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Acadesine

HCID 17513
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
2627-69-2
표준 SMILES
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N
분자식
C9H14N4O5
평균 분자량
258.23 g/mol
단동위원소 질량
258.09641955

개요

Acadesine is a 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects. It has a role as an antineoplastic agent and a platelet aggregation inhibitor. It is an aminoimidazole, a 1-ribosylimidazolecarboxamide and a nucleoside analogue.

이름 및 식별자

우선 이름
Acadesine
IUPAC
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
영어명
AICAR
분자식
C9H14N4O5
분자량
258.23

이름 및 동의어

ACADESINE2627-69-2AICA-ribosideArasineAICA ribosideAcadesinaAIC-RibosideAcadesinumGP-1-110ProtaraDTXSID50460155-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide
이름 더 보기
AAKGAMPKAMPK1AcairPRKAB1AMPKa1Acadesine, AICA
NSC-105823GP 1-1105-Amino-4-imidazolecarboxamide ribofuranoside5-Aminoimidazole-4-carboxamide ribonucleoside53IEF478465-Aminoimidazole-4-carboxamide riboside5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide5-Amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide

데이터베이스 식별자

CAS
2627-69-2
PubChem CID
17513
DTXSID
DTXSID5046015
ChEMBL
CHEMBL1551724
ChEBI
CHEBI:28498
UNII
53IEF47846
EC Number
220-097-5
Nikkaji
J14.878D

물성

구조 계산 물성

XLogP
-2.2
극성 표면적
157 Ų
수소 결합 공여자 수
5
수소 결합 수용자 수
7
회전 가능 결합 수
3
무거운 원자 수
18
형식 전하
0
복잡도
330

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section · 4건

170.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

153.55 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

153 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
214 · 214-215 °C
끓는 점
726.3 · 726.3±60.0 °C(Predicted)
밀도
2.06 · 2.06±0.1 g/cm3(Predicted)
저장 조건
-20 °C · -20°C
용해도
2 O: · H2O: >10 mg/mL
물리적 상태
가루
산도 계수 (pKa)
13.27 · 13.27±0.70(Predicted)
색상
갈색을 띤 노란색
생물학적 소스
rabbit
수용성
2 mg/ml의 · 2mg/ml의 DMSO에 용해됩니다. 1mg/ml 미만으로 물이나 에탄올에 용해됩니다.
Merck
14 · 14,16
Specific Activity
255 · 255-345nmol/min·mg
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 증류수에 용해된 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChI
1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N
SMILES
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
EPA
1 H-Imidazole-4-carboxamide, · 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)

화학적 성질

Solid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 4.4% (2 of 45) of reports.

Warning

H315 (93.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)

안전 데이터

wgk
3
tsca
TSCA listed
HS 번호
29349990
risk_code
36/37/38-61
hazard_code
Xi,T
safety_code
26-36-45-53
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 2건

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingNegligible (approximately 1%)
Pharmacodynamics · 1건

Acadesine has been shown to induce cell death apoptosis selectively in B-cells taken from healthy subjects and patients with B-CLL, with little effect on T-cells. As T-cells have an important role in fighting infection, it is anticipated that patients treated with acadesine will have a reduced risk of serious infections compared to those on current chemotherapies.

Mechanism of Action · 1건

The mechanism by which acadesine selectively kills B-cells is not yet fully elucidated. The action of acadesine does not require the tumour suppressor protein p53 like other treatments. This is important, as p53 is often missing or defective in cancerous B-cells. Studies have shown acadesine activates AMPK and induces apoptosis in B-cell chronic lymphocytic leukemia cells but not in T lymphocytes.

Biological Half-Life1 week

용도 및 제조

General Manufacturing Information1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-: ACTIVE
응용 분야 · 2건

용도AICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.

일반 설명Adenosine monophosphateprotein kinase (AMPK) activator 5-aminoimidazole-4-carboxamideribonucleotide(AICAR)modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses,cytokine production,cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.

상·하류 제품 정보

상류 원료

요오드 메탄3′,5′-사이클릭아데닐산수산화나트륨수소중탄산나트륨(중조)니켈개미산암모니아수

하류 제품

5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

공급사100 곳

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Hebei Henghe Import and Export Trading Co. LTD+8618032935937 18032916000 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海波以尔化工有限公司[email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
Cangzhou Wanyou New Material Technology Co.,Ltd18631714998 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
武汉泰易成生化药业有限公司027-88320699 · [email protected]
上海诺太医药科技有限公司021-50189163 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
武汉盈邦医药有限公司+86-13296627870; +86-13971566811 · [email protected]
HONG KONG IPURE BIOLOGY CO.,LIMITED86 18062405514 18062405514 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
Wuhan Demeikai Biotechnology Co., Ltd+8618942921723 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
CEG Chemical Science & Technology Co., Ltd.Mobile:13665161512
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
无锡亚肽生物科技有限公司0510-83583050 13771062561 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
AN PharmaTech Co Ltd86(21)68097365 · [email protected]
石家庄通洋进出口有限公司[email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
Hebei Runbin Biotechnology Co. LTD13180553332 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
武汉锶博睿医药技术有限公司027-87689766 13797071802 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18267553885 · [email protected]
江苏创升生物工程有限公司13775204409 13775204409 · [email protected]
추가 설명 · 1건

정의ChEBI: A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.

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