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Tirapazamine
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  • Name Tirapazamine
  • EINECS636-678-5
  • CAS No. 27314-97-2
  • Density1.68 g/cm3
  • PSA89.83000
  • LogP1.25520
  • SolubilityN/A
  • Melting Point220 °C dec.
  • FormulaC7H6N4O2
  • Boiling Point493.6 °C at 760 mmHg
  • Molecular Weight178.15
  • Flash Point252.3 °C
  • Transport InformationN/A
  • AppearanceOrange needles
  • Safety26-36
  • Risk Codes36/37/38
  • Molecular Structure
    Molecular Structure of 27314-97-2 (3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE)
  • Hazard SymbolsIrritantXi
  • SynonymsIrritantXi
  • Article Data22

Tirapazamine Chemical Properties

The Molecular Structure of 1,2,4-Benzotriazin-3-amine, 1,4-dioxide (CAS NO.27314-97-2):

Empirical Formula: C7H6N4O2
Molecular Weight: 178.1481 
IUPAC: 4-hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine 
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals 
Appearance: Orange Needles
Nominal Mass: 178 Da
Average Mass: 178.1481 Da
Monoisotopic Mass: 178.049075 Da 
Index of Refraction: 1.777
Molar Refractivity: 44.288 cm3
Molar Volume: 105.859 cm3
Surface Tension: 85.105 dyne/cm
Density: 1.683 g/cm3
Flash Point: 252.309 °C
Enthalpy of Vaporization: 76.075 kJ/mol
Boiling Point: 493.581 °C at 760 mmHg
Melting Point: 220°C dec.
Storage temp: 2-8°C
Vapour Pressure: 0 mmHg at 25°C 
InChI
InChI=1/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
Smiles
c12c([n+](nc([n+]1[O-])N)[O-])cccc2

Tirapazamine Uses

 1,2,4-Benzotriazin-3-amine, 1,4-dioxide (CAS NO.27314-97-2) can be used as a bioreductive anticancer agent and an antineoplastic.

Tirapazamine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 89mg/kg (89mg/kg)   International Journal of Radiation Oncology, Biology, Physics. Vol. 16, Pg. 977, 1989.
Link to PubMed
mouse LD50 intravenous 101mg/kg (101mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 British Journal of Cancer, Supplement. Vol. 20, Pg. 84, 1993.
rat LD intravenous > 36mg/kg (36mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

ENDOCRINE: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Toxicologist. Vol. 12, Pg. 154, 1992.
rat LD50 intraperitoneal 59390ug/kg (59.39mg/kg)   Archives of Toxicology. Vol. 66, Pg. 100, 1992.
Link to PubMed

Tirapazamine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
RTECS: DM0671500

Tirapazamine Specification

 1,2,4-Benzotriazin-3-amine, 1,4-dioxide (CAS NO.27314-97-2) is also called as Tirapazamine ; Tirapazamine [USAN:INN] ; 3-Amino-1,2,4-benzotriazine 1,4-dioxide ; 3-Amino-1,2,4-benzotriazine-1,4-dioxide ; 4-26-00-01120 (Beilstein Handbook Reference) ; BRN 0179322 ; SR 4233 ; Tirapazamine ; UNII-1UD32YR59G ; WIN 59075 ; 1,2,4-Benzotriazine, 3-amino-, 1,4-dioxide .

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