CAS 1890222-25-9 Lesinurad (HCID 53465279)

基本情報

CAS: 1890222-25-9
標準SMILES: O=C(O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12
InChIKey: FGQFOYHRJSUHMR-UHFFFAOYSA-N
分子式: C17H14BrN3O2S
平均分子量: 404.3 g/mol
単同位体質量: 402.99900979

概要

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.

名称と識別子

優先名称: Lesinurad
IUPAC: 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid
現地名: Lesinurad
英語名: RDEA 594
分子式: C17H14BrN3O2S
分子量: 404.28

名称と別名

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

名称をさらに表示

レシヌラド2-{[5-ブロモ-4-(4-シクロプロピルナフタレン-1-イル)-4H-1,2,4-トリアゾール-3-イル]スルファニル}酢酸(4-(4-シクロプロピル-1-ナフチル)-5-ブロモ-4H-1,2,4-トリアゾール-3-イルチオ)酢酸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

物性

構造計算による物性

XLogP: 4.7
極性表面積: 93.3 Å²
水素結合供与体数: 1
水素結合受容体数: 5
回転可能結合数: 5
重原子数: 24
形式電荷: 0
複雑度: 479

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

物理化学的性質

融点: 171 oC · >171oC (dec.)
沸点: 643.7 · 643.7±65.0 °C(Predicted)
比重(密度): 1.72 · 1.72±0.1 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C Freezer, Under inert atmosphere
溶解性: DMSO（微量）、メタノール（微量、加温）
酸解離定数(Pka): 2.91 · 2.91±0.10(Predicted)
外見: 個体
色: ホワイトからオフホワイト
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

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Hepatotoxicity · 1 件

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.

安全データ

wgk: WGK 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

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 · 1 件

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 · 6 件

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.