Grundinformationen
- Standard-SMILES
COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc2nonc12- InChIKey
HMJIYCCIJYRONP-UHFFFAOYSA-N- Summenformel
- C19H21N3O5
- Durchschnittliche Molmasse
- 371,4 g/mol
- Monoisotopische Masse
- 371,14812078
Namen und Bezeichner
- Bevorzugter Name
- Isradipine
- IUPAC
- 3-O-methyl 5-O-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
- Englischer Name
- Isradipine
- Summenformel
- C19H21N3O5
- Molmasse
- 371.39
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
75695-93-1- PubChem CID
- 3784
- DTXSID
DTXSID4023179- ChEMBL
CHEMBL1648、CHEMBL315436、CHEMBL3211306- ChEBI
CHEBI:6073- UNII
- YO1UK1S598
- EC Number
- 630-420-5
- Nikkaji
- J33.142B、J356.392H、J356.393F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,3
- Polarare Oberfläche (TPSA)
- 104 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 27
- Formalladung
- 0
- Komplexität
- 685
Experimentelle und physikochemische Eigenschaften
LogP
4.28
2.901
Solubility
Practically insoluble (< 10 mg/L at 37 °C)
2.28e-01 g/L
Melting Point
168-170 °C
168 - 170 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 166 · 166-1680C
- Siedepunkt
- 501.9 · 501.9±60.0 °C(Predicted)
- Dichte
- 1.249 · 1.249±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 26 mg/mL · DMSO: ~26 mg/mL
- Aggregatzustand
- solid
- pka
- 2.56 · 2.56±0.70(Predicted)
- Farbe
- yellow
- Merck
- 14 · 14,5240
- BCS Class
- 2 · 2/4
- Stabilität
- 2 years · Stable for 2 years from date of purchsae as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
- Major Application
- pharmaceutical (small molecule)
- 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
- SMILES
- C1(C)NC(C)=C(C(OC(C)C)=O)C(C2C3C(C=CC=2)=NON=3)C=1C(OC)=O
- CAS Datenbank
- 75695 · 75695-93-1(CAS DataBase Reference)
- NIST chemische Informationen
- Isradipine(75695-93-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301 (98%): Toxic if swallowed [Danger Acute toxicity, oral];H319 (92.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H372 (92.2%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure];H400 (98%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (98%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P260, P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P319, P321, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Isradipine
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Because no information is available on the use of isradipine during breastfeeding, an alternate drug may be preferred.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2934990002
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system;C08 - Calcium channel blockers;C08C - Selective calcium channel blockers with mainly vascular effects;C08CA - Dihydropyridine derivatives;C08CA03 - Isradipine
QC - Cardiovascular system;QC08 - Calcium channel blockers;QC08C - Selective calcium channel blockers with mainly vascular effects;QC08CA - Dihydropyridine derivatives;QC08CA03 - Isradipine
Pharmacodynamics
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.
Mechanism of Action
Isradipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. There are at least five different types of calcium channels in <i>Homo sapiens</i>: L-, N-, P/Q-, R- and T-type. CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction. Similar to other DHP CCBs, isradipine binds directly to inactive calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives isradipine additional arterial selectivity. At therapeutic sub-toxic concentrations, isradipine has little effect on cardiac myocytes and conduction cells.
FDA Pharmacological Classification
YO1UK1S598
ISRADIPINE
Mechanisms of Action [MoA] - Calcium Channel Antagonists
Established Pharmacologic Class [EPC] - Dihydropyridine Calcium Channel Blocker
Chemical Structure [CS] - Dihydropyridines
Isradipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of isradipine is as a Calcium Channel Antagonist.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion
Isradipine is 90%-95% absorbed and is subject to extensive first-pass metabolism, resulting in a bioavailability of about 15%-24%.
Approximately 60% to 65% of an administered dose is excreted in the urine and 25% to 30% in the feces.
Verwendung und Herstellung
Anwendungen
BeschreibungIsradipine is a long-acting calcium blocker effective in the treatment of essential hypertension. The advantages of isradipine as compared with other dihydropyridine calcium antagonists include a "gentle" onset and fewer contraindications. It can be taken by patients with diabetes mellitus, chronic obstructive airway diseases, gout, congestive heart failure or ischemic heart disease.
VerwendenIsradipine is a L-type calcium channel blocker, Isradipine has anti-atherosclerotic effects in animals and improves endothelium-mediated nitric oxide (NO)-dependent vasodilation in vitro. Additional studies indicate that Isradipine may provide a neuroprotective effect in a rat model of focal ischemia and that Isradipine produces a dose-dependent sparing of dopamine neuronal fibers and cell bodies.
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