5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid
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- 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
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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
- Aggregatzustand
- powder
- pka
- 13.27±0.70(Predicted)
- Farbe
- tan
- 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
- 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.
- InChIKey
- RTRQQBHATOEIAF-UUOKFMHZSA-N
- 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)
| Bildanzeige (GHS) |
 
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| Alarmwort |
Achtung |
| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H315 |
Verursacht Hautreizungen. |
Hautreizung |
Kategorie 2 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P302+P352, P321,P332+P313, P362 |
| H319 |
Verursacht schwere Augenreizung. |
Schwere Augenreizung |
Kategorie 2 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P305+P351+P338,P337+P313P |
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| 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. |
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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 monophosphate?protein kinase (AMPK) activator 5-aminoimidazole-4-carboxamide?ribonucleotide?(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.
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( 336)Lieferanten
2627-69-2(5-Amino-1-β-D-ribofuranosyl-1H-imidazol-4-carboxamid)Verwandte Suche:
Inosin
Guanosin, zyklisches 3',5'-(Hydrogen-phosphat), Mononatriumsalz
Xanthosin
Inosin-2',3',5'-triacetat
3'-Guanylsure, Dinatriumsalz
4-Aminoimidazol-5-carboxamid
2',3'-Isopropylideninosin
5'-Xanthylsure, Dinatriumsalz
Inosin 5'-monophosphatdinatriumsalzhydrat
Guanosin, N-(1-Oxobutyl)-, zyklisches 3',5'-(Hydrogen-phosphat)-2'-butanoat, Mononatriumsalz
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-carboxamid
5-Amino-1-(3,5-O-phosphinico-β-D-ribofuranosyl)-1H-imidazol-4-carboxamid
Inosin-cyclisch-3',5'-(hydrogenphosphat)
- 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
- AICAR
- AICA-RIBOSIDE
- 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
- 5-AMino-4-iMidazole
carboxaMide Riboside
- Arasine
- GP 1-110
- NSC 105823
- 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
- ANTI-AMPK ALPHA 1(C-TERMINAL) antibody produced in rabbit
- 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
- 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
- Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide, 5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside
- Anti-PRKAB1 (Protein kinase, AMP-activated, beta 1 non-catalytic subunit)
- Hydroxymethylglutaryl-CoA reductase kinase
- 5′-AMP-activated protein kinase catalytic subunit alpha-2
- AMPK2
- ANTI-AMPK ALPHA2(C-TERMINAL) antibody produced in rabbit
- PRKAA2
- 5′-AMP-activated protein kinase subunit β-1
- AMPK subunit β-1
- AMPKb
- AMPK (α2/β2/γ1), active, His tagged human
- MGC61468
- MGC8666
- PRKAA
- PRKAB2
- PRKAG1
- Anti-AMPK β1 antibody produced in rabbit
- AMPKa1
