6-AZAURIDINE

Names

[ CAS No. ]:
54-25-1

[ Name ]:
6-AZAURIDINE

[Synonym ]:
6-azur
AZURIDINE
ribo-azuracil
6-azuridine
6-AZAURIDINE
6-aza-uridine
6-Azauracil Ribozide
MFCD00006472
1,2,4-Triazine-3,5(2H,4H)-dione, 2-β-D-ribofuranosyl-
as-Triazine-3,5(2H,4H)-dione, 2-β-D-ribofuranosyl-
2-(β-D-Ribofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione
6-phosphonouridine 5′-monophosphate
azauridine
azur
EINECS 200-199-6
ribo-Azauracil
2-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2H--[1,2,4]triazine-3,5-dione
2-b-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione

Biological Activity

[Description]:

6-Azuridine (6-Azauridine) is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

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

Research Areas >> Others

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Melting Point ]:
157-159 °C(lit.)

[ Molecular Formula ]:
C₈H₁₁N₃O₆

[ Molecular Weight ]:
245.19

[ Exact Mass ]:
245.064789

[ PSA ]:
137.67000

[ LogP ]:
-1.96

[ Index of Refraction ]:
1.795

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XY8575000

CHEMICAL NAME :: as-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 54-25-1

BEILSTEIN REFERENCE NO. :: 0032281

LAST UPDATED :: 199709

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C8-H11-N3-O6

MOLECULAR WEIGHT :: 245.22

WISWESSER LINE NOTATION :: T6NNVMVJ B- BT5OTJ CQ DQ E1Q

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 :: 9400 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11250 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 :: Intraperitoneal

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 3400 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 :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 2400 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 :: Bird - quail

DOSE/DURATION :: >316 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 gm/kg/32D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Blood - leukopenia Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 150 mg/kg

SEX/DURATION :: female 47 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 84 mg/kg

SEX/DURATION :: female 6-12 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 :: 252 mg/kg

SEX/DURATION :: female 6-12 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 - fetal death Reproductive - Specific Developmental Abnormalities - body wall

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 330 mg/kg

SEX/DURATION :: female 8 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 330 mg/kg

SEX/DURATION :: female 11 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 900 mg/kg

SEX/DURATION :: female 7-9 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 900 mg/kg

SEX/DURATION :: female 12-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 10 gm/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 6250 mg/kg

SEX/DURATION :: female 3-27 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Mutation test systems - not otherwise specified

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

REFERENCE :: CEFYAD Ceskoslovenska Fysiologie. (Academia, Vodickova 40, 112 29 Prague 1, Czechoslovakia) V.1- 1952- Volume(issue)/page/year: 21,278,1972 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332-H351

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XY8575000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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