Levamlodipine
Grundinformationen
- CAS
103129-82-4- Standard-SMILES
CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)[C@@H]1c1ccccc1Cl- InChIKey
HTIQEAQVCYTUBX-KRWDZBQOSA-N- Summenformel
- C20H25ClN2O5
- Durchschnittliche Molmasse
- 408,9 g/mol
- Monoisotopische Masse
- 408,1451996
Überblick
(S)-amlodipine is the (4S)-enantiomer of amlodipine. It is an enantiomer of a (R)-amlodipine.
Namen und Bezeichner
- Bevorzugter Name
- Levamlodipine
- IUPAC
- 3-O-ethyl 5-O-methyl (4S)-2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
- Englischer Name
- (S)-Amlodipine
- Summenformel
- C20H25ClN2O5
- Molmasse
- 408.88
Namen und Synonyme
Levamlodipine103129-82-4S-AmlodipineAmlodipine, (s)-levamlodipino0P6NLP6806DTXSID509045043-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (4S)-3-Ethyl 5-methyl (4S)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate(-)-Amlodipine2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
Weitere Namen anzeigen
S-Amlodipine Base(4S)-Lodienl-AmlodipineLevoaMlodipine(S)-Amlodipine, >=99%Amlodipine (S)-IsomerLevoamlodipine Besylate
3,5-Pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (4S)-levamlodipinumRefChem:56702DTXCID201333652(S)-Amlodipine(4S)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl EsterLevamlodipine [INN]3-ethyl 5-methyl (S)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3
- Polarare Oberfläche (TPSA)
- 99,9 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 647
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Dissociation Constants8.6
Physikochemische Eigenschaften
- Schmelzpunkt
- 102 · 102-104°C
- Siedepunkt
- 527.2 · 527.2±50.0 °C(Predicted)
- Dichte
- 1.227 · 1.227
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- Löslichkeit
- Chloroform (Sparingly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 8.97 · 8.97±0.10(Predicted)
- Farbe
- White to Off-White
- Major Application
- pharmaceutical
- InChI
- InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1
- InChIKey
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1STOT RE 2
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingLevamlodipine is 93% protein bound in plasma, largely to human serum albumin.
Pharmacodynamics
Levamlodipine inhibits L-type calcium channels in vascular smooth muscle, reducing peripheral vascular resistance and blood pressure. It is given once daily in doses of 1.25-2.5mg in children and 2.5-5mg in adults. Patients should be counselled regarding the risk of symptomatic hypotension, worsening angina, and myocardial infarction.
Mechanism of Action
Levamlodipine blocks the transmembrane influx of calcium through L-type calcium channels into the vascular and cardiac smooth muscles resulting in vasodilation and a subsequent decrease in blood pressure. Levamlodipine inhibits calcium influx in vascular smooth muscle to a greater degree than in cardiac muscle, leading to decreased peripheral vascular resistance and lowered blood pressure. In vitro studies have shown a negative inotropic effect but this is unlikely to be clinically relevant.
Biological Half-LifeLevamlodipine has a half life of 30-50h.
Metabolism/Metabolites
Levamlodipine is 90% metabolized to inactive metabolites. Incubation with liver microsomes has shown that this metabolism is primarily mediated by CYP3A4. Levamlodipine's dehydrogenation to a pyridine metabolite (M9) is the most important metabolic pathway in human liver microsomes. This derivative can be further oxidatively deaminated or O-dealkylated, but does not appear to undergo O-demethylation like racemic amlodipine.
Absorption, Distribution and Excretion
Oral levamlodipine has a Tmax of 6-12h and a bioavailability of 64-90%. Absorption of levamlodipine is not significantly affected by food. 20mg or oral s-amlodipine besylate reaches a Cmax of 6.13±1.29ng/mL with a Tmax of 8.4±3.6h and an AUC of 351±72h\*ng/mL. 20mg or oral s-amlodipine maleate reaches a Cmax of 5.07±1.09ng/mL with a Tmax of 10.7±3.4h and an AUC of 330±88h\*ng/mL.
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…