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epoxomicin

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 385971556

| Reference=[http://www.scbt.com/datasheet-201298-epoxomicin.html Epoxomicin], Santa Cruz Biotechnology

| ImageFile = Epoxomicin.svg

| ImageSize = 200px

| ImageAlt =

| IUPACName = (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

| OtherNames = BU 4061T

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 134381-21-8

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 207990

| ChemSpiderID = 9401737

| PubChem = 16760412

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Y0900I3U8U

| StdInChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20?,21?,22?,23?,28+/m0/s1

| StdInChIKey = DOGIDQKFVLKMLQ-BPHQUOOUSA-N

| 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}}

|Section2={{Chembox Properties

| C=28 | H=50 | N=4 | O=7

| Appearance = White solid

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

| SolubleOther = 10 mg/mL

| Solvent = DMSO

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Epoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.{{cite journal | doi = 10.1073/pnas.96.18.10403 | journal = PNAS | year = 1999 | volume = 96 | last1 = Meng | issue = 18 | first1 = L | pages = 10403–10408 | last2 = Mohan | first2 = R | last3 = Kwok | first3 = BH | last4 = Elofsson | first4 = M | last5 = Sin | first5 = N | last6 = Crews | first6 = CM | title = Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity | pmid = 10468620 | pmc = 17900| doi-access = free | bibcode = 1999PNAS...9610403M }} It was originally discovered in 1992.[https://www.peptide.co.jp/en/new-product/314.html Epoxomicin], Peptide Institute, Inc. Injected, it can induce Parkinson's-like symptoms in rats.

Derivatives of epoxomicin include carfilzomib.

References

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Further reading

  • {{cite journal | pmid = 1468981 | volume=45 | issue=11 | title=Epoxomicin, a new antitumor agent of microbial origin |date=November 1992 | journal=J. Antibiot. | pages=1746–52 | doi=10.7164/antibiotics.45.1746| last1=Hanada | first1=M | last2=Sugawara | first2=K | last3=Kaneta | first3=K | last4=Toda | first4=S | last5=Nishiyama | first5=Y | last6=Tomita | first6=K | last7=Yamamoto | first7=H | last8=Konishi | first8=M | last9=Oki | first9=T | doi-access=free }}
  • {{cite journal | last1 = Meng | first1 = L. | year = 1999 | title = Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 96 | issue = 18| pages = 10403–10408 | pmid = 10468620 | doi=10.1073/pnas.96.18.10403 | pmc=17900|display-authors=etal| doi-access = free | bibcode = 1999PNAS...9610403M }}
  • {{cite journal | last1 = Schwarz | first1 = K. | year = 2000 | title = The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up- or down-regulate antigen presentation at nontoxic doses| journal = J. Immunol. | volume = 164 | issue = 12| pages = 6147–6157 | pmid = 10843664 | pmc=2507740 | doi=10.4049/jimmunol.164.12.6147|display-authors=etal}}
  • {{cite journal | last1 = Princiotta | first1 = M.F. | year = 2001 | title = Cells adapted to the proteasome inhibitor 4-hydroxy- 5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone require enzymatically active proteasomes for continued survival| journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 98 | issue = 2| pages = 513–518 | pmid = 11149939 | doi=10.1073/pnas.021132398 | pmc=14618|display-authors=etal| doi-access = free }}
  • {{cite journal | last1 = Garrett | first1 = I.R. | year = 2003 | title = Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro| journal = J. Clin. Invest. | volume = 111 | issue = 11| pages = 1771–1782 | pmid = 12782679 | doi=10.1172/JCI16198 | pmc=156102|display-authors=etal}}
  • {{cite journal | last1 = McNaught | first1 = K.S. | year = 2004 | title = Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease| journal = Annals of Neurology | volume = 56 | issue = 1| pages = 149–162 | pmid = 15236415 | doi=10.1002/ana.20186| s2cid = 25314945 |display-authors=etal}}

Category:Epoxides

Category:Proteasome inhibitors

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