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9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-(CAS No. 5536-17-4)

9H-Purin-6-amine, 9-beta-D-arabinofuranosyl- C10H13N5O4 (cas 5536-17-4) Molecular Structure

5536-17-4 Structure

Identification and Related Records

【Name】
9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-
【CAS Registry number】
5536-17-4
【Synonyms】
Adenine,9-beta-D-arabinofuranosyl- (7CI,8CI)
6-Amino-9-beta-D-arabinofuranosylpurine
9-Arabinosyladenine
9-beta-D-Arabinoadenosine
9-beta-D-Arabinofuranosyl-9H-purin-6-amine
9-beta-D-Arabinofuranosyladenine
Adenine 9-beta-D-arabinofuranoside
Adeninearabinoside
Adenine beta-D-arabinofuranoside
Araadenosine
Arabinosyladenine
Arasena-A
CI-673
NSC 247519
NSC 404241
Spongoadenosine
Vira-A
beta-Ara-A
beta-D-Arabinofuranosyladenine
beta-D-Arabinosyladenine
【EINECS(EC#)】
226-893-9
【Molecular Formula】
C10H13N5O4 (Products with the same molecular formula)
【Molecular Weight】
267.28
【Inchi】
InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(16)1-19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
【Canonical SMILES】
C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)O
【MOL File】
5536-17-4.mol

Chemical and Physical Properties

【Appearance】
White to off-white crystalline powder.
【Density】
2.08g/cm3
【Melting Point】
260-265 °C (dec.)
【Boiling Point】
676.3°Cat760mmHg
【Refractive Index】
1.907
【Flash Point】
362.8°C
【Solubilities】
Soluble
【Color/Form】
Crystals from water
Needles from water
【Stability】
No data.
【HS Code】
29349990
【Storage temp】
−20°C
【Spectral properties】
Maximum absorption (pH 1): 257.5 nm (E = 12,7000); pH 7: 259 nm (E = 13,400); pH13: 259 nm (E = 14,000).
Specific optical rotation: -5 deg at 27 deg C/D (concentration by volume= 0.25 g in 100 ml water).
【Computed Properties】
Molecular Weight:267.24132 [g/mol]
Molecular Formula:C10H13N5O4
XLogP3:-1.1
H-Bond Donor:4
H-Bond Acceptor:4
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:267.096754
MonoIsotopic Mass:267.096754
Topological Polar Surface Area:140
Heavy Atom Count:19
Formal Charge:0
Complexity:335
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:4
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:4
Feature 3D Cation Count:4
Feature 3D Ring Count:3
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:135

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R63
【Safety Statements 】
36/37-36-26
【HazardClass】
6.1(a)
【Safety】
Poison by ingestion and intravenous routes. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by intravenous route: central nervous system, blood, and other effects. A skin and eye irritant. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
【PackingGroup 】
II
【Skin, Eye, and Respiratory Irritations】
Burning, itching, and mild irritation of the affected eye are the most common adverse effects of topical vidarabine therapy.
【Transport】
2811
【Formulations/Preparations】
Ophthalmic Ointment 3% (equivalent to vidarabine, Vira-A, Parke-Davis anhydrous 2.8%)
Parenteral: Concentrate, for injection, for iv infusion, 200 mg/ml (equivalent to 187.4 mg of anhydrous vidarabine per ml). Vira-A (with benzethonium chloride and phosphate buffers), Parke-Davis
/Vidarabine/ not currently approved for use in the United States
【Exposure Standards and Regulations】
Proposed regulation to exempt marketing applications for certain antibiotic drug products, including vidarabine, from regulatory provisions governing marketing exclusivity and patents. [Federal Register: January 24, 2000 (Volume 65, Number 15)]
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Vidarabine is included on this list.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Burning, itching, and mild irritation of the affected eye are the most common adverse effects of topical vidarabine therapy.
【Specification】

Crystalline
Safety Statements:36/37-36-26
36/37:Wear suitable protective clothing and gloves
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
【Octanol/Water Partition Coefficient】
log Kow = -1.11
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Originally prepared by chemical synthesis at Stanford Research Institute, and later isolated from a fermentation beer of Streptomyces antibioticus.
【Usage】
Medication.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
- Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
【Therapeutic Uses】
A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the VACCINIA VIRUS and varicella zoster virus
Vidarabine has been shown to possess antiviral activity against the following viruses in vitro: Herpes simplex types 1 and 2; vaccinia, varicella-zoster. Except for rhabdovirus and oncornavirus, vidarabine does not display in vitro antiviral activity against other RNA or DNA viruses, including adenovirus.
/EXPTL THER/ When adenovirus causes hemorrhagic cystitis in immunocompromised patients, vidarabine is used for its treatment because therapeutic choice is limited. Although vidarabine has been reported to be effective for these patients, its therapeutic basis has not yet been established. Vidarabine dose-dependently inhibited viral replication as assessed by a yield reduction assay. Viral protein synthesis was dose-dependently inhibited by vidarabine but not at all by acyclovir, and the degree of inhibition by vidarabine was different for each of the viral proteins, ranging from 0-40% of the untreated control. These results indicated the specificity and mechanism of action of vidarabine against adenovirus. The concentration of vidarabine and its metabolite in the bladder is suggested to exhibit effective anti-adenoviral activity in suppressing the replication of adenovirus. Thus, /the authors conclude that their/ results support vidarabine therapy as a possible candidate for adenovirus-induced hemorrhagic cystitis in immunocompromised patients. [Kurosaki K et al; Antivir Chem Chemother 15 (5): 281-5 (2004) .]
【Biomedical Effects and Toxicity】
Vira-A is rapidly deaminated to arabinosylhypoxanthine (Ara-Hx), the principal metabolite. ...Because of the low solubility of Vira-A, trace amounts of both Vira-A and Ara-Hx can be detected in the aqueous humor only if there is an epithelial defect in the cornea. If the cornea is normal, only trace amounts of Ara-Hx can be recovered from the aqueous humor. Systemic absorption of Vira-A should not be expected to occur following ocular administration and swallowing lacrimal secretions.
Vidarabine is poorly absorbed following oral, im, or SC administration. Following iv administration of vidarabine, 75-87% of the dose is rapidly deaminated by adenosine deaminase to ara-hypoxanthine. Ara-hypoxanthine also possesses antiviral activity but substantially less than that of vidarabine. Following slow iv administration of vidarabine 10 mg/kg in adults, peak plasma concentrations of the drug range from 0.2-0.4 ug/mL and peak plasma concentrations of ara-hypoxanthine range from 3-6 ug/mL. Plasma concentrations of vidarabine and ara-hypoxanthine are higher and more prolonged in patients with renal impairment.
Vidarabine and ara-hypoxanthine are widely distributed into body tissues and fluids and readily cross the blood-brain barrier. In patients with normal meninges, ara-hypoxanthine concentrations in the CSF are about 33-35% of concurrent plasma concentrations. Vidarabine crosses the placenta in animals. It is not known if vidarabine is distributed into milk. ... Vidarabine is 20-30% bound and ara-hypoxanthine is 0-3% bound to plasma proteins.
Vidarabine and ara-hypoxanthine are excreted mainly by the kidneys. Within 24 hours following iv administration of vidarabine 15 mg/kg in patients with normal renal function, 1-3% of the dose is excreted in urine as vidarabine and 41-53% of the dose is excreted as ara-hypoxanthine. There is no evidence of fecal excretion of the drug or metabolite.

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