Available from stock

Adenine 9-ß-D-arabinofuranoside

SKU: A0279

Category: Antibiotics

Synonyms: Adenine Arabinoside , Arabinosyladenine , 9-&beta , -D-Arabinofuranosyladenine , Ara-A , Vidarabine , NSC 247519 , NSC 404241 , Vira-A; 5536-17-4
CAS-Number: C₁₀H₁₃N₅O₄
Molecular Formula: 267.24
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (HPLC)
Appearance: White to off-white poweder
Identity: 1H-NMR

Properties

Solvents: DMSO (20 mg/ml) or DMF (5 mg/ml). Slightly water (1 mg/ml).

Shipping: AMBIENT
Short Term Storage: -20°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H361
Precautionary statements: P281
GHS Symbol: GHS08
Signal word: Warning
Transportation: Not dangerous goods

Description: Adenine 9-β-D-arabinofuranoside is an analog of the nucleoside adenosine that has antiviral properties. It acts as a prodrug that, once phosphorylated by cellular enzymes, acts as both substrate and inhibitor of DNA polymerase. It has been shown to be effective against H. simplex, V. zoster and Epstein-Barr viruses. It is a potent inhibitor of AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2. It is also a neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes and showed anti-neoplastic activities. It has been shown to have inhibitory activity against SARS-CoV-2-ACE2 binding.
Smiles: NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
InChi Key: OIRDTQYFTABQOQ-UHTZMRCNSA-N
References: (1) S. Yoshida, et al., J. Biochem. 98, 433 (1985) , (2) W.B. Parker & Y. Cheng, Mol. Pharmacol. 31, 146 (1986) , (3) B. Bean, Clin. Microbiol. Rev. 5, 146 (1992) , (4) Y. Honma & N. Nitsu, Leuk. Lymphoma 399, 57 (2000) , (5) H. Kimura, et al., J. Pediatr. Hematol. Oncol. 23, 294 (2001) , (6) A. Kishimoto, et al., Mol. Biotechnol. 32, 17 (2006) , (7) M. Suzuki, et al., Antiviral Res. 72, 157 (2006) , (8) K.A. Jacobson & Z.-G. Gao, Nat. Rev. Drug Discov. 5, 247 (2006) (Review) , (9) S. Holzer, et al., ACS Chem. Biol. 14, 1904 (2019) , (10) M. Prajapat, et al., J. Mol. Graph. Model 101, 107716 (2020)
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

Adenine 9-β-D-arabinofuranoside is an analog of the nucleoside adenosine that has antiviral properties. It acts as a prodrug that, once phosphorylated by cellular enzymes, acts as both substrate and inhibitor of DNA polymerase. It has been shown to be effective against H. simplex, V. zoster and Epstein-Barr viruses. It is a potent inhibitor of AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2. It is also a neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes and showed anti-neoplastic activities. It has been shown to have inhibitory activity against SARS-CoV-2-ACE2 binding.

SKU: A0279 Category: Antibiotics

Additional information

Additional information

Synonyms	Adenine Arabinoside, Arabinosyladenine, 9-&beta, -D-Arabinofuranosyladenine, Ara-A, Vidarabine, NSC 247519, NSC 404241, Vira-A
Purity	≥99% (HPLC)
Appearance	White to off-white poweder
CAS-Number	5536-17-4
Molecular Formula	C10H13N5O4
Molecular Weight	267.24
Identity	1H-NMR
Solvents	DMSO (20 mg/ml) or DMF (5 mg/ml). Slightly water (1 mg/ml).
Smiles	NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
InChi Key	OIRDTQYFTABQOQ-UHTZMRCNSA-N
Shipping	AMBIENT
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H361
Precautionary statements	P281
GHS Symbol	GHS08
Signal word	Warning
Transportation	Not dangerous goods
References	(1) S. Yoshida, et al., J. Biochem. 98, 433 (1985), (2) W.B. Parker & Y. Cheng, Mol. Pharmacol. 31, 146 (1986), (3) B. Bean, Clin. Microbiol. Rev. 5, 146 (1992), (4) Y. Honma & N. Nitsu, Leuk. Lymphoma 399, 57 (2000), (5) H. Kimura, et al., J. Pediatr. Hematol. Oncol. 23, 294 (2001), (6) A. Kishimoto, et al., Mol. Biotechnol. 32, 17 (2006), (7) M. Suzuki, et al., Antiviral Res. 72, 157 (2006), (8) K.A. Jacobson & Z.-G. Gao, Nat. Rev. Drug Discov. 5, 247 (2006) (Review), (9) S. Holzer, et al., ACS Chem. Biol. 14, 1904 (2019), (10) M. Prajapat, et al., J. Mol. Graph. Model 101, 107716 (2020)
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
Quantity	5 g, 25 g, Bulk