Rebimastat

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

MedKoo CAT#: 205991

CAS#: 259188-38-0

Description: Rebimastat, also known as BMS275291, is a sulfhydryl-based second-generation matrix metalloproteinase (MMP) inhibitor with potential antineoplastic activity. Rebimastat selectively inhibits several MMPs (MMP 1, 2, 8, 9, and 14), thereby inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis.


Price and Availability

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Rebimastat 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#: 205991
Name: Rebimastat
CAS#: 259188-38-0
Chemical Formula: C23H41N5O5S
Exact Mass: 499.28284
Molecular Weight: 499.67
Elemental Analysis: C, 55.29; H, 8.27; N, 14.02; O, 16.01; S, 6.42


Synonym: Rebimastat; BMS275291; BMS 275291; BMS-275291.

IUPAC/Chemical Name: (S)-N-((S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl)-2-((S)-2-mercapto-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butanamido)-N,4-dimethylpentanamide

SMILES Code: CC(C)C[C@H](NC([C@@H](S)CCN(C(N(C)C1(C)C)=O)C1=O)=O)C(N([C@@H](C(C)(C)C)C(N)=O)C)=O


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:
>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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Brinker BT, Krown SE, Lee JY, Cesarman E, Chadburn A, Kaplan LD, Henry DH, Von Roenn JH. Phase 1/2 trial of BMS-275291 in patients with human immunodeficiency virus-related Kaposi sarcoma: a multicenter trial of the AIDS Malignancy Consortium. Cancer. 2008 Mar 1;112(5):1083-8. doi: 10.1002/cncr.23108. PubMed PMID: 18224669.

2: Lara PN Jr, Stadler WM, Longmate J, Quinn DI, Wexler J, Van Loan M, Twardowski P, Gumerlock PH, Vogelzang NJ, Vokes EE, Lenz HJ, Doroshow JH, Gandara DR. A randomized phase II trial of the matrix metalloproteinase inhibitor BMS-275291 in hormone-refractory prostate cancer patients with bone metastases. Clin Cancer Res. 2006 Mar 1;12(5):1556-63. PubMed PMID: 16533781.

3: Leighl NB, Paz-Ares L, Douillard JY, Peschel C, Arnold A, Depierre A, Santoro A, Betticher DC, Gatzemeier U, Jassem J, Crawford J, Tu D, Bezjak A, Humphrey JS, Voi M, Galbraith S, Hann K, Seymour L, Shepherd FA. Randomized phase III study of matrix metalloproteinase inhibitor BMS-275291 in combination with paclitaxel and carboplatin in advanced non-small-cell lung cancer: National Cancer Institute of Canada-Clinical Trials Group Study BR.18. J Clin Oncol. 2005 Apr 20;23(12):2831-9. PubMed PMID: 15837997.

4: Douillard JY, Peschel C, Shepherd F, Paz-Ares L, Arnold A, Davis M, Tonato M, Smylie M, Tu D, Voi M, Humphrey J, Ottaway J, Young K, Vreckem AV, Seymour L. Randomized phase II feasibility study of combining the matrix metalloproteinase inhibitor BMS-275291 with paclitaxel plus carboplatin in advanced non-small cell lung cancer. Lung Cancer. 2004 Dec;46(3):361-8. PubMed PMID: 15541822.

5: Miller KD, Saphner TJ, Waterhouse DM, Chen TT, Rush-Taylor A, Sparano JA, Wolff AC, Cobleigh MA, Galbraith S, Sledge GW. A randomized phase II feasibility trial of BMS-275291 in patients with early stage breast cancer. Clin Cancer Res. 2004 Mar 15;10(6):1971-5. PubMed PMID: 15041714.

6: Rizvi NA, Humphrey JS, Ness EA, Johnson MD, Gupta E, Williams K, Daly DJ, Sonnichsen D, Conway D, Marshall J, Hurwitz H. A phase I study of oral BMS-275291, a novel nonhydroxamate sheddase-sparing matrix metalloproteinase inhibitor, in patients with advanced or metastatic cancer. Clin Cancer Res. 2004 Mar 15;10(6):1963-70. PubMed PMID: 15041713.

7: Lockhart AC, Braun RD, Yu D, Ross JR, Dewhirst MW, Humphrey JS, Thompson S, Williams KM, Klitzman B, Yuan F, Grichnik JM, Proia AD, Conway DA, Hurwitz HI. Reduction of wound angiogenesis in patients treated with BMS-275291, a broad spectrum matrix metalloproteinase inhibitor. Clin Cancer Res. 2003 Feb;9(2):586-93. PubMed PMID: 12576422.

8: Rundhaug JE. Matrix metalloproteinases, angiogenesis, and cancer: commentary re: A. C. Lockhart et al., Reduction of wound angiogenesis in patients treated with BMS-275291, a broad spectrum matrix metalloproteinase inhibitor. Clin. Cancer Res., 9: 00-00, 2003. Clin Cancer Res. 2003 Feb;9(2):551-4. Review. PubMed PMID: 12576417.

9: Poulaki V. BMS-275291. Bristol-Myers Squibb. Curr Opin Investig Drugs. 2002 Mar;3(3):500-4. Review. PubMed PMID: 12054103.

10: Naglich JG, Jure-Kunkel M, Gupta E, Fargnoli J, Henderson AJ, Lewin AC, Talbott R, Baxter A, Bird J, Savopoulos R, Wills R, Kramer RA, Trail PA. Inhibition of angiogenesis and metastasis in two murine models by the matrix metalloproteinase inhibitor, BMS-275291. Cancer Res. 2001 Dec 1;61(23):8480-5. PubMed PMID: 11731431.