MedKoo Biosciences/Batimastat/200442/25mg

Synonym:BB94;BB-94;BB94;Batimastat.

IUPAC/ChemicalName:(2S,3R)-N-Hydroxy-N-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide.

InChiKey:XFILPEOLDIKJHX-QYZOEREBSA-N

InChiCode:InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1

SMILESCode:O=C(NO)[C@@H](CSC1=CC=CS1)[C@@H](CC(C)C)C(N[C@@H](CC2=CC=CC=C2)C(NC)=O)=O

TechnicalData

AdditionalInformation

Related:
130370-60-4(Batimastatfreebaseform)
130464-84-5(Batimastatsodiumsaltform).

Batimastatisapotent,broadspectrummatrixmetalloprotease(MMP)inhibitor(IC50valuesare3,4,4,6and20nMforMMP-1,-2,-9,-7and-3respectively).Exhibitsantiproliferative,anti-invasiveandantimetastaticactivityinhumanovariancarcinomaxenograftsinvivo.
 
Batimastat(INN/USAN,codenamedBB-94)isananticancerdrugthatbelongstothefamilyofdrugscalledangiogenesisinhibitors.Itactsasamatrixmetalloproteinaseinhibitor(MMPI)bymimickingnaturalMMPIpeptides.BatimastatwasthefirstMMPIthatwentintoclinicaltrials.FirstresultsofaPhaseItrialappearedin1994.ThedrugreachedPhaseIIIbutwasnevermarketed;mainlybecauseitcouldn'tbeadministeredorally(asopposedtothenewerandchemicallysimilarMMPImarimastat),andinjectionintotheperitoneumcausedperitonitis.(http://en.wikipedia.org/wiki/Batimastat)
 
 

References

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2:HallT,ShiehHS,DayJE,CaspersN,ChrencikJE,WilliamsJM,PeggLE,PauleyAM,MoonAF,KrahnJM,FischerDH,KieferJR,TomasselliAG,ZackMD.StructureofhumanADAM-8catalyticdomaincomplexedwithbatimastat.ActaCrystallogrSectFStructBiolCrystCommun.2012Jun1;68(Pt6):616-21.doi:10.1107/S1744309112015618.Epub2012May22.PubMedPMID:22684055;PubMedCentralPMCID:PMC3370895.

3:KumarA,BhatnagarS,KumarA.Matrixmetalloproteinaseinhibitorbatimastatalleviatespathologyandimprovesskeletalmusclefunctionindystrophin-deficientmdxmice.AmJPathol.2010Jul;177(1):248-60.doi:10.2353/ajpath.2010.091176.Epub2010May14.PubMedPMID:20472898;PubMedCentralPMCID:PMC2893668.

4:GeSL,GongWH,ZhangCX,ZhangL,HanPH,ZhangSQ,FengJB,ZhouDC.[ProtectiveroleofMMP-9inhibitorbatimastatinacutelunginjuryaftercardiopulmonarybypass].ZhonghuaWaiKeZaZhi.2010Jan1;48(1):57-61.Chinese.PubMedPMID:20302758.

5:MuchaSA,Meleń-MuchaG,GodlewskiA,StepieńH.Inhibitionofestrogen-inducedpituitarytumorgrowthandangiogenesisinFischer344ratsbythematrixmetalloproteinaseinhibitorbatimastat.VirchowsArch.2007Mar;450(3):335-41.Epub2007Jan18.PubMedPMID:17235567.

6:AraujoCM,RandoGA,MauroMF,CristóvãoSA,SanchezIS,SalmanAA,OliveiraNetoJB,MangioneJA.[Batimastat-elutingstentimplantationforthetreatmentofcoronaryarterydisease:resultsoftheBrazilianpilotstudy].ArqBrasCardiol.2005Mar;84(3):256-60.Epub2005Apr15.Portuguese.PubMedPMID:15868002.

7:vanBeusekomHM,PostMJ,WhelanDM,deSmetBJ,DunckerDJ,vanderGiessenWJ.Metalloproteinaseinhibitionbybatimastatdoesnotreduceneointimalthickeninginstentedatheroscleroticporcinefemoralarteries.CardiovascRadiatMed.2003Oct-Dec;4(4):186-91.PubMedPMID:15321056.

8:BjörnssonMJ,Havemose-PoulsenA,StoltzeK,HolmstrupP.Influenceofthematrixmetalloproteinaseinhibitorbatimastat(BB-94)onperiodontalbonedestructioninSprague-Dawleyrats.JPeriodontalRes.2004Aug;39(4):269-74.PubMedPMID:15206921.

9:RucavadoA,EscalanteT,GutiérrezJM.EffectofthemetalloproteinaseinhibitorbatimastatinthesystemictoxicityinducedbyBothropsaspersnakevenom:understandingtheroleofmetalloproteinasesinenvenomation.Toxicon.2004Mar15;43(4):417-24.PubMedPMID:15051405.

10:SantucciMB,CiaramellaA,MatteiM,SumerskaT,FrazianoM.BatimastatreducesMycobacteriumtuberculosis-inducedapoptosisinmacrophages.IntImmunopharmacol.2003Nov;3(12):1657-65.PubMedPMID:14555290.