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Substance Name: Broxuridine [INN:JAN]
RN: 59-14-3
UNII: G34N38R2N1
InChIKey: WOVKYSAHUYNSMH-RRKCRQDMSA-N

Note

  • A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.

Molecular Formula

  • C9-H11-Br-N2-O5

Molecular Weight

  • 307.099
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic Agents
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Noxae
  • Radiation-Sensitizing Agents
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Bromodeoxyuridine
  • Broxuridine
  • Broxuridine [INN:JAN]

MeSH Heading

  • Bromodeoxyuridine

Synonyms

  • 4-24-00-01234 (Beilstein Handbook Reference)
  • 5-Bdu
  • 5-Bromo-2'-deoxyuridine
  • 5-Bromodeoxyuridine
  • 5-Bromodesoxyuridine
  • 5-Bromouracil deoxyriboside
  • 5-Bromouracil-2-deoxyriboside
  • 5-Budr
  • BDU
  • BRN 0030395
  • Bromodeoxyuridine
  • Bromoouridine
  • Bromouracil deoxyriboside
  • Broxuridina
  • Broxuridina [INN-Spanish]
  • Broxuridine
  • Broxuridinum
  • Broxuridinum [INN-Latin]
  • Brudr
  • BUDR
  • CCRIS 818
  • EINECS 200-415-9
  • HSDB 7477
  • NSC 38297
  • NSC-38297
  • Radibud
  • UNII-G34N38R2N1

Systematic Names

  • 5-Bromo-2'-deoxyuridine
  • 5-Bromodeoxyuridine
  • Broxuridine
  • Uridine, 5-bromo-2'-deoxy-

Registry Numbers

CAS Registry Number

  • 59-14-3

FDA UNII

  • G34N38R2N1

Other Registry Numbers

  • 1236362-78-9
  • 3445-26-9
  • 723-73-9

System Generated Number

  • 0000059143

Structure Descriptors

InChI

1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChIKey

WOVKYSAHUYNSMH-RRKCRQDMSA-N

Smiles

n1([C@@H]2O[C@H](CO)[C@H](C2)O)c([nH]c(=O)c(c1)Br)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3050mg/kg (3050mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: PULSE RATE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
mouse LD50 intravenous 2500mg/kg (2500mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: PULSE RATE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
mouse LD50 oral 9100mg/kg (9100mg/kg)   Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
mouse LD50 oral 9100mg/kg (9100mg/kg) BLOOD: CHANGES IN SPLEEN

BEHAVIORAL: MUSCLE WEAKNESS
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
mouse LD50 subcutaneous 3500mg/kg (3500mg/kg) CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
quail LD50 oral > 100mg/kg (100mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intraperitoneal 1500mg/kg (1500mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 2320mg/kg (2320mg/kg) VASCULAR: OTHER CHANGES Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 735, 1971.
rat LD50 oral 8400mg/kg (8400mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 467, 1973.
rat LD50 subcutaneous 3900mg/kg (3900mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 30, Pg. 530, 1971.
rat LD50 unreported 2300mg/kg (2300mg/kg)   Drugs in Japan Vol. 6, Pg. 721, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 192.5 deg C   EXP
log P (octanol-water) -0.29 (none)   EXP
Water Solubility 967 mg/L 25 EST
Vapor Pressure 4.73E-15 mm Hg 25 EST
Henry's Law Constant 1.54E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.82E-11 cm3/molecule-sec 25 EST

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