Oxanthrazole

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584942

CAS#: 118201-50-6

Description: Oxanthrazole has antitumor properties.


Chemical Structure

img
Oxanthrazole
CAS# 118201-50-6

Theoretical Analysis

MedKoo Cat#: 584942
Name: Oxanthrazole
CAS#: 118201-50-6
Chemical Formula: C21H26ClN5O4
Exact Mass: 447.1673
Molecular Weight: 447.92
Elemental Analysis: C, 56.31; H, 5.85; Cl, 7.91; N, 15.64; O, 14.29

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Oxanthrazole; Anthrapyrazole (type)

IUPAC/Chemical Name: Anthra(1,9-cd)pyrazol-6(2H)-one, 5-((3-aminopropyl)amino)-7,10-dihydroxy-2-(2-((2-hydroxyethyl)amino)ethyl)-, hydrochloride

InChi Key: VPNCYQLYSZKURZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H25N5O4.ClH/c22-6-1-7-24-12-2-3-13-17-16(12)21(30)19-15(29)5-4-14(28)18(19)20(17)25-26(13)10-8-23-9-11-27;/h2-5,23-24,27-29H,1,6-11,22H2;1H

SMILES Code: O=C1C2=C3C(N(CCNCCO)N=C3C4=C1C(O)=CC=C4O)=CC=C2NCCCN.[H]Cl

Appearance: 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

Shelf Life: >3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 447.92 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Clark MP, Leaman DW, Hazelhurst LA, Hwang ES, Quinn A. An aza-anthrapyrazole negatively regulates Th1 activity and suppresses experimental autoimmune encephalomyelitis. Int Immunopharmacol. 2016 Feb;31:74-87. doi: 10.1016/j.intimp.2015.12.014. Epub 2015 Dec 18. PubMed PMID: 26709219.

2: Simpkins H, Figliomeni M, Rosen M. The interaction of platinum and anthrapyrazole antitumor drugs with mouse thymocytes studied by terbium fluorescence. Biochim Biophys Acta. 1988 Oct 28;972(1):25-32. PubMed PMID: 2846072.

3: Myers CE. Anthracyclines. Cancer Chemother Biol Response Modif. 1992;13:45-52. Review. PubMed PMID: 1389917.

4: Begleiter A, Lin D, Larson KK, Lang J, Wu X, Cabral T, Taylor H, Guziec LJ, Kerr PD, Hasinoff BB, Guziec FS Jr. Structure-activity studies with cytotoxic anthrapyrazoles. Oncol Rep. 2006 Jun;15(6):1575-80. PubMed PMID: 16685398.

5: Kaye SB, Workman P, Graham MA, Cassidy J, Jodrell D. Pharmacokinetics and early clinical studies of selected new drugs. Cancer Surv. 1993;17:371-96. Review. PubMed PMID: 8137348.

6: Kiraly A, Koffman B, Hacker M, Gunning W, Rasche S, Quinn A. A novel aza-anthrapyrazole blocks the progression of experimental autoimmune encephalomyelitis after the priming of autoimmunity. Clin Immunol. 2011 Dec;141(3):304-16. doi: 10.1016/j.clim.2011.08.009. Epub 2011 Aug 30. PubMed PMID: 21964417.

7: Judson IR. Anthrapyrazoles: true successors to the anthracyclines? Anticancer Drugs. 1991 Jun;2(3):223-31. Review. PubMed PMID: 1802016.

8: Zhang R, Wu X, Yalowich JC, Hasinoff BB. Design, synthesis, and biological evaluation of a novel series of bisintercalating DNA-binding piperazine-linked bisanthrapyrazole compounds as anticancer agents. Bioorg Med Chem. 2011 Dec 1;19(23):7023-32. doi: 10.1016/j.bmc.2011.10.012. Epub 2011 Oct 14. PubMed PMID: 22041173; PubMed Central PMCID: PMC3212645.

9: Fry DW. Biochemical pharmacology of anthracenediones and anthrapyrazoles. Pharmacol Ther. 1991 Oct;52(1):109-25. Review. PubMed PMID: 1666677.

10: D'Incalci M, Capranico G, Giaccone G, Zunino F, Garattini S. DNA topoisomerase inhibitors. Cancer Chemother Biol Response Modif. 1993;14:61-85. Review. PubMed PMID: 8312123.

11: Judson IR. The anthrapyrazoles: a new class of compounds with clinical activity in breast cancer. Semin Oncol. 1992 Dec;19(6):687-94. Review. PubMed PMID: 1462167.

12: Berg SL. Status of new anthrapyrazole and pyrazoloacridine derivatives. Crit Rev Oncol Hematol. 1996 Mar;22(2):79-87. Review. PubMed PMID: 8679102.

13: Sissi C, Palumbo M. Antitumor potential of aza-bioisosterism in anthracenedione-based drugs. Curr Top Med Chem. 2004;4(2):219-30. Review. PubMed PMID: 14754455.

14: Ogawa M, Ariyoshi Y. [New anthracyclines]. Gan To Kagaku Ryoho. 1993 Jan;20(1):27-33. Review. Japanese. PubMed PMID: 8422185.

15: Wang J, Zhao H, Luo Z, Wang Z, Zhang Y, Zhao J. Synthesis and biological activity of anthrapyrazoles derivatives as potential antitumor agents. Med Chem. 2014;10(8):772-7. PubMed PMID: 24773347.

16: Hawkins MJ. New anticancer agents: taxol, camptothecin analogs, and anthrapyrazoles. Oncology (Williston Park). 1992 Dec;6(12):17-23; discussion 27-30. Review. Erratum in: Oncology (Huntingt) 1993 Mar;7(3):105. PubMed PMID: 1361358.

17: Fiebig HH, Berger DP, Winterhalter BR, Plowman J. In vitro and in vivo evaluation of US-NCI compounds in human tumor xenografts. Cancer Treat Rev. 1990 Sep;17(2-3):109-17. PubMed PMID: 2272027.

18: Chou KM, Paul Krapcho A, Hacker MP. Impact of the basic amine on the biological activity and intracellular distribution of an aza-anthrapyrazole: BBR 3422. Biochem Pharmacol. 2001 Nov 15;62(10):1337-43. PubMed PMID: 11709193.

19: Klohs WD, Steinkampf RW. Possible link between the intrinsic drug resistance of colon tumors and a detoxification mechanism of intestinal cells. Cancer Res. 1988 Jun 1;48(11):3025-30. PubMed PMID: 3365692.

20: Chen KX, Gresh N, Pullman B. A theoretical study of the intercalative binding of the anti-tumour drug anthrapyrazole to double-stranded oligonucleotides. Anticancer Drug Des. 1987 Aug;2(1):79-84. PubMed PMID: 3482353.