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{{chembox |
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| verifiedrevid = 384239649 |
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|Reference=<ref> at ]</ref> |
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| Reference = <ref> at ]</ref> |
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|ImageFile=Ubenimex.png |
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| ImageFile = Ubenimex2DCSD.svg |
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|ImageSize=200px |
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| ImageSize = 250px |
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|IUPACName= (2''S'')-2-<nowiki>amino]-4-methylpentanoic acid |
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| ImageFile2 = Ubenimex3DanJ.gif |
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|OtherNames=Bestatin; ''N''--<small>L</small>-leucine |
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| ImageSize2 = 250px |
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| IUPACName = ''N''--<small>L</small>-leucine |
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| SystematicName = (2''S'')-2--4-methylpentanoic acid |
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| OtherNames = Bestatin; ''N''--<small>L</small>-leucine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo= 58970-76-6 |
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| CASNo1 = 65391-42-6 |
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| CASOther = <br>65391-42-6 (]) |
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| CASNo1_Comment = (]) |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem=72172 |
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| CASNo = 58970-76-6 |
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| SMILES=CC(C)C(C(=O)O)NC(=O)((CC1=CC=CC=C1)N)O |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 29292 |
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| DrugBank = DB03424 |
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| KEGG = D00087 |
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| EC_number = 261-529-2 |
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| PubChem = 72172 |
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| SMILES = CC(C)C(C(=O)O)NC(=O)((CC1=CC=CC=C1)N)O |
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| ChemSpiderID = 65145 |
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| StdInChI = 1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1 |
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| StdInChIKey = VGGGPCQERPFHOB-RDBSUJKOSA-N |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = I0J33N5627 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=16|H=24|N=2|O=4 |
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| C =16|H=24|N=2|O=4 |
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| Appearance= |
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| Appearance = |
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| Density= |
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| Density = |
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| MeltingPtC = 245 |
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| MeltingPt=245 °C (dec.) |
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| MeltingPt_notes = (decomposes) |
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| BoilingPt= |
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| BoilingPt = |
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| Solubility= |
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| Solubility = |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards = |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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| Autoignition= |
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| GHS_ref=<ref>{{cite web |title=Ubenimex |url=https://pubchem.ncbi.nlm.nih.gov/compound/72172#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}</ref> |
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| SPhrases = {{S22}} {{S24/25}} |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405}} |
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'''Ubenimex''' (]), also known as '''bestatin''', is a competitive ]. It is an ] of aminopeptidase B<ref>{{cite journal | year = 1976 | issue = 29 | pages = 97–99 | title = Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes.| author = Umezawa,H., Aoyagi,T., Suda,H., Hamada,M. & Takeuchi,T.}}</ref>, ] <ref>{{cite journal | year = 1994 | issue = 48 | pages = 131–137 | title = Modulation of pulmonary leukotriene formation and perfusion pressure by bestatin, an inhibitor of leukotriene A4 hydrolase.| author = Muskardin,D.T., Voelkel,N.F. & Fitzpatrick,F.A.}}</ref>, ].<ref>{{cite journal | year = 1999 | issue = 5 | pages = 729–734 | title = Induction of apoptosis by bestatin (ubenimex) in human leukemic cell lines | author = K Sekine, H Fujii and F Abe | volume = 13}}</ref> It is being studied for use in the treatment of ].<ref>{{Cite journal | pmid = 12938265 | year = 2003 | last1 = Hirayama | first1 = Y | last2 = Sakamaki | first2 = S | last3 = Takayanagi | first3 = N | last4 = Tsuji | first4 = Y | last5 = Sagawa | first5 = T | last6 = Chiba | first6 = H | last7 = Matsunaga | first7 = T | last8 = Niitsu | first8 = Y | title = Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival | volume = 30 | issue = 8 | pages = 1113–8 | journal = Gan to kagaku ryoho. Cancer & chemotherapy}}</ref> |
