MANNITOLUM(TF)Mannitol► Obtainedbyreductionofmannose► Odourless,white,crystallinepowder,sweettaste.► OleaceaeandScrophulariaceaefamilyplantscontain.EspeciallyFraxinusornus(dişbudak)...
► Manna(KudretHelvası)maincomponent► Manna+boiledEtOHextractedandthencrystallizedtoobtainMannitol
► Preparedbycatalytic(Ni)orelectrolyticeductionofGl.andMannoz,SORBITOL+MANNITOLmixtureobtained
► Filtered,subjectedtoionexchangechromatographyandcrystallizedasmannitol
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► Solubleinwaterandboilenethylalcohol► Mannitolisusedforkidneyfunctiontests► %25solutionisgivenandtheconcentrationismeasuredinbloodandurine.Itundergoesglomerularfiltrationandpracticallynotubularresorbtion
► %2.5solutionisusedforsurgeryinurology► Identificationofsomemicroorganismsinbacteriology
► Laxativeinchildren
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► Sweetenerfordiabeticpatients► %5-25solutionsdiuretic(50-100g/day)► “MANNİTOLIINJECTIO”isrecordedinTurkishPharmacopoeiaasregulatorofbloodPH
► %20MANNITOL1g/KGdosageisusedinbraineudema
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MANNITOLUM(TF)MANNITOL
CH2OH
CH2OH
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Mannitolhexanitrate
► Mannitol+H2SO4+HNO3isusedforpreparation
► Vasodilator► Usedagainstangina
CH2ONO2O2NOO2NO
ONO2ONO2
CH2ONO2Doç.Dr.ÖzlemBahadırAcıkara
Galactose
► Itisnotfoundinnatureasfreeform► Hemisellulose,gumandmusilagescontain► Lactoseandpolysaccharidesalsocontain► Sweettasteislowerthanglucose.► Spesificrotationis+800► Lactose+%2H2SO4hydrolisationresultedin......Galactose
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► Clinicallyusedforliverfunctiontests► Healthyliverconvertedgalactosetoglicogen,howeverifthefunctionsofliverarelostgalactosecanbedetectedinurine
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Galactose
OCH2OHOHOH
OH
CHO
CH2OHDoç.Dr.ÖzlemBahadırAcıkara
Mesoinositol
► Hexitolincyclicstructure► 8cis-transisomer,1opticalisomer► Mesoinositolinplantsdoesnothaveopticalisomer► Mesoinositol+H3PO4….phyticacid(Mesoinositolhexaphosphate)► Phytin,acalciummagnesiumsaltofphyticacidthatoccursinplantsasthemainphosporusstoragereserveespeciallyinseedsortubersandisusedasasourceofinositol.► Usedasanabolic.Doç.Dr.ÖzlemBahadırAcıkara
Mesoinositol
OHOHOH
OH
OHOH
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► Commoninanimaltissue.► Indicationssuchas;loseofweight,alopeciaareoccuredintheabsenceofmesoinositol
► Mesoinositolplayanimportantroleinfatmetabolism.Protectliveragainstfattyliversyndrome
► Usedasatonicagainstarteriosclerosis► Mesoinositolhexanicotinate....Usedagainstenvironmental,cerebralanddiabeticcirculatoryproblems
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Manna(TK)► Sourceofmannitol► Differenttypesofmannaareoccurs:► Briansonmanna,occursnaturally► Effectofinsects(EucalyptusandTamarix)► Woundingofplants(Fraxinus)► Lecanoraesculentalichenknownasmanna► LecanoraesculentaandknownasMANNAOFJEW(İbraniMannası)
► ► Insectspreparedaproductwithcompoundsfromplants(Trehalamanna)
► FraxinusornusL.(Oleaceae)woundingofbodyresultedinmannaoccurence
► 20mhigh,5-9leaflets,whiteflowersDoç.Dr.ÖzlemBahadırAcıkara
► WestandNorthwestAnatolia► MannaisnotobtainedinAnatolia► Siciliaisthemaincountryformanna► OutersidesoftheMannaisstrawyellow,insideiswhitecolour,honeylikesmellsandsweettaste
► %30-80ofmannitol,gl.,fr.,resin► Inchildren5-30g/daydosagelaxative► F.excelsiorL.,40m.high,7-13leaflets► ItgrowsatmountainsinNorthAnatolia► %2infusionofleavesareusedasdiuretic,galactagogueandlaxative
► Cortexoftheplantisusedasantipyretic,constipatingandtonicDoç.Dr.ÖzlemBahadırAcıkara
► Mannitol,Sorbitol,Gl.,Trehalose(gl+gl),melitose(fr+gl+gal),melesitose(gl+fr+gl)
► MANNADEPURATAaproductobtainedfromwoundsandhardeningonthebody
► %40-60D-mannitol,► mannatriose(gl+gal+gal)ve► mannatetrose(mannotriose+fr)► Musilagevefraxinoside(Coumarin)► Laxativeandpurgative
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► Gezengevi(Ş.urfa,Mardin,Siirt,Bitlis,Diyarbakır)occursinQuercuslibanileaves
► Yellow-brown,sticky,sweettaste► %40sucrose,► %12fructose,► %5glucose,melesitose► DoesnotcontainMANNITOL
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Pentoses► 5oxygenand5Catoms► D-xyloseandL-arabinose► D-Glucose.........D-glucuronicacid.........D-xylose
► D-galactose......D-galacturonikacid....L-arabinose
► D-xyloseandL-arabinose► Commonconstituentsofcomplexpolysaccharides,hemicelluloses(xyloglucans,xylans,glucuronoxylans,arabinoxylans,glucuronoarabinoxylans),pepticpolysaccharides,mucilagesandgums
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► L-Rhamnose:► Aldopentose,► Methylpentose(5O,6Catoms)► 6-desoxyhexose► Aconstituentofheterogenouspolysaccharidesandglycosides
► Usedinbacteriologyforidentificationofsomemicroorganisms
► 2-desoxyoses:► Thesesugarsareoftenmetylatedat2thand6thpositions,theycontainmethylsubstituentinsteadofhydroxylgroup.
