Chemistry:Isradipine
-Isradipin_Structural_Formula_V1.svg) | |
| Clinical data | |
|---|---|
| Trade names | DynaCirc |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a693048 |
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| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Bioavailability | 15-24% |
| Protein binding | 95% |
| Metabolism | 100% Hepatic |
| Elimination half-life | 8 hours |
| Excretion | 70% Renal, 30% Fecal |
| Identifiers | |
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| CAS Number | |
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| DrugBank | |
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| ChEMBL | |
| Chemical and physical data | |
| Formula | C19H21N3O5 |
| Molar mass | 371.393 g·mol−1 |
| 3D model (JSmol) | |
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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.
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]
- Dizziness
- Warmth, redness, or tingly feeling under your skin
- Headache
- Weakness, tired feeling
- Nausea, vomiting, diarrhea, upset stomach
- Skin rash or itching
Serious side effects include: [3]
- Lightheadedness or fainting
- Shortness of breath, especially from minimal physical activity
- Swelling in the hands and feet
- Rapid and/or heavy heartbeat
- Chest pain
Drug interactions
It is advised that those using Isradipine not take Anzemet (Dolasetron), as both agents can cause a dose-dependent PR interval and QRS complex prolongation.[4]
Itraconazole exhibits a negative inotropic effect on the heart and thus could spur an additive effect when used concomitantly with Isradipine. Onmel/Sporanox 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 anti-biotic 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]
- Lethargy
- Sinus tachycardia
- Transient hypotension
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 ) - Form:[7]
| Enantiomers of Isradipine | |
|---|---|
-Isradipin_Structural_Formula_V1.svg) CAS-Nummer: 84260-63-9 |
-Isradipin_Structural_Formula_V1.svg) CAS-Nummer: 84260-64-0 |
References
- ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 465. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA465.
- ↑ 2.0 2.1 2.2 2.3 2.4 "Isradipine: Brands, Medical Use, Clinical Data". http://www.druglib.com/activeingredient/isradipine/.
- ↑ 3.0 3.1 "Isradipine Side Effects". https://www.drugs.com/sfx/isradipine-side-effects.html.
- ↑ "Isradipine and Anzemet Drug Interactions". https://www.drugs.com/drug-interactions/isradipine-with-onmel-1405-0-1406-15779.html.
- ↑ "Isradipine and Onmel Drug Interactions". https://www.drugs.com/drug-interactions/isradipine-with-onmel-1405-0-1406-15779.html.
- ↑ "Isradipine and Zanaflex Drug Interactions". https://www.drugs.com/drug-interactions/isradipine-with-zanaflex-1405-0-2205-1453.html.
- ↑ 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
- "Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts.". Eur J Med Res 11 (3): 93–6. 2006. PMID 16751108.
- "Comparison of blood pressure control with amlodipine and controlled-release isradipine: an open-label, drug substitution study.". The Journal of Clinical Hypertension 7 (4 Suppl 1): 27–31. 2005. doi:10.1111/j.1524-6175.2005.04450.x. PMID 15858400.
- "Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects.". Int J Neuropsychopharmacol 8 (2): 203–13. 2005. doi:10.1017/S1461145704005036. PMID 15850499.
- "An open trial comparing isradipine with hydralazine and methyl dopa in the treatment of patients with severe pre-eclampsia.". J Obstet Gynaecol 19 (3): 235–8. 1999. doi:10.1080/01443619964977. PMID 15512286.
- "'Rejuvenation' protects neurons in mouse models of Parkinson's disease.". Nature 447 (3): 1081–1086. 2007. doi:10.1038/nature05865. PMID 17558391.
External links
- Drug offers hope for Parkinson's - BBC News, 11 June 2007.
- [1] - Commentary of Chan et al. publication
- [2] - ArsTechnica - Why neurons die in Parkinson's patients
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