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

AICAR Struktur
2627-69-2
CAS-Nr.
2627-69-2
Bezeichnung:
5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid
Englisch Name:
AICAR
Synonyma:
AAKG;AMPK;ACADESINE;AMPK1;PRKAB1;Acadesine, AICA;5-Aminoimidazole-4-carboxamide riboside;5-Aminoimidazole-4-carboxamide ribonucleoside;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-B-D-RIBOFURANOSIDE;{[(2S,3R,4R,5R)-5-(5-aMino-4-carbaMoyl-1H-iMidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]Methoxy}phosphonic acid
CBNumber:
CB1675294
Summenformel:
C9H14N4O5
Molgewicht:
258.23
MOL-Datei:
2627-69-2.mol

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

Schmelzpunkt:
214-215 °C
Siedepunkt:
726.3±60.0 °C(Predicted)
Dichte
2.06±0.1 g/cm3(Predicted)
storage temp. 
-20°C
Löslichkeit
H2O: >10 mg/mL
pka
13.27±0.70(Predicted)
Aggregatzustand
powder
Farbe
tan
Biologische Quelle
rabbit
Wasserlöslichkeit
Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
maximale Wellenlänge (λmax)
265nm(NaOH)(lit.)
Merck 
14,16
Specific Activity
255-345nmol/min·mg
Stabilität:
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
2627-69-2(CAS DataBase Reference)
EPA chemische Informationen
1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xi,T
R-Sätze: 36/37/38-61
S-Sätze: 26-36-45-53
WGK Germany  3
TSCA  TSCA listed
HS Code  29349990
Speicherklasse 11 - Combustible Solids
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
Sicherheit
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

Solid

Verwenden

AICAR 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.

Definition

ChEBI: 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.

Allgemeine Beschreibung

Adenosine 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.

Biologische Aktivität

Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes.

Nebenwirkungen

AICAR is an AMPK (adenosine 5′-monophosphate (AMP)-activated protein kinase) activator that has been shown to have significant endurance-enhancing effects and is banned for use as a doping agent by the World Anti-Doping Agency. Overactivation of AMPK, or activation in the wrong tissues, can lead to serious side effects, including neurodegeneration or preventing cell division. Accumulation of naturally occurring AICAR in the body has also been linked to metabolic disorders in humans. However, AICAR has not been approved for human treatment and cannot be used as a drug. Therefore, its safety has yet to be verified.

Clinical claims and research

AICAR has proved in vivo anti-tumor effects in xenograft models. It is currently under clinical trial phase I/II to treat patients with chronic lymphocytic leukemia and has shown good safety and tolerability properties, although some side effects have been reported.

5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 403)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Anko Intermational Trade Limited
+86-18073326374 +8618073326374;
sales@goodpeptides.com China 59 58
Shanghai Yimeixin Technology Co., LTD

China 210 58
Hebei Lutong Import and Export Co., Ltd
+8618131159658
judy@hbjbrh.com China 72 58
LIDE PHARMACEUTICALS LIMITED
+86-2558409506 +86-18913920737
louis@lidepharma.com China 300 58
Hainan Fubai Trading Co., LTD
+undefined852-57423927
13313004729@163.com China 103 58
.GZ HONESTCHEM CO.,LTD
+8615013270415
honestchemical@foxmail.com China 298 58
Wuhan Han Sheng New Material Technology Co.,Ltd
+8617798174412
admin01@hsnm.com.cn China 2097 58
Hebei Xinsheng New Material Technology Co., LTD.
+86-16632316109
xinshengkeji@xsmaterial.com China 1085 58
Anhui Ruihan Technology Co., Ltd
+8617756083858
daisy@anhuiruihan.com China 973 58
Shijiazhuang Saixin Technology Co., Ltd.
+86-16632312509 +86-16632315022
saixinkeji@aliyun.com China 86 58

2627-69-2(5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid)Verwandte Suche:


  • 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside,98%
  • 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosideAICAR
  • 5-Aminomidazole-4-carboxamide-1-β-D-ribofuranoside
  • ACADESINE
  • AICAR
  • AICA-RIBOSIDE
  • AMPK
  • 1-Deoxy-1-[(4-carbamoyl-5-amino-1H-imidazole)-1-yl]-β-D-ribofuranose
  • 1-β-D-Ribofuranosyl-5-amino-1H-imidazole-4-carboxamide
  • 5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
  • AICA-β-D-Riboside
  • {[(2S,3R,4R,5R)-5-(5-aMino-4-carbaMoyl-1H-iMidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]Methoxy}phosphonic acid
  • 5-AMino-4-iMidazole carboxaMide Riboside
  • Arasine
  • GP 1-110
  • NSC 105823
  • Acadesine, AICA
  • AICAR, Free Base
  • 5-aMino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-iMidazole-4-carboxaMide
  • N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide
  • AICAR,5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide
  • 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranose ,98%
  • Acadesine(Aicar,NSC 105823)
  • 5-Amino-4-carbamoyl-1-(beta-D-ribofuranosyl)-1H-imidazole, AICAR
  • Acadesine/AICAR
  • AICA, Acadesine, AICA-ribaoside
  • 1H-IMidazole-4-carboxaMide,5-aMino-1-b-D-ribofuranosyl-
  • 5′-AMP-activated protein kinase catalytic subunit alpha-1
  • AMPK1
  • ANTI-AMPK ALPHA 1(C-TERMINAL) antibody produced in rabbit
  • AICAR Alternate
  • 5-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
  • SR9011 white powder 99%
  • ICAR
  • AMPK alpha 2 
  • SR9011 white powder
  • AICAR - Acadesine | NSC 105823 | AICA-riboside | Arasine
  • CS-1981
  • Acair
  • High quality AICAR CAS: 2627-69-2 Acadesine factory sales
  • AICA-Riboside - CAS 2627-69-2 - Calbiochem
  • Z-RIBOSIDE
  • 5-amino-1-beta-d-ribofuranosyl-1h-imidazole-4-carboxamid
  • N1-(BETA-D-RIBOFURANOSYL)-5-AMINOIMIDAZOLE-4-CARBOXAMIDE
  • 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide
  • 5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide
  • 5-Amino-4-imidazolecarboxamide ribofuranoside
  • 5-Aminoimidazole-4-carboxamide ribonucleoside
  • 5-Aminoimidazole-4-carboxamide riboside
  • AIC-Riboside
  • Aminoimidazole-4-carboxamide-1-D-Ribofuranoside
  • 5-AMINOIMIDAZOLE-4-BETA-D-RIBOFURANOSE
  • AMINOIMIDAZOLE-4-CARBOXAMIDE-1-SS-D-RIBOFURANOSIDE
  • AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSIDE
  • AICAR, Acadesine
  • 5-Aminoimidazole-4-carboxamide-1-b-D-ribofuranose
  • 5-Aminoimidazole-4-carboxamide-1-β-riboside
  • 5-amino-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamide
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