9-β-D-Arabinofuranosyladenine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00559 |
| CAS | 5536-17-4 |
| Molecular Weight | 267.24 |
| Molecular Formula | C10H13N5O4 |
| Purity | ≥95% |
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Description
9-β-D-Arabinof uranosyladenine is a nucleoside antibiotic produced by Streptomyces antibioticusm and Str. herbaceusm. It has a strong weeding effect on a variety of monocotyledonous and dicotyledonous plants.
Specification
| Related CAS | 24356-66-9 (monohydrate) |
| Synonyms | Ara-adenosine; Vidarabine; 9-(b-D-Arabinofuranosyl)adenine; Adenine arabinoside; Arabinosyladenine; Spongoadenosine; Araadenosine; Arabinosyl adenine; (2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; 9-β-D-Arabinofuranosyl-9H-purin-6-amine; Adenine Arabinofuranoside |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| Canonical SMILES | C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N |
| InChI | InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1 |
| InChI Key | OIRDTQYFTABQOQ-UHTZMRCNSA-N |
Properties
| Appearance | White to Off-white Crystalline Powder |
| Antibiotic Activity Spectrum | viruses; neoplastics (Tumor) |
| Boiling Point | 676.3°C at 760 mmHg |
| Melting Point | 260-265°C (dec.) |
| Flash Point | 362.8±34.3 °C |
| Density | 2.08 g/cm3 |
| Solubility | Soluble in DMSO (Slightly, Heated), DMF (10 mg/mL), Ethanol (<1 mg/mL at 25°C), Water |
Reference Reading
1.An FDA Approved Anti-Viral Agent which Inhibits Adenylyl Cyclase Type 5 Protects the Ischemic Heart Even When Administered After Reperfusion.
Bravo C1, Vatner DE1, Pachon R1, Zhang J1, Vatner SF2. J Pharmacol Exp Ther. 2016 Mar 3. pii: jpet.116.232538. [Epub ahead of print]
An FDA approved anti-viral agent, known as Vidarabine or AraA, has features of inhibiting adenylyl cyclase type 5 (AC5) and protects against chronic coronary artery occlusion (CAO). The goal of this investigation was to determine if AraA protects against myocardial ischemia, even when delivered after coronary artery reperfusion (CAR). AraA, delivered after CAR in wild type mice, reduced infarct size by 55% compared to vehicle treated controls, whereas an equal dose of adenosine reduced infarct size only when administered before CAR. A 5 fold greater dose of adenosine was required to reduce infarct size, when delivered after CAR, which also reduced arterial pressure by 15%, whereas AraA did not affect pressure. The reduction in infarct size with AraA was prevented by a MEK/ERK blocker, a pathway also involved in the mechanism of protection of the AC5 knock out (KO) model. Infarct size was also reduced in cardiac specific AC5 KO mice similarly in the presence and absence of AraA, further suggesting that AraA protection involves the AC5 pathway.
2.Risk of secondary hypogammaglobulinaemia after Rituximab and Fludarabine in indolent non-Hodgkin lymphomas: A retrospective cohort study.
De Angelis F1, Tosti ME2, Capria S3, Russo E3, D'Elia GM3, Annechini G3, Stefanizzi C3, Foà R3, Pulsoni A3. Leuk Res. 2015 Dec;39(12):1382-8. doi: 10.1016/j.leukres.2015.10.013. Epub 2015 Nov 4.
The occurrence of secondary hypogammaglobulinemia (SH) after chemo-immunotherapy represents a potential side effect in patients with indolent non-Hodgkin lymphomas (iNHL). Few data are available on SH occurring after chemotherapy and/or Rituximab (R). We retrospectively investigated the incidence and the risk factors for SH and infectious complications in patients with iNHL after chemo-immunotherapy. Two hundred and sixty six patients treated between 1993 and 2011 were studied. Patients with a basal hypogammaglobulinemia or a monoclonal component were excluded. The incidence of SH was 2.2×1000 person-years (95% CI 1.6-2.9). Exposure to Fludarabine-based schedules (Fbs)±R was associated with a hazard ratio (HR) of 18.1 (95% CI: 4.3-77.0). Conversely, exposure to CHOP±R or CVP±R was not a risk factor (HR 0.3, 95% CI: 0.1-0.8; HR 0.3, 95% CI: 0.08-1.4, respectively). The role of R was studied comparing cohorts differing only for R; no differences were found comparing R-CHOP/R-CVP versus CHOP/CVP (HR 1.
3.Busulfan plus cyclophosphamide versus busulfan plus fludarabine as a preparative regimen for allogeneic haemopoietic stem-cell transplantation in patients with acute myeloid leukaemia: an open-label, multicentre, randomised, phase 3 trial.
Rambaldi A1, Grassi A2, Masciulli A3, Boschini C2, Micò MC2, Busca A4, Bruno B4, Cavattoni I5, Santarone S6, Raimondi R7, Montanari M8, Milone G9, Chiusolo P10, Pastore D11, Guidi S12, Patriarca F13, Risitano AM14, Saporiti G15, Pini M16, Terruzzi E17, Ar Lancet Oncol. 2015 Nov;16(15):1525-36. doi: 10.1016/S1470-2045(15)00200-4. Epub 2015 Sep 28.
BACKGROUND: The standard busulfan-cyclophosphamide myeloablative conditioning regimen is associated with substantial non-relapse mortality in patients older than 40 years with acute myeloid leukaemia who are undergoing allogeneic stem-cell transplantation. Because the combination of busulfan plus fludarabine has been proposed to reduce non-relapse mortality, we aimed to compare this treatment with busulfan plus cyclophosphamide as a preparative regimen in these patients.
4.Phase II Study of Allogeneic Transplantation for Older Patients With Acute Myeloid Leukemia in First Complete Remission Using a Reduced-Intensity Conditioning Regimen: Results From Cancer and Leukemia Group B 100103 (Alliance for Clinical Trials in Oncology)/Blood and Marrow Transplant Clinical Trial Network 0502.
Devine SM1, Owzar K2, Blum W2, Mulkey F2, Stone RM2, Hsu JW2, Champlin RE2, Chen YB2, Vij R2, Slack J2, Soiffer RJ2, Larson RA2, Shea TC2, Hars V2, Sibley AB2, Giralt S2, Carter S2, Horowitz MM2, Linker C2, Alyea EP2. J Clin Oncol. 2015 Dec 10;33(35):4167-75. doi: 10.1200/JCO.2015.62.7273. Epub 2015 Nov 2.
PURPOSE: Long-term survival rates for older patients with newly diagnosed acute myeloid leukemia (AML) are extremely low. Previous observational studies suggest that allogeneic hematopoietic stem-cell transplantation (HSCT) may improve overall survival (OS) because of lower rates of relapse. We sought to prospectively determine the value of HSCT for older patients with AML in first complete remission.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
