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 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL207990 ;
PubChem CID	16760412 ;
UNII	Y0900I3U8U ;
CompTox Dashboard (EPA)	DTXSID5044073 ;
	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	554.729 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).
	verify (what is ?)
	Infobox references

Last updated June 26, 2020

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.

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Carfilzomib is an anti-cancer drug acting as a selective proteasome inhibitor. Chemically, it is a tetrapeptide epoxyketone and an analog of epoxomicin.

References

↑ Epoxomicin, Santa Cruz Biotechnology
↑ 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.
↑ Epoxomicin, Peptide Institute, Inc.

Hanada, M; Sugawara, K; Kaneta, K; Toda, S; Nishiyama, Y; Tomita, K; Yamamoto, H; Konishi, M; Oki, T (November 1992). "Epoxomicin, a new antitumor agent of microbial origin". J. Antibiot. 45 (11): 1746–52. 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 (18): 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.

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[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.

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 ^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL207990 ^N
PubChem CID	16760412
UNII	Y0900I3U8U ^Y
CompTox Dashboard (EPA)	DTXSID5044073
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	554.729 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).
N verify (what is ^YN ?)
Infobox references

Epoxomicin

Related Research Articles

References

Further reading