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Substance Name: Vidarabine [INN]
RN: 5536-17-4
UNII: 3XQD2MEW34
InChIKey: OIRDTQYFTABQOQ-UHTZMRCNSA-N

Note

  • 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.

Molecular Formula

  • C10-H13-N5-O4

Molecular Weight

  • 267.2437
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
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Names and Synonyms

Results Name

  • Vidarabine [INN]

Name of Substance

  • Vidarabine
  • Vidarabine anhydrous
  • Vidarabine [INN]

MeSH Heading

  • Vidarabine

Synonyms

  • 6-Amino-9-beta-D-arabinofuranosylpurine
  • 9-Arabinosyladenine
  • 9-beta-Arabinoadenosine
  • 9-beta-D-Arabinofuranosyladenine
  • 9beta-D-Arabinofuranosyladenine
  • 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-
  • 9H-Purin-6-amine, 9beta-D-arabinofuranosyl-
  • Adenine arabinoside
  • Adenine beta-D-arabinofuranoside
  • Adenine, 9-beta-D-arabinofuranosyl-
  • Adenine, 9beta-D-arabinofuranosyl-
  • Adenine-9-beta-D-arabinofuranoside
  • Adenine-beta-D-arabinofuranoside
  • AI3-52821
  • Ara-A
  • Araadenosine
  • Arabinoside adenine
  • Arabinosyl adenine
  • Arabinosyladenine
  • Arasena-A
  • beta-D-Arabinofuranosyladenine
  • beta-D-Arabinosyladenine
  • BRN 0624881
  • CCRIS 3383
  • EINECS 226-893-9
  • HSDB 6514
  • NSC 247519
  • NSC-404241
  • Spongoadenosine
  • UNII-3XQD2MEW34
  • Vidarabin
  • Vidarabina
  • Vidarabina [DCIT]
  • Vidarabine
  • Vidarabinum
  • Vidarabinum [INN-Latin]
  • Vira ATM
  • Vira-A

Systematic Names

  • 9-beta-D-Arabinofuranosyl-9H-purin-6-amine (9CI)
  • 9-beta-D-Arabinofuranosyladenine
  • 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-
  • Adenine, 9-beta-D-arabinofuranosyl-
  • Vidarabine

Registry Numbers

CAS Registry Number

  • 5536-17-4

FDA UNII

  • 3XQD2MEW34

System Generated Number

  • 0005536174

Structure Descriptors

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

InChIKey

OIRDTQYFTABQOQ-UHTZMRCNSA-N

Smiles

c1nc(c2c(n1)n(cn2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 300ug/kg (0.3mg/kg)   Journal of Infectious Diseases. Vol. 133, Pg. A192, 1976.
human TDLo intravenous 300ug/kg (0.3mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ANOREXIA (HUMAN
Journal of Infectious Diseases. Vol. 133, Pg. A192, 1976.
human TDLo intravenous 2mg/kg (2mg/kg) BEHAVIORAL: ATAXIA

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: TOXIC PSYCHOSIS
Journal of Infectious Diseases. Vol. 134, Pg. 75, 1976.
mouse LD50 intraperitoneal 3057mg/kg (3057mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
mouse LD50 intravenous 442mg/kg (442mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
mouse LD50 oral 7800ug/kg (7.8mg/kg)   "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 2, Pg. 962, 1978.
mouse LD50 subcutaneous 5086mg/kg (5086mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
rat LD50 intraperitoneal 1476mg/kg (1476mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
rat LD50 intravenous 302mg/kg (302mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
rat LD50 oral > 5gm/kg (5000mg/kg) LIVER: OTHER CHANGES Annals of the New York Academy of Sciences. Vol. 284, Pg. 6, 1977.
rat LD50 subcutaneous 8914mg/kg (8914mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 688, 1984.
women LDLo intravenous 105mg/kg/1W-I (105mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Canadian Medical Association Journal. Vol. 132, Pg. 392, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 257-257.5 deg C   EXP
log P (octanol-water) -1.11E+00 (none)   EXP
Water Solubility 8230 mg/L 25 EST
Vapor Pressure 7.00E-15 mm Hg 25 EST
Henry's Law Constant 1.11E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.38E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.