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5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid

Acadesine

HCID 17513
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Grundinformationen

CAS
2627-69-2
Standard-SMILES
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N
Summenformel
C9H14N4O5
Durchschnittliche Molmasse
258,23 g/mol
Monoisotopische Masse
258,09641955

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Acadesine
IUPAC
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
Lokaler Name
5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid
Englischer Name
AICAR
Summenformel
C9H14N4O5
Molmasse
258.23

Namen und Synonyme

ACADESINE2627-69-2AICA-ribosideArasineAICA ribosideAcadesinaAIC-RibosideAcadesinumGP-1-110ProtaraDTXSID50460155-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,2
Polarare Oberfläche (TPSA)
157 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
3
Schwere Atome
18
Formalladung
0
Komplexität
330

Experimentelle und physikochemische Eigenschaften

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

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]

Physikochemische Eigenschaften

Schmelzpunkt
214 · 214-215 °C
Siedepunkt
726.3 · 726.3±60.0 °C(Predicted)
Dichte
2.06 · 2.06±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
2 O: · H2O: >10 mg/mL
Aggregatzustand
powder
pka
13.27 · 13.27±0.70(Predicted)
Farbe
tan
Biologische Quelle
rabbit
Wasserlöslichkeit
2 mg/ml · Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
Merck
14 · 14,16
Specific Activity
255 · 255-345nmol/min·mg
Stabilität
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
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
CAS Datenbank
2627 · 2627-69-2(CAS DataBase Reference)
EPA chemische Informationen
1 H-Imidazole-4-carboxamide, · 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingNegligible (approximately 1%)
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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

Verwendung und Herstellung

General Manufacturing Information1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenAICAR 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

MethyljodidAdenosin-3',5'-phosphatmonohydratNatriumhydroxidWasserstoffNatriumhydrogencarbonatNickelAmeisensureAmmoniak, wssrige Lsung

Nachgelagerte Produkte

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

Anbieter100 Anbieter

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Hebei Runbin Biotechnology Co. LTD13180553332 · [email protected]
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江苏创升生物工程有限公司13775204409 13775204409 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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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