► Specifictocardiacglycosides► D-digitoxose,► L-oleandrose,D-cymarose
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► D-ribose:► Pentoseasaconstituentofnucleotide.► Identificationofsomemicoorganismsinbacteriology.
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Tetroses
► ErythroseanderythritoltetranitrateisimportantinPharmacy
ErythritolTetranitrate:Erythrose.....red....Erythritol+H2SO4+HNO3...ErythritolTetranitrate-Vasodilator,usedinangina-Effectivemorelongertimethanothernitratederivatives
-Inındustryforresinandplasticpreparation
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Erythritoltetranitrate
CH2ONO2ONO2ONO2
CH2ONO2Doç.Dr.ÖzlemBahadırAcıkara
Trioses
► 3Cand3Oatoms► GLYCEROLUM(TF)GLİSEROL
► Propane-1,2,3-triol► Doesnotfoundinfreeforminnature,► Itisaconstituentoflipids► Atleastcontain%97propanetriol► “GlycerolumConcentratum”isalsorecordedinsomepharmacopoeiacontain%98propanetriol
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Productionofglycerol
► 1)Soapindustry,saponifiedoflipids► Lipid+KOHsaponification....Glycerolsoapsolution+salt(saturatedsolution)........Upperphasesoap
► Lowerphase…….Glycerol+salt► Lowerphaseconcentrated.....saltcollapsed…Filteredandconcentrated...........glycerolisobtained,boiledwithacidandwashed,decolorizedandthencleanedafterconcentrated
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2.Fermentation► Producingethylalcoholsulphideionsareaddedandglyceroloccursasthemaincomponent.Glycerolisobtainedbyextractedwithalcohol/CCl4
► Yield%15
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► Identification:► Glycerol+KHSO4RheatingAcrolein+2H2O(acroleinhasspecificodour)► Usage:► Solventinpharmaceuticaltechnology► Suppositoryforitspurgativeactivity► Solventandhumectantineardrops► Emollientagainstforskinandmucoseirritation
► Demulcentactivityagainstpharynxirritationonmucousmebranes
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GLYCERIYLISTRINITRATIS,TRİNİTRİN,TRİNİTROGLİSERİN
Nıtroglyceryn,trinitrine► ConcentratedHNO3+ConcentratedH2SO4...+incoldtogetherwithglycerol
TRINITRINEisobtained► Explosice,colourless/paleyellowcolourandvolatile
► Incolditisdurablehoweverinhotcanbehydrolisedeasily
► “GlycerylisTrinitratisCompressi”assublingualtabletsusedforcoronaryvasodilator
► Dosage0.3-1.0mg► Mixedwithlactose► Prophylacticandtreateningactivityinangina► Dizziness,tachycardia,headache,aresideeffects Doç.Dr.ÖzlemBahadırAcıkara
GlycerylGuaiacolate► Guaiacolglycerylether
► Usage;Temporaryreliefofcoughassociatedwithrespiratorytractinfectionsandrelatedconditions,suchassinusitis,pharyngitis,bronchitis,andasthma,whentheseconditionsarecomplicatedbytenaciousmucusormucusplugsandcongestion;effectiveforproductiveaswellasnonproductivecough,particularly,dry,nonproductivecoughthattendstoinjuremucousmembranesoftheairpassages;helpsloosenphlegmandthinbronchialsecretionsinpatientswithstablechronicbronchitis.