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'''Ubenimex''' (]), also known more commonly as '''bestatin''', is a competitive, reversible ]. It is an ] of ] (aminopeptidase B),<ref>{{cite journal | year = 1976 | issue = 29 | pages = 97–99 | title = Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes.| author = Umezawa, H.| author2 = Aoyagi, T.| author3 = Suda, H.| author4 = Hamada, M.| author5 = Takeuchi, T.| journal = The Journal of Antibiotics | volume = 29 | doi = 10.7164/antibiotics.29.97 | pmid = 931798 | doi-access = free }}</ref> ] (a ] that displays both ] and ] activities),<ref>{{cite journal | year = 1994 | issue = 48 | pages = 131–137 | title = Modulation of pulmonary leukotriene formation and perfusion pressure by Bestatin, an inhibitor of leukotriene A4 hydrolase.| author = Muskardin, D.T.| author2 = Voelkel, N.F.| author3 = Fitzpatrick, F.A.| journal = Biochemical Pharmacology | volume = 48 | doi = 10.1016/0006-2952(94)90232-1 | pmid = 8043014 }}</ref> ] (aminopeptidase M/N),<ref>{{cite journal | year = 1999 | issue = 5 | pages = 729–734 | title = Induction of apoptosis by Bestatin (ubenimex) in human leukemic cell lines |author1=K Sekine |author2=H Fujii |author3=F Abe | journal = Leukemia | volume = 13 | doi=10.1038/sj.leu.2401388| pmid = 10374877 | doi-access = free }}</ref> ] (oxytocinase/vasopressinase),<ref name="pmid10985965">{{cite journal | vauthors = Nakanishi Y, Nomura S, Okada M, Ito T, Katsumata Y, Kikkawa F, Hattori A, Tsujimoto M, Mizutani S | title = Immunoaffinity purification and characterization of native placental leucine aminopeptidase/oxytocinase from human placenta | journal = Placenta | volume = 21 | issue = 7 | pages = 628–34 | year = 2000 | pmid = 10985965 | doi = 10.1053/plac.2000.0564 }}</ref><ref name="pmid8801531">{{cite journal | vauthors = Naruki M, Mizutani S, Goto K, Tsujimoto M, Nakazato H, Itakura A, Mizuno K, Kurauchi O, Kikkawa F, Tomoda Y | title = Oxytocin is hydrolyzed by an enzyme in human placenta that is identical to the oxytocinase of pregnancy serum | journal = Peptides | volume = 17 | issue = 2 | pages = 257–61 | year = 1996 | pmid = 8801531 | doi = 10.1016/0196-9781(95)02124-8| s2cid = 28486489 }}</ref> and ] (leukotriene D<sub>4</sub> hydrolase). It is being studied for use in the treatment of ]<ref>{{Cite journal | pmid = 12938265 | year = 2003 | last1 = Hirayama | first1 = Y | last2 = Sakamaki | first2 = S | last3 = Takayanagi | first3 = N | last4 = Tsuji | first4 = Y | last5 = Sagawa | first5 = T | last6 = Chiba | first6 = H | last7 = Matsunaga | first7 = T | last8 = Niitsu | first8 = Y | title = Chemotherapy with ubenimex corresponding to patient age and organ disorder for 18 cases of acute myelogeneous leukemia in elderly patients--effects, complications and long-term survival | volume = 30 | issue = 8 | pages = 1113–8 | journal = Gan to Kagaku Ryoho. Cancer & Chemotherapy}}</ref> and ].<ref>{{Cite journal | pmid = 28490670 | year = 2017 | last1 = Tian | first1 = W | last2 = Rockson | first2 = S | last3 = Jiang | first3 = X | last4 = Kim | first4 = J | last5 = Begaye | first5 = A | last6 = Shuffle | first6 = EM | last7 = Tu | first7 = AB | last8 = Cribb | first8 = M | last9 = Nepiyushchikh | first9 = Z | last10 = Feroze | first10 = AH | last11 = Zamanian | first11 = RT | last12 = Dhillon | first12 = RT | last13 = Voelkel | first13 = NF | last14 = Peters-Golden | first14 = M | last15 = Kitajewski | first15 = J | last16 = Dixon | first16 = JB | last17 = Nicolls | first17 = MR | title = Leukotriene B4 antagonism ameliorates experimental lymphedema | volume = 9 | issue = 389 | pages = eaal3920 | journal = Science Translational Medicine | doi=10.1126/scitranslmed.aal3920| doi-access = free }}</ref> |
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It is derived from '']''.<ref>{{cite journal|last=Bauvois|first=B|author2=Dauzonne, D |title=Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: Chemistry, biological evaluations, and therapeutic prospects|journal=Medicinal Research Reviews|volume=26|issue=1|pages=88–130|doi=10.1002/med.20044|pmid=16216010|date=January 2006|pmc=7168514}}</ref> Ubenimex has been found to inhibit the enzymatic degradation of ], ], ]s, and various other ]s and compounds.{{Citation needed|date=October 2015}} |
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==See also== |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist|2}} |
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==External links== |
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* The ] online database for peptidases and their inhibitors: |
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{{Leukotrienergics}} |
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{{Opioidergics}} |
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==External Links== |
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{{pharma-stub}} |
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* The ] online database for peptidases and their inhibitors: |
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