Epoxomicin

Epoxomicin^[1]

Names
IUPAC name (2S,3S)-N-((2S,3R)-3-hydroxy-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxobutan-2-yl)-3-methyl-2-((2S,3S)-3-methyl-2-(N-methylacetamido)pentanamido)pentanamide
Other names BU 4061T
Identifiers
CAS Number	134381-21-8
ChEMBL	ChEMBL207990
Jmol interactive 3D	Image
PubChem	16760412
SMILES O=C([C@@]1(C)CO1)[C@H](CC(C)C)NC([C@@H](NC([C@H]([C@@H](C)CC)NC([C@H]([C@@H](C)CC)N(C)C(C)=O)=O)=O)[C@H](O)C)=O
Properties
Chemical formula	C28H50N4O7
Molar mass	554.73 g·mol^−1
Appearance	White solid
Solubility in DMSO	10 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Epoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.^[2] It was originally discovered in 1992.^[3] Injected, it can induce Parkinson's-like symptoms in rats.

Derivatives of epoxomicin include carfilzomib.

References

1. Epoxomicin, Santa Cruz Biotechnology
2. Meng, L; Mohan, R; Kwok, BH; Elofsson, M; Sin, N; Crews, CM (1999). "Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity". PNAS 96 (18): 10403–10408. doi:10.1073/pnas.96.18.10403. PMC 17900. PMID 10468620.
3. Epoxomicin, Peptide Institute, Inc.

Further reading

• "Epoxomicin, a new antitumor agent of microbial origin". J. Antibiot. 45 (11): 1746–52. November 1992. doi:10.7164/antibiotics.45.1746. PMID 1468981.
• Meng, L.; et al. (1999). "Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity". Proc. Natl. Acad. Sci. U.S.A 96: 10403–10408. doi:10.1073/pnas.96.18.10403. PMC 17900. PMID 10468620.
• Schwarz, K.; et al. (2000). "The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up- or down-regulate antigen presentation at nontoxic doses". J. Immunol 164 (12): 6147–6157. doi:10.4049/jimmunol.164.12.6147. PMC 2507740. PMID 10843664.
• Princiotta, M.F.; et al. (2001). "Cells adapted to the proteasome inhibitor 4-hydroxy- 5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone require enzymatically active proteasomes for continued survival". Proc. Natl. Acad. Sci. U.S.A 98 (2): 513–518. doi:10.1073/pnas.021132398. PMC 14618. PMID 11149939.
• Garrett, I.R.; et al. (2003). "Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro". J. Clin. Invest 111 (11): 1771–1782. doi:10.1172/JCI16198. PMC 156102. PMID 12782679.
• McNaught, K.S.; et al. (2004). "Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease". Annals of Neurology 56 (1): 149–162. doi:10.1002/ana.20186. PMID 15236415.