XR-11576

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

MedKoo CAT#: 591663

CAS#: 346689-77-8

Description: XR-11576, is a DNA topoisomerase I and II inhibitor used for the treatment of solid tumors.


Price and Availability

Size
Price

Size
Price

Size
Price

XR-11576 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 591663
Name: XR-11576
CAS#: 346689-77-8
Chemical Formula: C23H24N4O2
Exact Mass: 388.1899
Molecular Weight: 388.47
Elemental Analysis: C, 71.11; H, 6.23; N, 14.42; O, 8.24


Synonym: XR-11576; XR 11576; XR11576; MLN-576; MLN 576; MLN576;

IUPAC/Chemical Name: (S)-N-(1-(dimethylamino)propan-2-yl)-4-methoxybenzo[a]phenazine-11-carboxamide

InChi Key: ACAXGYADTLFREX-CQSZACIVSA-N

InChi Code: InChI=1S/C23H24N4O2/c1-14(13-27(2)3)24-23(28)17-8-5-9-18-22(17)26-21-16-7-6-10-20(29-4)15(16)11-12-19(21)25-18/h5-12,14H,13H2,1-4H3,(H,24,28)/t14-/m1/s1

SMILES Code: O=C(C1=C2C(N=C3C=CC4=C(OC)C=CC=C4C3=N2)=CC=C1)N[C@@H](C)CN(C)C


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Jobson AG, Willmore E, Tilby MJ, Mistry P, Charlton P, Austin CA. Effect of phenazine compounds XR11576 and XR5944 on DNA topoisomerases. Cancer Chemother Pharmacol. 2009 Apr;63(5):889-901. doi: 10.1007/s00280-008-0812-9. Epub 2008 Aug 5. PubMed PMID: 18679685.

2: Lewis LJ, Mistry P, Charlton PA, Thomas H, Coley HM. Mode of action of the novel phenazine anticancer agents XR11576 and XR5944. Anticancer Drugs. 2007 Feb;18(2):139-48. PubMed PMID: 17159600.

3: Di Nicolantonio F, Knight LA, Di Palma S, Sharma S, Whitehouse PA, Mercer SJ, Charlton PA, Norris D, Cree IA. Ex vivo characterization of XR11576 (MLN576) against ovarian cancer and other solid tumors. Anticancer Drugs. 2004 Oct;15(9):849-60. PubMed PMID: 15457125.

4: de Jonge MJ, Kaye S, Verweij J, Brock C, Reade S, Scurr M, van Doorn L, Verheij C, Loos W, Brindley C, Mistry P, Cooper M, Judson I. Phase I and pharmacokinetic study of XR11576, an oral topoisomerase I and II inhibitor, administered on days 1-5 of a 3-weekly cycle in patients with advanced solid tumours. Br J Cancer. 2004 Oct 18;91(8):1459-65. PubMed PMID: 15452551; PubMed Central PMCID: PMC2409936.

5: Mistry P, Stewart AJ, Dangerfield W, Baker M, Liddle C, Bootle D, Kofler B, Laurie D, Denny WA, Baguley B, Charlton PA. In vitro and in vivo characterization of XR11576, a novel, orally active, dual inhibitor of topoisomerase I and II. Anticancer Drugs. 2002 Jan;13(1):15-28. PubMed PMID: 11914637.

6: Wang S, Miller W, Milton J, Vicker N, Stewart A, Charlton P, Mistry P, Hardick D, Denny WA. Structure-activity relationships for analogues of the phenazine-based dual topoisomerase I/II inhibitor XR11576. Bioorg Med Chem Lett. 2002 Feb 11;12(3):415-8. PubMed PMID: 11814810.

7: Vicker N, Burgess L, Chuckowree IS, Dodd R, Folkes AJ, Hardick DJ, Hancox TC, Miller W, Milton J, Sohal S, Wang S, Wren SP, Charlton PA, Dangerfield W, Liddle C, Mistry P, Stewart AJ, Denny WA. Novel angular benzophenazines: dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents. J Med Chem. 2002 Jan 31;45(3):721-39. PubMed PMID: 11806724.