medications. [6]

The antibiotic rifampin lowered plasma concentrations of isradipine to below detectable limits. [2]

Cimetidine increased isradipine mean peak plasma levels. A downward dose adjustment may be necessary with this particular instance of polypharmacy. [2]

Severe hypotension was reported with fentanyl anesthesia when it was combined with other calcium channel blockers. Even though isradipine, another calcium channel blocker, has not been used in conjunction with fentanyl anesthesia in any studies, caution is advised. [2]

Overdose

Symptoms of an isradipine overdose include: [2]

Stereochemistry

Isradipine contains a stereocenter and consists of two enantiomers, more precisely atropisomers. This is a racemate, i.e. a 1: 1 mixture of (R)- and the (S)-forms: [7]

Enantiomers of Isradipine
(R)-Isradipin Structural Formula V1.svg
CAS-Nummer: 84260-63-9
(S)-Isradipin Structural Formula V1.svg
CAS-Nummer: 84260-64-0

Related Research Articles

<span class="mw-page-title-main">Fentanyl</span> Opioid medication

Fentanyl is a highly potent synthetic piperidine opioid primarily used as an analgesic. It is 20 to 40 times more potent than heroin and 100 times more potent than morphine; its primary clinical utility is in pain management for cancer patients and those recovering from painful surgeries. Fentanyl is also used as a sedative. Depending on the method of delivery, fentanyl can be very fast acting and ingesting a relatively small quantity can cause overdose. Fentanyl works by activating μ-opioid receptors. Fentanyl is sold under the brand names Actiq, Duragesic and Sublimaze, among others.

Calcium channel blockers (CCB), calcium channel antagonists or calcium antagonists are a group of medications that disrupt the movement of calcium through calcium channels. Calcium channel blockers are used as antihypertensive drugs, i.e., as medications to decrease blood pressure in patients with hypertension. CCBs are particularly effective against large vessel stiffness, one of the common causes of elevated systolic blood pressure in elderly patients. Calcium channel blockers are also frequently used to alter heart rate, to prevent peripheral and cerebral vasospasm, and to reduce chest pain caused by angina pectoris.

<span class="mw-page-title-main">Verapamil</span> Calcium channel blocker medication

Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina, and supraventricular tachycardia. It may also be used for the prevention of migraines and cluster headaches. It is given by mouth or by injection into a vein.

<span class="mw-page-title-main">Amlodipine</span> Medication against high blood pressure

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">Atenolol</span> Beta blocker medication

Atenolol is a beta blocker medication primarily used to treat high blood pressure and heart-associated chest pain. Although used to treat high blood pressure, it does not seem to improve mortality in those with the condition. Other uses include the prevention of migraines and treatment of certain irregular heart beats. It is taken orally or by intravenous injection. It can also be used with other blood pressure medications.

<span class="mw-page-title-main">Nifedipine</span> Calcium channel blocker medication

Nifedipine, sold under the brand name Procardia among others, is a calcium channel blocker medication used to manage angina, high blood pressure, Raynaud's phenomenon, and premature labor. It is one of the treatments of choice for Prinzmetal angina. It may be used to treat severe high blood pressure in pregnancy. Its use in preterm labor may allow more time for steroids to improve the baby's lung function and provide time for transfer of the mother to a well qualified medical facility before delivery. It is a calcium channel blocker of the dihydropyridine type. Nifedipine is taken by mouth and comes in fast- and slow-release formulations.

<span class="mw-page-title-main">Diltiazem</span> Calcium channel blocker medication

Diltiazem, sold under the brand name Cardizem among others, is a nondihydropyridine calcium channel blocker medication used to treat high blood pressure, angina, and certain heart arrhythmias. It may also be used in hyperthyroidism if beta blockers cannot be used. It is taken by mouth or injection into a vein. When given by injection, effects typically begin within a few minutes and last a few hours.

<span class="mw-page-title-main">Metoprolol</span> Medication of the selective β1 receptor blocker type

Metoprolol, sold under the brand name Lopressor among others, is a medication used to treat angina and a number of conditions involving an abnormally fast heart rate. It is also used to prevent further heart problems after myocardial infarction and to prevent headaches in those with migraines. It is a selectiveβ1 receptor blocker medication. It is taken by mouth or is given intravenously.

<span class="mw-page-title-main">Nimodipine</span> Antihypertensive drug of the calcium channel blocker class

Nimodipine, sold under the brand name Nimotop among others, is a calcium channel blocker used in preventing vasospasm secondary to subarachnoid hemorrhage. It was originally developed within the calcium channel blocker class as it was used for the treatment of high blood pressure, but is not used for this indication.

