Vidarabine

Names

[ Name ]:
Vidarabine

[Synonym ]:
Adenine, 9-β-D-arabinofuranosyl-
Vidarabine
adenine arabinoside
ara-adenosine
MFCD00065471
9-(β-D-Arabinofuranosyl)-9H-purin-6-amine
9H-Purin-6-amine, 9-β-D-arabinofuranosyl-
9-(b-D-Arabinofuranosyl)adenine
9-β-D-arabinofuranosyl-9H-purin-6-amine
ara-A
6-Amino-9-b-D-arabinofuranosylpurine
EINECS 226-893-9
Adenine-β-D-arabinofuranoside
9-β-Arabinoadenosine
9-(β-D-arabinofuranosyl)-9H-adenine
9H-Purin-6-amine, 9.β.-D-arabinofuranosyl-
9-(β-D-glycero-Pentofuranosyl)-9H-purin-6-amine
9H-purin-6-amine, 9-β-D-glycero-pentofuranosyl-
Adenine, 9β-D-arabinofuranosyl-
6-Amino-9-β-D-arabinofuranosylpurine
araA
Vidarabine Monohydrate
9-β-D-Arabinofuranosyladenine

Biological Activity

[Description]:

Vidarabine is an antiviral drug which is active against herpes simplex and varicella zoster viruses.Target: DNA/RNA SynthesisVidarabine is 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 [1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Infection

[References]

[1]. Whitley, R., et al., Vidarabine: a preliminary review of its pharmacological properties and therapeutic use. Drugs, 1980. 20(4): p. 267-82.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Boiling Point ]:
676.3±65.0 °C at 760 mmHg

[ Melting Point ]:
260-265ºC (dec.)

[ Molecular Formula ]:
C₁₀H₁₃N₅O₄

[ Molecular Weight ]:
267.241

[ Flash Point ]:
362.8±34.3 °C

[ Exact Mass ]:
267.096741

[ PSA ]:
139.54000

[ LogP ]:
-1.02

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.907

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU6200000

CHEMICAL NAME :: Adenine, 9-beta-D-arabinofuranosyl-

CAS REGISTRY NUMBER :: 5536-17-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 48

MOLECULAR FORMULA :: C10-H13-N5-O4

MOLECULAR WEIGHT :: 267.28

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IZ D- ET5OTJ B1Q CQ DQ *D-ARABINO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 105 mg/kg/1W-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - tremor

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 300 ug/kg

TOXIC EFFECTS :: Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Brain and Coverings - changes in surface EEG Behavioral - toxic psychosis Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1476 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8914 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 302 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3057 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5086 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 442 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4200 mg/kg/28D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 61600 mg/kg/4W-I

TOXIC EFFECTS :: Behavioral - muscle weakness Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1400 mg/kg/28D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 2100 mg/kg/28D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - visual field changes Behavioral - tremor Behavioral - muscle weakness

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 2 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 2 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 2500 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - body wall

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 2500 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 1316 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 2613 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 2613 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - respiratory system Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 260 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 13 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Mammal - species unspecified Cells - not otherwise specified

DOSE/DURATION :: 1 mmol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 120,139,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5559 No. of Facilities: 26 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1307 (estimated) No. of Female Employees: 664 (estimated)

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R63

[ Safety Phrases ]:
36/37-36-26

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
AU6200000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29349990

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