MedKoo Biosciences/Doxorubicin hydrochloride/100280/5g

Doxorubicinisananthracyclineantibioticwithantineoplasticactivity.Doxorubicin,isolatedfromthebacteriumStreptomycespeucetiusvar.caesius,isthehydroxylatedcongenerofdaunorubicin.DoxorubicinintercalatesbetweenbasepairsintheDNAhelix,therebypreventingDNAreplicationandultimatelyinhibitingproteinsynthesis.Additionally,doxorubicininhibitstopoisomeraseIIwhichresultsinanincreasedandstabilizedcleavableenzyme-DNAlinkedcomplexduringDNAreplicationandsubsequentlypreventstheligationofthenucleotidestrandafterdouble-strandbreakage.Doxorubicinalsoformsoxygenfreeradicalsresultingincytotoxicitysecondarytolipidperoxidationofcellmembranelipids;theformationofoxygenfreeradicalsalsocontributestothetoxicityoftheanthracyclineantibiotics,namelythecardiacandcutaneousvasculareffects.

MedKooCat#:100280
Name:Doxorubicinhydrochloride
CAS#:25316-40-9(HCl)
ChemicalFormula:C27H30ClNO11
ExactMass:
MolecularWeight:579.98
ElementalAnalysis:C,55.91;H,5.21;Cl,6.11;N,2.42;O,30.34

RelatedCAS#:23214-92-8(freebase) 25316-40-9(HCl)

Synonym:FI106;FI-106;FI106;ADR;Doxo;DoxHCl;Adriamycin;Adriacin;Adriblastina;Adriblastine;Adrimedac;DOXOCELL;Doxolem;Doxorubin;Farmiblastina;Rubex.

IUPAC/ChemicalName:(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dionehydrochloride

InChiKey:MWWSFMDVAYGXBV-RUELKSSGSA-N

InChiCode:InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h4-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

SMILESCode:O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)=C3C(O)=C2C(C5=C1C=CC=C5OC)=O.[H]Cl

TechnicalData

Appearance:

Redsolidpowder

Purity:

>98%(orrefertotheCertificateofAnalysis)

CertificateofAnalysis:

ViewCoA,previousbatch,Lot#TZC20130715
ViewCoA:previousbatch,Lot#EOS60126
ViewCoA:currentbatch,Lot#XPR70303

QCData:

ViewQCdata:previousbatch,Lot#TZC20130715
ViewQCdata:previousbatch,Lot#EOS60126
ViewQCdata:currentbatch,Lot#XPR70303

SafetyDataSheet(MSDS):

ViewMaterialSafetyDataSheet(MSDS)

ShippingCondition:

Shippedunderambienttemperatureasnon-hazardouschemical.ThisproductisstableenoughforafewweeksduringordinaryshippingandtimespentinCustoms.

StorageCondition:

Dry,darkandat0-4Cforshortterm(daystoweeks)or-20Cforlongterm(monthstoyears).

Solubility:

SolubleinDMSO,notinwater

ShelfLife:

>2yearsifstoredproperly

DrugFormulation:

ThisdrugmaybeformulatedinDMSO

StockSolutionStorage:

0-4Cforshortterm(daystoweeks),or-20Cforlongterm(months).

HarmonizedSystemCode:

293490

AdditionalInformation

References

1:ZhongYJ,ShaoLH,LiY.CathepsinB-cleavabledoxorubicinprodrugsfortargetedcancertherapy(Review).IntJOncol.2013Feb;42(2):373-83.doi:10.3892/ijo.2012.1754.Epub2012Dec28.Review.PubMedPMID:23291656;PubMedCentralPMCID:PMC3583876.

2:XiL,ZhuSG,DasA,ChenQ,DurrantD,HobbsDC,LesnefskyEJ,KukrejaRC.Dietaryinorganicnitratealleviatesdoxorubicincardiotoxicity:mechanismsandimplications.NitricOxide.2012May15;26(4):274-84.doi:10.1016/j.niox.2012.03.006.Epub2012Apr5.Review.PubMedPMID:22484629;PubMedCentralPMCID:PMC3360792.

3:OctaviaY,TocchettiCG,GabrielsonKL,JanssensS,CrijnsHJ,MoensAL.Doxorubicin-inducedcardiomyopathy:frommolecularmechanismstotherapeuticstrategies.JMolCellCardiol.2012Jun;52(6):1213-25.doi:10.1016/j.yjmcc.2012.03.006.Epub2012Mar21.Review.PubMedPMID:22465037.

4:PradosJ,MelguizoC,OrtizR,VÃ©lezC,AlvarezPJ,AriasJL,RuÃzMA,GallardoV,AranegaA.Doxorubicin-loadednanoparticles:newadvancesinbreastcancertherapy.AnticancerAgentsMedChem.2012Nov;12(9):1058-70.Review.PubMedPMID:22339066.

5:AiroldiM,AmadoriD,BarniS,CinieriS,DePlacidoS,DiLeoA,GennariA,IacobelliS,IontaMT,LorussoV,LotrionteM,MarchettiP,MattioliR,MinottiG,PronzatoP,RostiG,TondiniCA,VeronesiA.Clinicalactivityandcardiactolerabilityofnon-pegylatedliposomaldoxorubicininbreastcancer:asyntheticreview.Tumori.2011Nov-Dec;97(6):690-2.doi:10.1700/1018.11082.Review.PubMedPMID:22322832.

6:KhasrawM,BellR,DangC.Epirubicin:isitlikedoxorubicininbreastcancer?Aclinicalreview.Breast.2012Apr;21(2):142-9.doi:10.1016/j.breast.2011.12.012.Epub2012Jan17.Review.PubMedPMID:22260846.

7:RakowskiJA,AhmadS,HollowayRW.Useofpegylatedliposomaldoxorubicininthemanagementofplatinum-sensitiverecurrentovariancancer:currentconcepts.ExpertRevAnticancerTher.2012Jan;12(1):31-40.doi:10.1586/era.11.187.Review.PubMedPMID:22149430.

8:DugganST,KeatingGM.Pegylatedliposomaldoxorubicin:areviewofitsuseinmetastaticbreastcancer,ovariancancer,multiplemyelomaandAIDS-relatedKaposi'ssarcoma.Drugs.2011Dec24;71(18):2531-58.doi:10.2165/11207510-000000000-00000.Review.PubMedPMID:22141391.

9:MengL,ZhangX,LuQ,FeiZ,DysonPJ.Singlewalledcarbonnanotubesasdrugdeliveryvehicles:targetingdoxorubicintotumors.Biomaterials.2012Feb;33(6):1689-98.doi:10.1016/j.biomaterials.2011.11.004.Epub2011Dec2.Review.PubMedPMID:22137127.

10:MaedaM,MabuchiS,MatsumotoY,HisamatsuT,OhashiH,KimuraT.Activityofpegylatedliposomaldoxorubicinforextragenitalmullerianadenosarcomawithsarcomatousovergrowth:acasereportandareviewoftheliterature.EurJGynaecolOncol.2011;32(5):542-6.Review.PubMedPMID:22053671.

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MedKoo Biosciences/Doxorubicin hydrochloride/100280/5g

TechnicalData

AdditionalInformation

References