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Wikipedia

Isradipine

January 01, 1970

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.

Isradipine
Clinical data
Trade namesDynaCirc
AHFS/Drugs.comMonograph
MedlinePlusa693048
Pregnancy
category
  • C
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability15-24%
Protein binding95%
Metabolism100% Hepatic
Elimination half-life8 hours
Excretion70% 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
  • 75695-93-1 Y
PubChem CID
  • 3784
DrugBank
  • DB00270 Y
ChemSpider
  • 3652 Y
UNII
  • YO1UK1S598
KEGG
  • D00349 Y
ChEMBL
  • ChEMBL1648 Y
CompTox Dashboard (EPA)
  • DTXSID4023179
ECHA InfoCard100.158.721
Chemical and physical data
FormulaC19H21N3O5
Molar mass371.393 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Y
  • Key:HMJIYCCIJYRONP-UHFFFAOYSA-N Y
  (verify)

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

Medical uses edit

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

Side effects edit

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 edit

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 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 edit

Symptoms of an Isradipine overdose include:[2]

Stereochemistry edit

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
 
CAS-Nummer: 84260-63-9 		 
CAS-Nummer: 84260-64-0

References edit

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 465. ISBN 9783527607495.
  2. ^ a b c d e "Isradipine: Brands, Medical Use, Clinical Data".
  3. ^ a b "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 edit

  • Hattori T, Wang P (2006). "Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts". Eur J Med Res. 11 (3): 93–6. PMID 16751108.
  • Ganz M, Mokabberi R, Sica D (2005). "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. doi:10.1111/j.1524-6175.2005.04450.x. PMC 8109349. PMID 15858400.
  • Johnson B, Roache J, Ait-Daoud N, Wallace C, Wells L, Dawes M, Wang Y (2005). "Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects". Int J Neuropsychopharmacol. 8 (2): 203–13. doi:10.1017/S1461145704005036. PMID 15850499.
  • Fletcher H, Roberts G, Mullings A, Forrester T (1999). "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. doi:10.1080/01443619964977. PMID 15512286.
  • Chan CS, Guzman JN, Ilijic E, Mercer JN, Rick C, Tkatch T, Meredith GE, Surmeier DJ (2007). "'Rejuvenation' protects neurons in mouse models of Parkinson's disease". Nature. 447 (3): 1081–1086. doi:10.1038/nature05865. PMID 17558391. S2CID 4429534.

External links edit

  • MedlinePlus DrugInfo medmaster-a693048
  • Diseases Database (DDB): 30003
  • 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

January 01, 1970
isradipine, tradenames, dynacirc, prescal, calcium, channel, blocker, dihydropyridine, class, usually, prescribed, treatment, high, blood, pressure, order, reduce, risk, stroke, heart, attack, clinical, datatrade, namesdynacircahfs, drugs, commonographmedlinep. 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 IsradipineClinical dataTrade namesDynaCircAHFS Drugs comMonographMedlinePlusa693048PregnancycategoryCRoutes ofadministrationOralATC codeC08CA03 WHO Legal statusLegal statusUK POM Prescription only US onlyPharmacokinetic dataBioavailability15 24 Protein binding95 Metabolism100 HepaticElimination half life8 hoursExcretion70 Renal 30 FecalIdentifiersIUPAC name 3 methyl 5 propan 2 yl 4 2 1 3 benzoxadiazol 4 yl 2 6 dimethyl 1 4 dihydropyridine 3 5 dicarboxylateCAS Number75695 93 1 YPubChem CID3784DrugBankDB00270 YChemSpider3652 YUNIIYO1UK1S598KEGGD00349 YChEMBLChEMBL1648 YCompTox Dashboard EPA DTXSID4023179ECHA InfoCard100 158 721Chemical and physical dataFormulaC 19H 21N 3O 5Molar mass371 393 g mol 13D model JSmol Interactive imageSMILES O C OC C3 C N C C C O OC C C C3c1cccc2nonc12 C CInChI 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 YKey HMJIYCCIJYRONP UHFFFAOYSA N Y verify It was patented in 1978 and approved for medical use in 1989 1 Contents 1 Medical uses 2 Side effects 3 Drug interactions 4 Overdose 5 Stereochemistry 6 References 7 Further reading 8 External linksMedical uses editIsradipine is given as either a 2 5 mg or 5 mg capsule 2 Side effects editCommon 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 painDrug interactions editIt 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 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 editSymptoms of an Isradipine overdose include 2 Lethargy Sinus tachycardia Transient hypotensionStereochemistry editIsradipine 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 nbsp CAS Nummer 84260 63 9 nbsp CAS Nummer 84260 64 0References edit Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 465 ISBN 9783527607495 a b c d e Isradipine Brands Medical Use Clinical Data a b Isradipine Side Effects Isradipine and Anzemet Drug Interactions Isradipine and Onmel Drug Interactions Isradipine and Zanaflex Drug Interactions Rote Liste Service GmbH Hrsg Rote Liste 2017 Arzneimittelverzeichnis fur 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 editHattori T Wang P 2006 Calcium antagonist isradipine induced calcium influx through nonselective cation channels in human gingival fibroblasts Eur J Med Res 11 3 93 6 PMID 16751108 Ganz M Mokabberi R Sica D 2005 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 doi 10 1111 j 1524 6175 2005 04450 x PMC 8109349 PMID 15858400 Johnson B Roache J Ait Daoud N Wallace C Wells L Dawes M Wang Y 2005 Effects of isradipine a dihydropyridine class calcium channel antagonist on d methamphetamine s subjective and reinforcing effects Int J Neuropsychopharmacol 8 2 203 13 doi 10 1017 S1461145704005036 PMID 15850499 Fletcher H Roberts G Mullings A Forrester T 1999 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 doi 10 1080 01443619964977 PMID 15512286 Chan CS Guzman JN Ilijic E Mercer JN Rick C Tkatch T Meredith GE Surmeier DJ 2007 Rejuvenation protects neurons in mouse models of Parkinson s disease Nature 447 3 1081 1086 doi 10 1038 nature05865 PMID 17558391 S2CID 4429534 External links editMedlinePlus DrugInfo medmaster a693048 Diseases Database DDB 30003 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 Retrieved from https en wikipedia org w index php title Isradipine amp oldid 1219866605, wikipedia, wiki, book, books, library,

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