Vidarabine

Base Information

• Chemical Name: Vidarabine
• CAS No.: 5536-17-4
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 29349990
• European Community (EC) Number: 226-893-9
• NSC Number: 757383
• UNII: 3XQD2MEW34
• DSSTox Substance ID: DTXSID80873976
• Nikkaji Number: J3.415K
• Wikipedia: Vidarabine
• Wikidata: Q415107
• NCI Thesaurus Code: C77393
• RXCUI: 2108659
• Pharos Ligand ID: QVBN8BKVXM2B
• Metabolomics Workbench ID: 42602
• ChEMBL ID: CHEMBL1090
• Mol file: 5536-17-4.mol

Synonyms:9 beta Arabinofuranosyladenine;9 beta D Arabinofuranosyladenine;9-beta-Arabinofuranosyladenine;9-beta-D-Arabinofuranosyladenine;Adenine Arabinoside;alpha Ara A;alpha D Arabinofuranosyladenine;alpha-Ara A;alpha-D-Arabinofuranosyladenine;Ara A;Ara-A;Arabinofuranosyladenine;Arabinoside, Adenine;Arabinosyladenine;beta Ara A;beta-Ara A;Vidarabine;Vira A;Vira-A;ViraA

Chemical Property of Vidarabine

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 3.14E-17mmHg at 25°C
• Melting Point: 260-265 °C (dec.)
• Refractive Index: 1.907
• Boiling Point: 676.3 °C at 760 mmHg
• PKA: pKa 3.55(H2O t=20 I=0.1 (KCl)) (Uncertain);11.4 (Uncertain)
• Flash Point: 362.8 °C
• PSA: 139.54000
• Density: 2.08 g/cm³
• LogP: -1.39880
• Storage Temp.: ?20°C
• Solubility.: DMSO (Slightly, Heated)
• Water Solubility.: Soluble in DMF (10 mg/ml), 0.5 M HCl (50 mg/ml), DMSO (53 mg/ml at 25°C), ethanol (<1 mg/ml at 25°C), and water (3 mg/ml at 25°C).
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

99% ^*data from raw suppliers

Vidarabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn:Harmful
• Statements: R63:
• Safety Statements: S36/37:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
• Recent ClinicalTrials: Comparison of Foscarnet Versus Vidarabine in the Treatment of Herpes Infection in Patients With AIDS Who Have Not Had Success With Acyclovir
• Description: Vidarabine (adenine arabinoside) is the stereoisomer of adenosine. This analog of a purine nucleoside exhibits selective activity against the herpes virus. The ribose residue is replaced with an arabinose residue. Like acyclovir, it turns into mono-, di-, and triphosphate in cells infected by a virus, thus inhibiting DNA polymerase, and correspondingly preventing DNA synthesis of the virus approximately 20–40 times more than in “host” cells. It is easily metabolized to a less active, yet nonetheless antiviral compound—arabinosylhypoxanthine. It has been successfully used for herpetic encephalitis, and for complicated shingles. It is used in the form of eye drops for herpetic keratoconjuctivitis. A synonym of this drug is Vira-A. Vidarabine 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. Vidarabine is particularly effective against H. simplex and V. zoster viruses.
• Uses: antifungal;Antiviral;Adenosine antimetabolite. active component of chili peppers, analgesic and therapeutic agent for arthritis, potential prophylactic for type 1 diabetes Vidarabine, is an antiviral drug which is active against herpes simplex and varicella zoster viruses.
• Indications: Vidarabine (adenine arabinoside, Vira-A) is an adenine nucleoside analogue containing arabinose in place of ribose. It is obtained from cultures of Streptomyces antibioticus and has activity against HSV-1, HSV-2, VZV, CMV, HBV, poxviruses, hepadnaviruses, rhabdoviruses, and certain RNA tumor viruses.
• Therapeutic Function: Antiviral
• Clinical Use: The principal use of vidarabine is in the treatment of HSV keratoconjunctivitis. It is also used to treat superficial keratitis in patients unresponsive or hypersensitive to topical idoxuridine.

Technology Process of Vidarabine

There total 48 articles about Vidarabine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

9-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)adenine (3257-73-6) → arabinosyl adenine (5536-17-4)

Guidance literature:

With cyclohexene; palladium dihydroxide; In ethanol; for 2h; Heating;

DOI:10.1055/s-1981-29467

Reference yield: 94.0%

8-carboxamido-2'-O-tosyladenosine (76994-88-2) → arabinosyl adenine (5536-17-4)

Guidance literature:

In pyridine; water; for 12h; Heating;

DOI:10.1039/c39800001191

Reference yield: 93.0%

araU (3083-77-0) + adenosine (58-61-7) → arabinosyl adenine (5536-17-4)

Guidance literature:

With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase; In aq. phosphate buffer; at 52 ℃; for 16h; pH=7; Enzymatic reaction;

DOI:10.1134/S1068162016040105

upstream raw materials:

9-(2',3',5'-tri-O-benzyl-β-D-arabinofuranosyl)adenine

9-(2-O-acetyl-β-D-arabinofuranosyl)adenine

9-<3-O-acetyl-β-D-arabinofuranosyl>adenine

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

Downstream raw materials:

(2R,3S,4S,5R)-2-(6-Amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-ol

(2R,3R,4S,5R)-5-(6-Amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-ol

N6-benzoyl-9-β-D-arabinofuranosyladenine

araU

Refernces

• 1、 Luenzmann,Schramm. "-". . p. 263. Retrieved 1968.
• 2、 -. "Production process of arabinoside". Paragraph 0026; 0031-0032; 0033; 0038-0039; 0040; 0045-0046. . Retrieved 2020/12/31.