Razoxane | CAS#21416-67-1 | Immunosuppressant

MedKoo Cat#: 592299 | Name: Razoxane

Featured

Description:

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

Razoxane, also known as ICRF 159, is an antimitotic agent with immunosuppressive properties. Razoxane demonstrated high potency against angiogenesis and metastasis. Razoxane inhibits topoisomerase II without inducing DNA strand breaks. Razoxane is an antimitotic agent with immunosuppressive properties. Razoxane inhibits blood-borne and lymphatic metastases in different experimental models.

Chemical Structure

Razoxane

CAS#21416-67-1

Theoretical Analysis

MedKoo Cat#: 592299

Name: Razoxane

CAS#: 21416-67-1

Chemical Formula: C11H16N4O4

Exact Mass: 268.1172

Molecular Weight: 268.27

Elemental Analysis: C, 49.25; H, 6.01; N, 20.88; O, 23.85

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00	2 Weeks
25mg	USD 1,000.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Razoxane; ICRF 159; ICRF-159; ICRF159; NSC 129943; NSC-129943; NSC129943, Tepirone; Troxozone;

IUPAC/Chemical Name

2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-

InChi Key

BMKDZUISNHGIBY-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)

SMILES Code

CC(N(C1)CC(NC1=O)=O)CN(C2)CC(NC2=O)=O

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Razoxane is clinically active against angiogenesis and metastasis. Razoxane specifically inhibits topoisomerase II without inducing DNA strand breaks (topo II catalytic inhibitor). It is an antimitotic agent with immunosuppressive properties. Razoxane inhibits blood-borne and lymphatic metastases in different experimental models. Studies have shown that razoxane inhibits specifically the vasculogenic mimicry of B16F10 melanoma cells.

In vitro activity:

Immunolabeling with Crest autoimmune sera, which recognizes centromere proteins, and with MPM-2 monoclonal antibody, which recognizes mitotic phosphoproteins, indicated that the centromeres of the chromosomes assembled a normal metaphase array in the presence of ICRF-187 and Razoxane. Reference: Cancer Res. 1994 Feb 15;54(4):1042-8. https://pubmed.ncbi.nlm.nih.gov/8313360/

In vivo activity:

Razoxane is an antiangiogenic agent that has minimal toxicity and that requires further evaluation in combination with other active agents in the treatment of renal cell carcinoma. Clin Cancer Res. 2000 Dec;6(12):4697-704. https://pubmed.ncbi.nlm.nih.gov/11156222/

	Solvent	mg/mL	mM
Solubility
	DMSO	40.0	149.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 268.27 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.

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

Formulation protocol:

1. Gorbsky GJ. Cell cycle progression and chromosome segregation in mammalian cells cultured in the presence of the topoisomerase II inhibitors ICRF-187 [(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane; ADR-529] and ICRF-159 (Razoxane). Cancer Res. 1994 Feb 15;54(4):1042-8. PMID: 8313360. 2. Rhomberg W, Stephan H, Böhler F, Erhart K, Eiter H. Radiotherapy and razoxane in advanced bile duct carcinomas. Anticancer Res. 2005 Sep-Oct;25(5):3613-8. PMID: 16101189. 3. Braybrooke JP, O'Byrne KJ, Propper DJ, Blann A, Saunders M, Dobbs N, Han C, Woodhull J, Mitchell K, Crew J, Smith K, Stephens R, Ganesan TS, Talbot DC, Harris AL. A phase II study of razoxane, an antiangiogenic topoisomerase II inhibitor, in renal cell cancer with assessment of potential surrogate markers of angiogenesis. Clin Cancer Res. 2000 Dec;6(12):4697-704. PMID: 11156222.

In vitro protocol:

In vivo protocol:

1. Rhomberg W, Stephan H, Böhler F, Erhart K, Eiter H. Radiotherapy and razoxane in advanced bile duct carcinomas. Anticancer Res. 2005 Sep-Oct;25(5):3613-8. PMID: 16101189. 2. Braybrooke JP, O'Byrne KJ, Propper DJ, Blann A, Saunders M, Dobbs N, Han C, Woodhull J, Mitchell K, Crew J, Smith K, Stephens R, Ganesan TS, Talbot DC, Harris AL. A phase II study of razoxane, an antiangiogenic topoisomerase II inhibitor, in renal cell cancer with assessment of potential surrogate markers of angiogenesis. Clin Cancer Res. 2000 Dec;6(12):4697-704. PMID: 11156222.