In anaesthesia and advanced airway management, rapid sequence induction (RSI) – also referred to as rapid sequence intubation or as rapid sequence induction and intubation (RSII) or as crash induction – is a special process for endotracheal intubation that is used where the patient is at a high risk of pulmonary aspiration. It differs from other techniques for inducing general anesthesia in that several extra precautions are taken to minimize the time between giving the induction drugs and securing the tube, during which period the patient's airway is essentially unprotected.

<span class="mw-page-title-main">Xylazine</span> Veterinary anesthetic, sedative and analgesic

Xylazine is a structural analog of clonidine and an α2-adrenergic receptor agonist, sold under many trade names worldwide, most notably the Bayer brand name Rompun, as well as Anased, Sedazine and Chanazine.

<span class="mw-page-title-main">Ethosuximide</span> Medication used to treat absence seizures

Ethosuximide, sold under the brand name Zarontin among others, is a medication used to treat absence seizures. It may be used by itself or with other antiseizure medications such as valproic acid. Ethosuximide is taken by mouth.

<span class="mw-page-title-main">Cinnarizine</span> Antihistamine and calcium channel blocker medication

Cinnarizine is an antihistamine and calcium channel blocker of the diphenylmethylpiperazine group. It is prescribed for nausea and vomiting due to motion sickness or other sources such as chemotherapy, vertigo, or Ménière's disease. Cinnarizine is one of the leading causes of drug-induced parkinsonism.

<span class="mw-page-title-main">Analeptic</span> Drug class

An analeptic, in medicine, is a central nervous system stimulant. The term "analeptic" typically refers to respiratory stimulants. Analeptics are central nervous system (CNS) stimulants that include a wide variety of medications used to treat depression, attention deficit hyperactivity disorder (ADHD), and respiratory depression. Analeptics can also be used as convulsants, with low doses causing patients to experience heightened awareness, restlessness, and rapid breathing. The primary medical use of these drugs is as an anesthetic recovery tool or to treat emergency respiratory depression. Other drugs of this category are prethcamide, pentylenetetrazole, and nikethamide. Nikethamide is now withdrawn due to risk of convulsions. Analeptics have recently been used to better understand the treatment of a barbiturate overdose. Through the use of agents, researchers were able to treat obtundation and respiratory depression.

<span class="mw-page-title-main">Lercanidipine</span> Antihypertensive drug of the calcium channel blocker class

Lercanidipine is an antihypertensive drug. It belongs to the dihydropyridine class of calcium channel blockers, which work by relaxing and opening the blood vessels allowing the blood to circulate more freely around the body. This lowers the blood pressure and allows the heart to work more efficiently.

<span class="mw-page-title-main">Flunarizine</span> Calcium channel blocker medication

Flunarizine, sold under the brand name Sibelium among others, is a drug classified as a calcium antagonist which is used for various indications. It is not available by prescription in the United States or Japan. The drug was discovered at Janssen Pharmaceutica (R14950) in 1968.

<span class="mw-page-title-main">Nitrendipine</span> Antihypertensive drug of the calcium channel blocker class

Nitrendipine is a dihydropyridine calcium channel blocker. It is used in the treatment of primary (essential) hypertension to decrease blood pressure and can reduce the cardiotoxicity of cocaine.

Ca<sub>v</sub>1.3 Protein found in humans

Calcium channel, voltage-dependent, L type, alpha 1D subunit is a protein that in humans is encoded by the CACNA1D gene. Cav1.3 channels belong to the Cav1 family, which form L-type calcium currents and are sensitive to selective inhibition by dihydropyridines (DHP).

<span class="mw-page-title-main">Clevidipine</span> Antihypertensive drug of the calcium channel blocker class

Clevidipine is a dihydropyridine calcium channel blocker indicated for the reduction of blood pressure when oral therapy is not feasible or not desirable. Clevidipine is used IV only and practitioners titrate this drug to lower blood pressure. It has a half-life of approximately one minute. It is rapidly inactivated by esterases.

<span class="mw-page-title-main">Efonidipine</span> Antihypertensive drug of the calcium channel blocker class

Efonidipine (INN) is a dihydropyridine calcium channel blocker marketed by Shionogi & Co. of Japan. It was launched in 1995, under the brand name Landel (ランデル). The drug blocks both T-type and L-type calcium channels. Drug Controller General of India (DCGI) has approved the use of efonidipine in India. It is launched under the brand name "Efnocar".

References

  1. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 465. ISBN   9783527607495.
  2. 1 2 3 4 5 "Isradipine: Brands, Medical Use, Clinical Data". Archived from the original on 2019-09-13. Retrieved 2013-01-21.
  3. 1 2 "Isradipine Side Effects".
  4. "Isradipine and Anzemet Drug Interactions".
  5. "Isradipine and Onmel Drug Interactions".
  6. "Isradipine and Zanaflex Drug Interactions".
  7. Rote Liste Service GmbH (Hrsg.): Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57, ISBN   978-3-946057-10-9, S. 193.

Further reading