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75695-93-1 molecular structure
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3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

ChemBase ID: 155
Molecular Formular: C19H21N3O5
Molecular Mass: 371.38714
Monoisotopic Mass: 371.14812079
SMILES and InChIs

SMILES:
O(C(=O)C1=C(NC(=C(C1c1c2nonc2ccc1)C(=O)OC)C)C)C(C)C
Canonical SMILES:
COC(=O)C1=C(C)NC(=C(C1c1cccc2c1non2)C(=O)OC(C)C)C
InChI:
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
InChIKey:
HMJIYCCIJYRONP-UHFFFAOYSA-N

Cite this record

CBID:155 http://www.chembase.cn/molecule-155.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
IUPAC Traditional name
isradipine
Brand Name
Clivoten
DynaCire
DynaCire CR
DynaCirc
Dynacirc CR
Dynacrine
Esradin
Lomir
Prescal
Rebriden
Synonyms
(+/-)-Isradipine
Isradipino [Spanish]
Isradipinum [Latin]
Isrodipine
Isradipin
Isradipine
DynaCirc
Prescal
PN-200-110
4-(4-Benzofurazanyl)-1,-4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl 1-methylethyl ester
Isradipine
4-(4-Benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Methyl 1-Methylethyl Ester
Clivoten
Esr
DynaCirc
Esradin
Lomir
CAS Number
75695-93-1
MDL Number
MFCD00153820
PubChem SID
24724517
46505034
160963618
PubChem CID
3784

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.7748289  LogD (pH = 7.4) 1.995238 
Log P 1.9989158  Molar Refractivity 100.0842 cm3
Polarizability 38.38981 Å3 Polar Surface Area 103.55 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.0  LOG S -3.21 
Solubility (Water) 2.28e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: >10 mg/mL expand Show data source
Practically insoluble (< 10 mg/L at 37 °C) expand Show data source
Apperance
yellow solid expand Show data source
Yellow Solid expand Show data source
Melting Point
166-168°C expand Show data source
Hydrophobicity(logP)
2.901 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... CACNA2D1(781) expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Description
Store under nitrogen expand Show data source
Empirical Formula (Hill Notation)
C19H21N3O5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00270 external link
Item Information
Drug Groups approved
Description Isradipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. It is structurally related to felodipine, nifedipine, and nimodipine and is the most potent calcium-channel blocking agent of the DHP class. Isradipine binds to calcium channels with high affinity and specificity and inhibits calcium flux into cardiac and arterial smooth muscle cells. It exhibits greater selectivity towards arterial smooth muscle cells owing to alternative splicing of the alpha-1 subunit of the channel and increased prevalence of inactive channels in smooth muscle cells. Isradipine may be used to treat mild to moderate essential hypertension.
Indication For the management of mild to moderate essential hypertension. It may be used alone or concurrently with thiazide-type diuretics.
Pharmacology Isradipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium decreases the contractile activity of arterial smooth muscle cells and results in vasodilation. The vasodilatory effects of isradipine result in an overall decrease in blood pressure.
Toxicity Symptoms of overdose include lethargy, sinus tachycardia, and transient hypotension. Significant lethality was observed in mice given oral doses of over 200 mg/kg and rabbits given about 50 mg/kg of isradipine. Rats tolerated doses of over 2000 mg/kg without effects on survival.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Completely metabolized prior to excretion and no unchanged drug is detected in the urine.
Absorption Isradipine is 90%-95% absorbed and is subject to extensive first-pass metabolism, resulting in a bioavailability of about 15%-24%.
Half Life 8 hours
Protein Binding 95%
Elimination Approximately 60% to 65% of an administered dose is excreted in the urine and 25% to 30% in the feces.
References
Fletcher H, Roberts G, Mullings A, Forrester T: An open trial comparing isradipine with hydralazine and methyl dopa in the treatment of patients with severe pre-eclampsia. J Obstet Gynaecol. 1999 May;19(3):235-8. [Pubmed]
Ganz M, Mokabberi R, Sica DA: Comparison of blood pressure control with amlodipine and controlled-release isradipine: an open-label, drug substitution study. J Clin Hypertens (Greenwich). 2005 Apr;7(4 Suppl 1):27-31. [Pubmed]
Hattori T, Wang PL: Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts. Eur J Med Res. 2006 Mar 27;11(3):93-6. [Pubmed]
Johnson BA, Roache JD, Ait-Daoud N, Wallace C, Wells L, Dawes M, Wang Y: Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects. Int J Neuropsychopharmacol. 2005 Jun;8(2):203-13. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1662 external link
Research Area: Cardiovascular Disease
Biological Activity:
Isradipine(Dynacirc) is a calcium channel blocker with an IC50 of 34±8 μM.It is usually prescribed for the treatment of high blood pressure in order to reduce the risk of stroke and heart attack. [1] the interactive effects of isradipine and blockers or enhancers of nonselective cation channels (NSCCs) and Na+/Ca2+ exchangers (NCXs). Normal human gingival fibroblast Gin-1 cells were used. The [Ca2+]i was measured with the Ca2+-sensitive fluorescent dye fura-2/AM. Changes in the fluorescence intensity of fura-2 in the cells were recorded with a video-imaging analysis system. Ca2+ antagonists (nifedipine, verapamil, and diltiazem in the concentration range of 1 to 20 μM) other than isradipine also raised the [Ca2+]i. [2] 
Sigma Aldrich - I6658 external link
Biochem/physiol Actions
L-type calcium channel blocker (also referred to as dihydropyridine-type calcium channel blocker); antihypertensive.
Toronto Research Chemicals - I925000 external link
Dihydropyridine calcium channel blocker. Antihypertensive; antianginal.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hattori T et al. Eur J Med Res. 2006 Mar 27;11(3)
  • • Nelson, E.B., et al.: Clin. Pharmacol. Ther., 40, 694 (1986)
  • • Hof, R.P., et al.: J. Cardiovasc. Pharmacol., 8, 221 (1986)
  • • Fletcher H, Roberts G, Mullings A, Forrester T: An open trial comparing isradipine with hydralazine and methyl dopa in the treatment of patients with severe pre-eclampsia. J Obstet Gynaecol. 1999 May;19(3):235-8. Pubmed
  • • Ganz M, Mokabberi R, Sica DA: Comparison of blood pressure control with amlodipine and controlled-release isradipine: an open-label, drug substitution study. J Clin Hypertens (Greenwich). 2005 Apr;7(4 Suppl 1):27-31. Pubmed
  • • Hattori T, Wang PL: Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts. Eur J Med Res. 2006 Mar 27;11(3):93-6. Pubmed
  • • Johnson BA, Roache JD, Ait-Daoud N, Wallace C, Wells L, Dawes M, Wang Y: Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects. Int J Neuropsychopharmacol. 2005 Jun;8(2):203-13. Pubmed
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PATENTS

PATENTS

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