1: Thirupathi C, Nagesh Kumar K, Srinivasu G, Lakshmi Narayana C, Parameswara Murthy C. Development and Validation of Stereo Selective Method for the Separation of Razoxane Enantiomers in Hydrophilic Interaction Chromatography. J Chromatogr Sci. 2018 Feb 1;56(2):147-153. doi: 10.1093/chromsci/bmx094. PMID: 29140426. 2: Rhomberg W, Wink A, Pokrajac B, Eiter H, Hackl A, Pakisch B, Ginestet A, Lukas P, Pötter R. Treatment of vascular soft tissue sarcomas with razoxane, vindesine, and radiation. Int J Radiat Oncol Biol Phys. 2009 May 1;74(1):187-91. doi: 10.1016/j.ijrobp.2008.06.1492. Epub 2008 Nov 10. PMID: 19004568. 3: Rhomberg W, Eiter H, Schmid F, Saely C. Razoxane and vindesine in advanced soft tissue sarcomas: impact on metastasis, survival and radiation response. Anticancer Res. 2007 Sep-Oct;27(5B):3609-14. PMID: 17972524. 4: Rhomberg W, Eiter H, Schmid F, Saely CH. Combined vindesine and razoxane shows antimetastatic activity in advanced soft tissue sarcomas. Clin Exp Metastasis. 2008;25(1):75-80. doi: 10.1007/s10585-007-9103-9. Epub 2007 Oct 12. PMID: 17932774. 5: Rhomberg W, Hammer J, Sedlmayer F, Eiter H, Seewald D, Schneider B. Irradiation with and without razoxane in the treatment of incompletely resected or inoperable recurrent rectal cancer. Results of a small randomized multicenter study. Strahlenther Onkol. 2007 Jul;183(7):380-4. doi: 10.1007/s00066-007-1617-1. PMID: 17609871. 6: Rhomberg W. The radiation response of sarcomas by histologic subtypes: a review with special emphasis given to results achieved with razoxane. Sarcoma. 2006;2006(1):87367. doi: 10.1155/SRCM/2006/87367. PMID: 17040092; PMCID: PMC1510952. 7: Rhomberg W, Eiter H, Böhler F, Dertinger S. Combined radiotherapy and razoxane in the treatment of chondrosarcomas and chordomas. Anticancer Res. 2006 May-Jun;26(3B):2407-11. PMID: 16821624. 8: Rhomberg W, Stephan H, Böhler F, Erhart K, Eiter H. Radiotherapy and razoxane in advanced bile duct carcinomas. Anticancer Res. 2005 Sep-Oct;25(5):3613-8. PMID: 16101189. 9: Rhomberg W, Eiter H, Boehler F, Saely C, Strohal R. Combined razoxane and radiotherapy for melanoma brain metastases. a retrospective analysis. J Neurooncol. 2005 Sep;74(3):295-9. doi: 10.1007/s11060-004-7557-z. PMID: 16086112. 10: Anderson H, Yap JT, Wells P, Miller MP, Propper D, Price P, Harris AL. Measurement of renal tumour and normal tissue perfusion using positron emission tomography in a phase II clinical trial of razoxane. Br J Cancer. 2003 Jul 21;89(2):262-7. doi: 10.1038/sj.bjc.6601105. PMID: 12865914; PMCID: PMC2394254. 11: Rhomberg W, Böhler FK, Novak H, Dertinger S, Breitfellner G. A small prospective study of chordomas treated with radiotherapy and razoxane. Strahlenther Onkol. 2003 Apr;179(4):249-53. doi: 10.1007/s00066-003-1052-x. PMID: 12707714. 12: Hellmann K. Dynamics of tumour angiogenesis: effect of razoxane-induced growth rate slowdown. Clin Exp Metastasis. 2003;20(2):95-102. doi: 10.1023/a:1022632413888. PMID: 12705630. 13: Braybrooke JP, O'Byrne KJ, Propper DJ, Blann A, Saunders M, Dobbs N, Han C, Woodhull J, Mitchell K, Crew J, Smith K, Stephens R, Ganesan TS, Talbot DC, Harris AL. A phase II study of razoxane, an antiangiogenic topoisomerase II inhibitor, in renal cell cancer with assessment of potential surrogate markers of angiogenesis. Clin Cancer Res. 2000 Dec;6(12):4697-704. PMID: 11156222. 14: Rhomberg W, Grass M. Angiosarkom des rechten Vorhofs: lokale Kontrolle durch niedrige Strahlendosen und Razoxan. Ein Fallbericht [Angiosarcoma of the right atrium: local control via low radiation doses and razoxane. A case report]. Strahlenther Onkol. 1999 Mar;175(3):102-4. German. doi: 10.1007/BF02742342. PMID: 10093611. 15: Garbisa S, Onisto M, Peron A, Perissin L, Rapozzi V, Zorzet S, Giraldi T. Suppression of metastatic potential and up-regulation of gelatinases and uPA in LLC by protracted in vivo treatment with dacarbazine or razoxane. Int J Cancer. 1997 Sep 17;72(6):1056-61. doi: 10.1002/(sici)1097-0215(19970917)72:6<1056::aid- ijc21>3.0.co;2-1. PMID: 9378540. 16: Rhomberg W, Hassenstein EO, Gefeller D. Radiotherapy vs. radiotherapy and razoxane in the treatment of soft tissue sarcomas: final results of a randomized study. Int J Radiat Oncol Biol Phys. 1996 Dec 1;36(5):1077-84. doi: 10.1016/s0360-3016(96)00433-6. PMID: 8985029. 17: Rhomberg W, Eiter H, Hergan K, Schneider B. Inoperable recurrent rectal cancer: results of a prospective trial with radiation therapy and razoxane. Int J Radiat Oncol Biol Phys. 1994 Sep 30;30(2):419-25. doi: 10.1016/0360-3016(94)90023-x. PMID: 7523346. 18: Gorbsky GJ. Cell cycle progression and chromosome segregation in mammalian cells cultured in the presence of the topoisomerase II inhibitors ICRF-187 [(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane; ADR-529] and ICRF-159 (Razoxane). Cancer Res. 1994 Feb 15;54(4):1042-8. PMID: 8313360. 19: Kingston RD, Fielding JW, Palmer MK. An evaluation of the effectiveness and safety of razoxane when used as an adjunct to surgery in colo-rectal cancer. Report of a controlled randomised study of 603 patients. Int J Colorectal Dis. 1993 Jul;8(2):106-10. doi: 10.1007/BF00299338. PMID: 8409683. 20: Haug IJ, Siebke EM, Grimstad IA, Benestad HB. Simultaneous assessment of migration and proliferation of murine fibrosarcoma cells, as affected by hydroxyurea, vinblastine, cytochalasin B, Razoxane and interferon. Cell Prolif. 1993 May;26(3):251-61. doi: 10.1111/j.1365-2184.1993.tb00023.x. PMID: 7686776.