Solifenacin

HCID 154059

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Grundinformationen

CAS
242478-37-1
Standard-SMILES
O=C(O[C@H]1CN2CCC1CC2)N1CCc2ccccc2[C@@H]1c1ccccc1
InChIKey
FBOUYBDGKBSUES-VXKWHMMOSA-N
Summenformel
C23H26N2O2
Durchschnittliche Molmasse
362,5 g/mol
Monoisotopische Masse
362,19942807

Überblick

Solifenacin is a member of isoquinolines.

Namen und Bezeichner

Bevorzugter Name
Solifenacin
IUPAC
[(3R)-1-azabicyclo[2.2.2]octan-3-yl] (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

Namen und Synonyme

Solifenacin242478-37-1solifenacineSolifenacinaA8910SQJ1U[(3R)-1-azabicyclo[2.2.2]octan-3-yl] (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylateNSC-759144DTXSID3048289(3R)-1-azabicyclo[2.2.2]octan-3-yl (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate((8r)-1-azabicyclo(2.2.2)octan-8-yl) (1s)-1-phenyl-3,4-dihydro-1h-isoQUINOLINE-2-carboxylate2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-,1-azabicyclo(2.2.2)oct-3-yl ester, (R-(R*,S*))-solifenacinum
Weitere Namen anzeigen
((3R)-1-azabicyclo(2.2.2)octan-3-yl) (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate(3R)-1-azabicyclo(2.2.2)octan-3-yl (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate[(8R)-1-azabicyclo[2.2.2]octan-8-yl] (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylateRefChem:56468DTXCID8028264G04BD08Soliten(+)-Solifenacin

Datenbank-Bezeichner

CAS
242478-37-1
PubChem CID
154059
DTXSID
DTXSID3048289
ChEMBL
CHEMBL1734
ChEBI
CHEBI:135530
UNII
A8910SQJ1U
Nikkaji
J1.594.869H

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
4
Polarare Oberfläche (TPSA)
32,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
27

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Muscarinic Antagonists; Parasympatholytics
Melting Point134-136
Collision Cross Section181.84 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Sicherheit und Regulatorisches

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Like most anticholinergic agents, solifenacin has not been linked to liver enzyme elevations during therapy or to instances of clinically apparent liver injury with jaundice. In multiple prospective clinical trials of solifenacin in patients with overactive bladder syndrome, ALT elevations were reported in less than 1% of treated subjects, rates similar to that of placebo-recipients. Despite widespread clinical use for almost two decades, there has been only a single published case report of possible liver injury due to darifenacin use. An elderly woman with end stage liver injury developed transient elevations of serum aminotransferases and alkaline phosphatase without jaundice two weeks after starting solifenacin. Thus, liver injury due to solifenacin must be rare if it occurs at all.

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

solifenacin

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

G04BD08

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingSolifenacin is 93-96% protein bound in plasma, mainly to alpha-1-acid glycoprotein.
Pharmacodynamics · 1 Eintrag

Solifenacin antagonizes the M2 and M3 muscarinic receptors in the bladder to treat an overactive bladder. It has a long duration of action as it is usually taken once daily. Patients taking solifenacin should be aware of the risks of angioedema and anaphylaxis.

Mechanism of Action · 1 Eintrag

Solifenacin is a competitive muscarinic receptor antagonist. It has the highest affinity for M3, M1, and M2 muscarinic receptors. 80% of the muscarinic receptors in the bladder are M2, while 20% are M3. Solifenacin's antagonism of the M3 receptor prevents contraction of the detrusor muscle, while antagonism of the M2 receptor may prevent contraction of smooth muscle in the bladder.

Biological Half-LifeThe elimination half life of solifenacin ranges from 33-85 hours.
Metabolism/Metabolites · 1 Eintrag

Solifenacin undergoes N-oxidation at the quinuclidin ring by cytochrome P450, though the exact enzymes are not revealed in the literature. The tetrahydroisoquinolone ring is 4R-hydroxylated by CYP3A4, CYP1A1, and CYP2D6. A 4R-hydroxy N-oxide metabolite is also formed by CYP3A4. Finally, solifenacin can undergo direct glucuronidation. Only solifenacin and the 4R-hydroxy metabolite are pharmacologically active.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100

Anbieter100 Anbieter

上海策嵘生物科技有限公司[email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海炎泽化工有限公司15345144255 19975051755 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

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