WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201650
CAS#: 1032119-44-0
Description: KOS-1584 is a second-generation epothilone with potential antineoplastic activity. Epothilone KOS-1584 binds to tubulin and induces microtubule polymerization and stabilizes microtubules against depolymerization, which may result in the inhibition of cell division, the induction of G2/M arrest, and apoptosis. Compared to first-generation epothilones, this agent exhibits greater safety and efficacy with an enhanced pharmaceutical profile, including enhanced water solubility and tumor penetration, and reduced CNS exposure. In addition, epothilone KOS-1584 is a poor substrate for the P-glycoprotein (P-gp) drug efflux pump.
MedKoo Cat#: 201650
Name: KOS-1584
CAS#: 1032119-44-0
Chemical Formula: C27H39NO5S
Exact Mass: 489.25489
Molecular Weight: 489.67
Elemental Analysis: C, 66.23; H, 8.03; N, 2.86; O, 16.34; S, 6.55
Synonym: KOS-1584; KOS 1584; KOS1584; R1645; R=1645; R 1645 9,10-didehydroepothilone D.
IUPAC/Chemical Name: (4S,7R,8R,9S,10Z,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadeca-10,13-diene-2,6-dione
InChi Key: XAYAKDZVINDZGB-PXGYNAETSA-N
InChi Code: InChI=1S/C27H39NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h8,10-11,13,15,17,19,22-23,25,29,31H,9,12,14H2,1-7H3/b10-8-,16-11-,18-13+/t17-,19+,22-,23-,25+/m0/s1
SMILES Code: O=C(C[C@H](O)C1(C)C)O[C@H](/C(C)=C/C2=CSC(C)=N2)C/C=C(C)\C/C=C\[C@H](C)[C@@H](O)[C@@H](C)C1=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). 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, not soluble in water.
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 489.67 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 |
1: Cheng KL, Bradley T, Budman DR. Novel microtubule-targeting agents - the epothilones. Biologics. 2008 Dec;2(4):789-811. PubMed PMID: 19707459; PubMed Central PMCID: PMC2727900.
2: Cigler T, Vahdat L. Integrating epothilones into the treatment of patients with metastatic breast cancer: clinical perspectives on incorporating recent data in the practice setting. Clin Breast Cancer. 2008 Dec;8 Suppl 4:S166-70. Review. PubMed PMID: 19158037.
3: Lee JJ, Kelly WK. Epothilones: tubulin polymerization as a novel target for prostate cancer therapy. Nat Clin Pract Oncol. 2009 Feb;6(2):85-92. Epub 2008 Dec 2. Review. PubMed PMID: 19048010.
4: Trivedi M, Budihardjo I, Loureiro K, Reid TR, Ma JD. Epothilones: a novel class of microtubule-stabilizing drugs for the treatment of cancer. Future Oncol. 2008 Aug;4(4):483-500. Review. PubMed PMID: 18684060.
5: Donovan D, Vahdat LT. Epothilones: clinical update and future directions. Oncology (Williston Park). 2008 Apr 15;22(4):408-16; discussion 416, 421, 424 passim. Review. PubMed PMID: 18472615.
6: Vahdat LT. Clinical studies with epothilones for the treatment of metastatic breast cancer. Semin Oncol. 2008 Apr;35(2 Suppl 2):S22-30; quiz S40. Review. PubMed PMID: 18410796.
7: Burris HA 3rd. Preclinical investigations with epothilones in breast cancer models. Semin Oncol. 2008 Apr;35(2 Suppl 2):S15-21; quiz S39. Review. PubMed PMID: 18410795.
8: Vahdat L. Ixabepilone: a novel antineoplastic agent with low susceptibility to multiple tumor resistance mechanisms. Oncologist. 2008 Mar;13(3):214-21. Review. PubMed PMID: 18378531.
9: Pronzato P. New therapeutic options for chemotherapy-resistant metastatic breast cancer: the epothilones. Drugs. 2008;68(2):139-46. Review. PubMed PMID: 18197722.
10: Fumoleau P, Coudert B, Isambert N, Ferrant E. Novel tubulin-targeting agents: anticancer activity and pharmacologic profile of epothilones and related analogues. Ann Oncol. 2007 Jul;18 Suppl 5:v9-15. Review. PubMed PMID: 17656562.
(last updated: 4/21/2016).
