XR-5000

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

MedKoo CAT#: 206744

CAS#: 89459-25-6

Description: XR-5000, also known as DACA and SN 22995, is a DNA topoisomerase I and II inhibitor potentially for the treatment of colorectal cancer, glioblastoma. Topoisomerases I and II unravel DNA during transcription, DNA replication and DNA repair. Inhibitors of both enzymes are important anticancer drugs, but only now are combined inhibitors becoming available for clinical use.


Price and Availability

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XR-5000 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

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Theoretical Analysis

MedKoo Cat#: 206744
Name: XR-5000
CAS#: 89459-25-6
Chemical Formula: C18H19N3O
Exact Mass: 293.1528
Molecular Weight: 293.37
Elemental Analysis: C, 73.69; H, 6.53; N, 14.32; O, 5.45


Synonym: CRC-8805; DACA; NSC-601316; SN-22995; XR-5000; CRC8805; NS-601316; SN22995; XR5000.

IUPAC/Chemical Name: N-(2-(Dimethylamino)ethyl)-4-acridinecarboxamide

InChi Key: XBGNERSKEKDZDS-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H19N3O/c1-21(2)11-10-19-18(22)15-8-5-7-14-12-13-6-3-4-9-16(13)20-17(14)15/h3-9,12H,10-11H2,1-2H3,(H,19,22)

SMILES Code: O=C(C1=CC=CC2=CC3=CC=CC=C3N=C12)NCCN(C)C


Technical Data

Appearance:
Light brown to brown 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: Soo JC, Lee EG, Lee LA, Kashon ML, Harper M. Evaluation of pump pulsation in respirable size-selective sampling: Part III. Investigation of European standard methods. Ann Occup Hyg. 2014 Oct;58(8):1006-17. doi: 10.1093/annhyg/meu047. PubMed PMID: 25053700; PubMed Central PMCID: PMC4702258.

2: Saleem A, Aboagye EO, Matthews JC, Price PM. Plasma pharmacokinetic evaluation of cytotoxic agents radiolabelled with positron emitting radioisotopes. Cancer Chemother Pharmacol. 2008 Apr;61(5):865-73. PubMed PMID: 17639391.

3: Gilroy KL, Leontiou C, Padget K, Lakey JH, Austin CA. mAMSA resistant human topoisomerase IIbeta mutation G465D has reduced ATP hydrolysis activity. Nucleic Acids Res. 2006 Mar 20;34(5):1597-607. PubMed PMID: 16549872; PubMed Central PMCID: PMC1405819.

4: Dittrich C, Dieras V, Kerbrat P, Punt C, Sorio R, Caponigro F, Paoletti X, de Balincourt C, Lacombe D, Fumoleau P. Phase II study of XR5000 (DACA), an inhibitor of topoisomerase I and II, administered as a 120-h infusion in patients with advanced ovarian cancer. Invest New Drugs. 2003 Aug;21(3):347-52. PubMed PMID: 14578683.

5: Baguley BC, Wakelin LP, Jacintho JD, Kovacic P. Mechanisms of action of DNA intercalating acridine-based drugs: how important are contributions from electron transfer and oxidative stress? Curr Med Chem. 2003 Dec;10(24):2643-9. Review. PubMed PMID: 14529454.

6: Dittrich C, Coudert B, Paz-Ares L, Caponigro F, Salzberg M, Gamucci T, Paoletti X, Hermans C, Lacombe D, Fumoleau P; European Organization for Research and Treatment of Cancer--Early Clinical Studies Group/New Drug Development Programme (EORTC-ECSG/NDDP).. Phase II study of XR 5000 (DACA), an inhibitor of topoisomerase I and II, administered as a 120-h infusion in patients with non-small cell lung cancer. Eur J Cancer. 2003 Feb;39(3):330-4. PubMed PMID: 12565985.

7: Cree IA. Chemosensitivity testing as an aid to anti-cancer drug and regimen development. Recent Results Cancer Res. 2003;161:119-25. Review. PubMed PMID: 12528804.

8: Propper DJ, de Bono J, Saleem A, Ellard S, Flanagan E, Paul J, Ganesan TS, Talbot DC, Aboagye EO, Price P, Harris AL, Twelves C. Use of positron emission tomography in pharmacokinetic studies to investigate therapeutic advantage in a phase I study of 120-hour intravenous infusion XR5000. J Clin Oncol. 2003 Jan 15;21(2):203-10. Erratum in: J Clin Oncol. 2003 Aug 1;21(15):3006. PubMed PMID: 12525511.

9: Twelves C, Campone M, Coudert B, Van den Bent M, de Jonge M, Dittrich C, Rampling R, Sorio R, Lacombe D, de Balincourt C, Fumoleau P; European Organisation for Research and Treatment of Cancer-Early Clinical Studies Group/New Drug Development Programme.. Phase II study of XR5000 (DACA) administered as a 120-h infusion in patients with recurrent glioblastoma multiforme. Ann Oncol. 2002 May;13(5):777-80. PubMed PMID: 12075748.

10: Caponigro F, Dittrich C, Sorensen JB, Schellens JH, Duffaud F, Paz Ares L, Lacombe D, de Balincourt C, Fumoleau P. Phase II study of XR 5000, an inhibitor of topoisomerases I and II, in advanced colorectal cancer. Eur J Cancer. 2002 Jan;38(1):70-4. PubMed PMID: 11750842.

11: Saleem A, Harte RJ, Matthews JC, Osman S, Brady F, Luthra SK, Brown GD, Bleehen N, Connors T, Jones T, Price PM, Aboagye EO. Pharmacokinetic evaluation of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide in patients by positron emission tomography. J Clin Oncol. 2001 Mar 1;19(5):1421-9. PubMed PMID: 11230487.

12: Neale MH, Charlton PA, Cree IA. Ex vivo activity of XR5000 against solid tumors. Anticancer Drugs. 2000 Jul;11(6):471-8. PubMed PMID: 11001388.

13: Padget K, Stewart A, Charlton P, Tilby MJ, Austin CA. An investigation into the formation of N- [2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) and 6-[2-(dimethylamino)ethylamino]- 3-hydroxy-7H-indeno[2, 1-C]quinolin-7-one dihydrochloride (TAS-103) stabilised DNA topoisomerase I and II cleavable complexes in human leukaemia cells. Biochem Pharmacol. 2000 Sep 15;60(6):817-21. PubMed PMID: 10930536.

14: Twelves CJ, Gardner C, Flavin A, Sludden J, Dennis I, de Bono J, Beale P, Vasey P, Hutchison C, Macham MA, Rodriguez A, Judson I, Bleehen NM. Phase I and pharmacokinetic study of DACA (XR5000): a novel inhibitor of topoisomerase I and II. CRC Phase I/II Committee. Br J Cancer. 1999 Aug;80(11):1786-91. PubMed PMID: 10468297; PubMed Central PMCID: PMC2363132.