idoxuridine

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Names

[ CAS No. ]:
54-42-2

[ Name ]:
idoxuridine

[Synonym ]:
5-Iodo-2'-desoxyuridine
UNII-LGP81V5245
Dendrid (Trade name)
5-Iodo-2'-Deoxyuridine
Idoxene
Idulea
1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione
idoxuridine
STOXIL
Ophthalmadine
HERPLEX
Uracil, 5-iodo-1-(2-deoxy-β-D-ribofuranosyl)-
EINECS 200-207-8
1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-iodpyrimidin-2,4(1H,3H)-dion
Kerecid
2′-Deoxy-5-iodouridine
2'-Deoxy-5-iodouridine
Virudox
Uridine, 2'-deoxy-5-iodo-
5-Iodo-2′-deoxyuridine
MFCD00134656
Iduridin

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Melting Point ]:
194 °C(lit.)

[ Molecular Formula ]:
C₉H₁₁IN₂O₅

[ Molecular Weight ]:
354.099

[ Exact Mass ]:
353.971252

[ PSA ]:
104.55000

[ LogP ]:
-0.52

[ Index of Refraction ]:
1.715

[ Water Solubility ]:
1.6 g/L (20 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YU7700000

CHEMICAL NAME :: Uridine, 2'-deoxy-5-iodo-

CAS REGISTRY NUMBER :: 54-42-2

BEILSTEIN REFERENCE NO. :: 0030397

LAST UPDATED :: 199806

DATA ITEMS CITED :: 37

MOLECULAR FORMULA :: C9-H11-I-N2-O5

MOLECULAR WEIGHT :: 354.12

WISWESSER LINE NOTATION :: T6NVMVJ EI A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4 gm/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 :: >10 gm/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 :: 1 gm/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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4589 mg/kg/18D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg/8W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 7 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 :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: female 16-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Ocular

DOSE :: 1350 mg/kg

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

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Ocular

DOSE :: 3250 ug/kg

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

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sperm Morphology

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - rabbit Kidney

DOSE/DURATION :: 1 mg/L

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,390,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5053 No. of Facilities: 21 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 618 (estimated) No. of Female Employees: 318 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335-H341-H361

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R45;R46;R61

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YU7700000

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

2'-deoxyuridine
5-Iodouracil
((2R,3S,5R)-3-Acetoxy-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
5-chloromercurio-2-'-deoxyuridine
1,3,4,6-Tetrachloro-3a,6a-diphenylglycouril
Thymidine
3,5'-Di-O-acetyl-2'-deoxyuridine
5-(TriMethylstannyl)-2'-deoxyuridine

DownStream

2'-deoxyuridine
5-Chloro-2'-deoxyuridine
1-[(2R,4S,5R)-5-(hydroxymethyl)-4-phenylselanyloxolan-2-yl]-5-iodopyrimidine-2,4-dione
Aids186752
2-Ethynylpyrimidine
((2R,3S,5R)-3-Acetoxy-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
5-dodec-1-ynyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
2-Deoxy-β-D-ribofuranose
5-Iodouracil
Uracil

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Developing structure-activity relationships for the prediction of hepatotoxicity.

Chem. Res. Toxicol. 23 , 1215-22, (2010)

Drug-induced liver injury is a major issue of concern and has led to the withdrawal of a significant number of marketed drugs. An understanding of structure-activity relationships (SARs) of chemicals ...

A predictive ligand-based Bayesian model for human drug-induced liver injury.

Drug Metab. Dispos. 38 , 2302-8, (2010)

Drug-induced liver injury (DILI) is one of the most important reasons for drug development failure at both preapproval and postapproval stages. There has been increased interest in developing predicti...