Lesinurad
Grundinformationen
- CAS
1890222-25-9- Standard-SMILES
O=C(O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12- InChIKey
FGQFOYHRJSUHMR-UHFFFAOYSA-N- Summenformel
- C17H14BrN3O2S
- Durchschnittliche Molmasse
- 404,3 g/mol
- Monoisotopische Masse
- 402,99900979
Überblick
Lesinurad is a member of the class of triazoles that is [(3-bromo-1,2,4-triazol-5-yl)sulfanyl]acetic acid substituted at position 1 of the triazole ring by a 4-cyclopropylnaphthalen-1-yl group. Used for treatment of gout. It has a role as a uricosuric drug. It is a monocarboxylic acid, a member of naphthalenes, an aryl sulfide, a member of triazoles, an organobromine compound and a member of cyclopropanes.
Namen und Bezeichner
- Bevorzugter Name
- Lesinurad
- IUPAC
- 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid
- Englischer Name
- RDEA 594
- Summenformel
- C17H14BrN3O2S
- Molmasse
- 404.28
Namen und Synonyme
LESINURAD878672-00-5RDEA594ZurampicRDEA 594RDEA-59409ERP08I3W2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acidCHEBI:90929DUZALLO COMPONENT LESINURADDTXSID2010260912-{[5-broMo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid
Weitere Namen anzeigen
LesinurdResinadRescindRecinardReginaldResinardLesinurasLesurinad
{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acidlesinuradum((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetic acid2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl)sulfanyl)acetic acid2-((5-BROMO-4-(4-CYCLOPROPYLNAPHTHALEN-1-YL)-4H-1,2,4-TRIAZOL-3-YL)SULFANYL)ACETIC ACIDRefChem:56326M04AB05DTXCID901510348
Datenbank-Bezeichner
- CAS
1890222-25-9、1890222-26-0、878672-00-5- PubChem CID
- 53465279
- DTXSID
DTXSID201026091- ChEMBL
CHEMBL2105720- ChEBI
CHEBI:90929- UNII
- 09ERP08I3W、73WY698HZ7、Q59CAT99RS
- EC Number
- 689-245-8
- Nikkaji
- J3.671.265A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,7
- Polarare Oberfläche (TPSA)
- 93,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 479
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 171 oC · >171oC (dec.)
- Siedepunkt
- 643.7 · 643.7±65.0 °C(Predicted)
- Dichte
- 1.72 · 1.72±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated)
- pka
- 2.91 · 2.91±0.10(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- InChI
- InChI=1S/C17H14BrN3O2S/c18-16-19-20-17(24-9-15(22)23)21(16)14-8-7-11(10-5-6-10)12-3-1-2-4-13(12)14/h1-4,7-8,10H,5-6,9H2,(H,22,23)
- InChIKey
- FGQFOYHRJSUHMR-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CSC1N(C2=C3C(C=CC=C3)=C(C3CC3)C=C2)C(Br)=NN=1
Sicherheit und Regulatorisches
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)
Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Hepatotoxicity
In large clinical trials, serum enzyme elevations were rare during lesinurad therapy and no more common than with placebo, and no instances of clinically apparent liver injury attributable to lesinurad were reported. Clinical experience with lesinurad therapy has been limited, but there have yet to be reports of clinically apparent liver injury attributable to its use.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Protein BindingLesinurad is extensively bound to proteins in plasma (greater than 98%), mainly to albumin.
PharmacodynamicsDose-dependent reductions in serum uric acid levels and increases in urinary uric acid excretion have been observed following single and multiple oral doses of lesinurad.
Mechanism of Action
Lesinurad inhibits the activity of uric acid transporter 1 (URAT1) and organic anion transporter 4 (OAT4). URAT1 is a major transporter enzyme responsible for reuptake of uric acid from the renal tubules; inhibition of URAT1 function thereby increases excretion of uric acid.
Metabolism/MetabolitesLesinurad undergoes oxidative metabolism mainly via the polymorphic cytochrome P450 CYP2C9 enzyme.
FDA Pharmacological Classification
09ERP08I3W
LESINURAD
Established Pharmacologic Class [EPC] - Urate Transporter 1 Inhibitor
Mechanisms of Action [MoA] - Urate Transporter 1 Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 3A Inducers
Lesinurad is an Urate Transporter 1 Inhibitor. The mechanism of action of lesinurad is as an Urate Transporter 1 Inhibitor and Cytochrome P450 3A Inducer.
MeSH Pharmacological Classification
Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout.
Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma.
Absorption, Distribution and Excretion
Oral lesinurad is rapidly absorbed, reaching maximum plasma concentrations (Cmax) within 1–4 h following the administration a single 200 mg dose (in either the fed or fasted state).
Within 7 days following single dosing of radiolabeled lesinurad, 63% of administered radioactive dose was recovered in urine and 32% of administered radioactive dose was recovered in feces. Most of the radioactivity recovered in urine (> 60% of dose) occurred in the first 24 hours. Unchanged lesinurad in urine accounted for approximately 30% of the dose.
The mean steady state volume of distribution of lesinurad was approximately 20 L following intravenous dosing.
Anwendungen
BeschreibungApproved by the FDA late in 2015, lesinurad is an urate anion exchange transporter 1 (URAT1) inhibitor for use in the treatment of gout. Ardea Biosciences, which is a subsidiary of AstraZeneca, developed lesinurad to be used in a combination therapy with xanthine oxidase inhibitors for the treatment of hyperuricaemia associated with gout. The approval process is ongoing in several other countries across the globe, with the EMA Committee for Medicinal Products for Human Use giving lesinurad a positive opinion for use as an adjunctive therapy in combination with xanthine oxidase inhibitors to treat hyperuricaemia.
VerwendenLesinurad is used to synthesize febuxostat which is a non-purine analog inhibitor of xanthine oxidase. Febuxostat is approved by the European Medicines Agency and the US Food and Drug Administration for treating gout.
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Ergänzende Hinweise
DefinitionChEBI: A member of the class of triazoles that is [(3-bromo-1,2,4-triazol-5-yl)sulfanyl]acetic acid substituted at position 1 of the triazole ring by a 4-cyclopropylnaphthalen-1-yl group. Used for treatment of gout.
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