Tirapazamine
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MedKoo CAT#: 202940

CAS#: 27314-97-2

Description: Trapazamine, also known as SR-4233,DNA-damaging drug potentially for the treatment of cervical carcinoma, head and neck cancer. Tirapazamine is activated to its toxic form preferentially in the hypoxic areas of solid tumors. Cells in these regions are resistant to killing by radiotherapy and most anticancer drugs. Thus the combination of tirapazamine with conventional anticancer treatments is particularly effective.


Chemical Structure

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Tirapazamine
CAS# 27314-97-2

Theoretical Analysis

MedKoo Cat#: 202940
Name: Tirapazamine
CAS#: 27314-97-2
Chemical Formula: C7H6N4O2
Exact Mass: 178.04908
Molecular Weight: 178.15
Elemental Analysis: C, 47.19; H, 3.39; N, 31.45; O, 17.96

Price and Availability

Size Price Availability Quantity
50.0mg USD 250.0 2 Weeks
100.0mg USD 450.0 2 Weeks
200.0mg USD 650.0 2 Weeks
500.0mg USD 1250.0 2 Weeks
1.0g USD 1750.0 2 Weeks
2.0g USD 2650.0 2 Weeks
5.0g USD 3950.0 2 Weeks
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Synonym: Tirapazamine; Tirazone; SR 4233; SR-4233; SR4233; SR259075; SR-259075; SR 259075; WIN 59075; NSC130181.

IUPAC/Chemical Name: 3-aminobenzo[e][1,2,4]triazine 1,4-dioxide

InChi Key: ORYDPOVDJJZGHQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)

SMILES Code: NC1=[N+]([O-])C2=CC=CC=C2[N+]([O-])=N1

Appearance: Orange to dark orange-red solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 178.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Reddy SB, Williamson SK. Tirapazamine: a novel agent targeting hypoxic tumor cells. Expert Opin Investig Drugs. 2009 Jan;18(1):77-87. doi: 10.1517/13543780802567250 . Review. PubMed PMID: 19053884.

2: Marcu L, Olver I. Tirapazamine: from bench to clinical trials. Curr Clin Pharmacol. 2006 Jan;1(1):71-9. Review. PubMed PMID: 18666379.

3: Gandara DR, Lara PN Jr, Goldberg Z, Le QT, Mack PC, Lau DH, Gumerlock PH. Tirapazamine: prototype for a novel class of therapeutic agents targeting tumor hypoxia. Semin Oncol. 2002 Feb;29(1 Suppl 4):102-9. Review. PubMed PMID: 11894020.

4: Denny WA, Wilson WR. Tirapazamine: a bioreductive anticancer drug that exploits tumour hypoxia. Expert Opin Investig Drugs. 2000 Dec;9(12):2889-901. Review. PubMed PMID: 11093359.

5: Patterson AV, Saunders MP, Chinje EC, Patterson LH, Stratford IJ. Enzymology of tirapazamine metabolism: a review. Anticancer Drug Des. 1998 Sep;13(6):541-73. Review. PubMed PMID: 9755718.

6: Brown JM, Wang LH. Tirapazamine: laboratory data relevant to clinical activity. Anticancer Drug Des. 1998 Sep;13(6):529-39. Review. PubMed PMID: 9755717.

7: Gatzemeier U, Rodriguez G, Treat J, Miller V, von Roemeling R, Viallet J, Rey A. Tirapazamine-cisplatin: the synergy. Br J Cancer. 1998 Jun;77 Suppl 4:15-7. Review. PubMed PMID: 9647615; PubMed Central PMCID: PMC2149886.

8: Brown JM. Exploiting tumour hypoxia and overcoming mutant p53 with tirapazamine. Br J Cancer. 1998 Jun;77 Suppl 4:12-4. Review. PubMed PMID: 9647614; PubMed Central PMCID: PMC2149884.

9: Brown JM. SR 4233 (tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours. Br J Cancer. 1993 Jun;67(6):1163-70. Review. PubMed PMID: 8512801; PubMed Central PMCID: PMC1968495.