Ataluren

HCID 11219835

기본 정보

CAS
775304-57-9
표준 SMILES
O=C(O)c1cccc(-c2noc(-c3ccccc3F)n2)c1
InChIKey
OOUGLTULBSNHNF-UHFFFAOYSA-N
분자식
C15H9FN2O3
평균 분자량
284.24 g/mol
단동위원소 질량
284.05972037

개요

3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid is a ring assembly and an oxadiazole.

이름 및 식별자

우선 이름
Ataluren
IUPAC
3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
영어명
Ataluren
분자식
C15H9FN2O3
분자량
284.24

이름 및 동의어

Ataluren775304-57-9PTC124PTC-1243-[5-(2-Fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzoic acidTranslarnaK16AME9I3VAtalurenoDTXSID5046776Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-DTXCID3026776
이름 더 보기
CS-749AtalureAtarulonAtaluren, >=98%
Benzoic acid, 3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)-atalurenumRefChem:560297M09AX03922-364-8Ataluren (PTC124)Ataluren [USAN]PTC 124

데이터베이스 식별자

CAS
775304-57-9
PubChem CID
11219835
DTXSID
DTXSID5046776
ChEMBL
CHEMBL256997
ChEBI
CHEBI:94805
UNII
K16AME9I3V
EC Number
695-053-5、922-364-8
Nikkaji
J2.446.661B

물성

구조 계산 물성

XLogP
3.1
극성 표면적
76.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
6
회전 가능 결합 수
3
무거운 원자 수
21

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Musculo-skeletal system -> Other drugs for disorders of the musculo-skeletal system

Pharmaceuticals -> Listed in ZINC15

물리화학적 성질

녹는점
241 · 241 - 242°C
끓는 점
503.7 · 503.7±60.0 °C(Predicted)
밀도
1.379 · 1.379
저장 조건
Refrigerator
용해도
DMSO (약간 용해됨)
물리적 상태
흰색 내지 회백색 고체.

안전 및 규제

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

유해성 정보

Hazard Classes and CategoriesNot Classified

안전 데이터

wgk
WGK 3
HS 번호
2933998090
Hazard Classifications
STOT RE 2STOT SE 3
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 2건

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein BindingAtaluren is 99.6% bound to human plasma proteins and the binding is independent of plasma concentration. Ataluren does not distribute into red blood cells.
Mechanism of Action · 1건

Ataluren enables ribosomal readthrough of mRNA containing premature stop codons that otherwise would result in premature termination of protein chains. Use of ataluren allows cellular machinery to bypass nonsense mutations in genetic material, continue the translation process, and thereby restore the production of a full-length, functional protein. The research on the effects of Ataluren on the translation and stability of nonsense-containing mRNA in vitor show that Ataluren promoted readthrough at each of the nonsense codons, showing maximal activity with UGA, while having no effect on mRNA levels. Unlike the stable cell line assays, Ataluren did not discriminate significantly between the UAG and UAA mRNAs. Ataluren was a more potent nonsense-suppressing agent than gentamicin, and exhibited 4- to 15-fold stimulation of in vitro readthrough relative to the controls at levels similar to those in the stable cell reporter assays. These results indicate that Ataluren modulates termination efficiency at premature nonsense codons.

Biological Half-LifeAtaluren plasma half-life ranges from 2-6 hours and is unaffected either by dose or repeated administration.
Metabolism/Metabolites · 1건

Ataluren is metabolized by conjugation via uridine diphosphate glucuronosyltransferase (UGT) enzymes, predominantly UGT1A9 in liver and intestine. In vivo, the only metabolite detected in plasma after oral administration of radio-labelled ataluren was the ataluren-O-1β-acyl glucuronide; exposure to this metabolite in humans was approximately 8% of the plasma AUC of ataluren.

Absorption, Distribution and Excretion · 2건

Peak plasma levels of ataluren are attained approximately 1.5 hours after dosing in subjects who received medicinal product within 30 minutes of a meal.

After a single oral dose of radiolabeled ataluren, approximately half of the administered radioactive dose is recovered in the faeces and the remainder was recovered in the urine. In the urine, unchanged ataluren and the acyl glucuronide metabolite account for less than 1% and 49%, respectively, of the administered dose.

응용 분야 · 2건

개요Ataluren is a drug marketed under the trade name Translarna® which was developed by PTC Therapeutics and approved by the European Union in May 2014 for the treatment of Duchenne’s muscular dystrophy (DMD) and potentially other genetic disorders. Ataluren renders ribosomes less sensitive to premature stop or ‘read-through’ codons, which are thought to be beneficial in diseases such as DMD and cystic fibrosis.

용도Nonsense mutations create a premature termination of mRNA translation and have been implicated in various genetic disorders, including muscular dystrophy and cystic fibrosis. PTC-124 is a nonaminoglycoside that has been reported to selectively induce ribosomes to read through premature nonsense stop signals on mRNA, thus allowing the production of full-length, functional proteins. In a mouse model of cystic fibrosis caused by nonsense mutations, PTC-124 treatment (60 mg/kg s.c. injection or 0.3-0.9 mg/ml orally) has been shown to restore cystic fibrosis transmembrane conductance regulator (CFTR) protein expression and function. The target activity of PTC-124 was initially evaluated by firefly luciferase reporter cell-based nonsense codon assay (IC50 = 7 nM); however, subsequent assessments using a Renilla reniformis luciferase reporter have failed to produce nonsense codon suppression activity. Thus, while PTC-124 is in clinical testing in patients with nonsense mutations within the CFTR or dystrophin genes, controversy surrounds its exact mechanism of action.[Cayman Chemical]

공급사100 곳

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
上海波以尔化工有限公司[email protected]
芷威(上海)化学科技有限公司021-20221225 13917446399 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]

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