► GLYCERYLTRIACETATE,TRIACETIN► Glycerol+CH3COOH....esther► SolventinPharmaceuticaltechnology► Colourless,hottaste,heavythanwaterandgreasy► Mixedwithwater,alcohol,etherandCHCl3
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Glycerol,GlycerilguaiacolateTrinitroglycerin
CH2OHCHOHCH2OH
CH2CHCH2
O NO2O NO2O NO2
OCH2OCH3
CHOH
CH2OH
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Oligosaccharides► Hydrolysablebyacidsorenzymestoyieldfrom2-10moleculesofmonosaccharides
► Theyaresubdividedonthebasisofthenumberofsugarmoleculesintodi-,tri-,ortetrasaccharides…
► Polysaccharidescontainmorethan10monosaccharides
► Homogenousoligosaccharides/polysaccharidescontainsamemonosaccharides
► Heterogenousoligosaccharides/polysaccharides► containdifferentmonosaccharides
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► Monosaccharideunitsarelinkedthroughglycosidiclinkages
► Differentpositionscanbeplacedsuchas;1-1,1-4,1-6,1-2
► 1-4and1-6glycosidiclinkage,reducingsugars► Maltose(1-4)(gl-gl)(Homogenousdisaccharide)► Gentiobiose(1-6)(gl-gl)(Homogenousdisaccharide)► Primeverose(6-1)(gl-xyl)(Heterogenousdisaccharide)
► Lactose(1-4)(gl-gal)(Heterogenousdisaccharide)
► 1-2linkagesuchassucrosenon-reducingsugars► Sucrose(1-2)(gl-fruc)(Heterogenousdisaccharide)
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H
O
CH2OH
O
CH2OH
HO1 1
1-1 BAĞI NONREDÜKTÖR
Non-reducingsugar
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Reducingsugars
H
O
CH2OH
O
OHH
CH2OH
O
1
4
OHH
CH2OH
O
1H
O
CH2OH
O
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DisaccharidesO
CH2OH
O
CH2OH
CH2OH
O1 2
alfa-gl alfa-gl
SAKAROZ (NONREDÜKTÖR)
OCH2OH
O
OCH2OH
1 4
alfa-gl alfa-gl
MALTOZ(REDÜKTÖR)
OCH2OH
OO
CH2
1
6
beta-gl beta-gl
GENSİYOBİOZ(REDÜKTÖR)
Sucrose
Maltose GentiobioseDoç.Dr.ÖzlemBahadırAcıkara
Trisaccharides
► Gentianose(gl-gl-fr)(R.Gentianae)► Raffinose(gal-gl-fr)(Gossypiumseed)► Melezitose(gl-fr-gl)(Manna)
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Gentianose
OCH2OH
OO
CH2
O
1
6
beta-gl
O
CH2OH
CH2OH
alfa-gl
1
fr.
2
GENSİYANOZ(NONREDÜKTÖR)
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Raffinose
OCH2OH
OO
CH2
O
1
6
alfa-gal.
O
CH2OH
CH2OH
alfa-gl
1
beta-fr.
2
RAFİNOZ(NONREDÜKTÖR)
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Melesitose
OCH2OH
O
OCH2OH
1
alfa-gl.
O
CH2OH
CH2OH
O
beta-fr.
alfa-gl.
23
1MELEZİTOZ
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SACCHARUM(TF),SAKAROZ(ŞEKER),SUCROSUM,SUCROSE
► α-D- glucopyranose+ β-D-fructofuranoseα 1-2glycosidicbond
► Mostwidelyoccuringdisaccharide► Nonreducingsugarandhydrolysedbyinvertaseenzymetoglucoseandfructose
► ObtainedinIndustry;► 1)Saccharumofficinarum(Sugarcane,şekerkamışı(Graminae)(Cuba,Puertorico,ThePhilippines,İndia,Indonesia)
► 2)Betavulgaris(Şugarbeet,Şekerpancarı)(Chenopodiaceae)(Germany,Austria,Russia,FranseandUSA)
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ProductionofSucrosefromsugarcane
► Plantiscrushed► Subjectedtoironcylindertoyieldjuice► Sugarcanejuice+limewaterboiled(topreventinversionofthesucroseandcoagulationoftheproteins)
► Foamoccursontheupperofthesolution► CO2passedintothesolutiontoprecipitatetheexcesslime► Filtered...decoloredusingSO2► Concentratedundervacuum...Sucroseobtainedincrystallin
► Residueisknownasmolasse(MELAS)isusedtoobtainethylalcoholandasforage
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Productionfromsugarbeet► Noduleshapedradixarewashed► Cutintoslices► Mixedwithhotwater(Diffusionofthewaterintotheslicesshouldbeproved)
► Crudesugarjuiceobtainedandcleaned► Mollaseobtainedfromsugarbeetcontain“BETAINE”lipotropicagentusedintreatment
► Bothplantsresultedin%15-20sucroseyield
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Invertsugar
► Hydrolysedproductsofsucrose► Equalmoleculeofglucoseandfructose► Sucroserotatetheplaneofthepolarizedlighttotherightafterhydrolizationrotatetotheleft,
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► Watersolutionofsucrose+Dil.NaOH+CuSO4....Bluecolour.....doesnotchangedwhenboiled(FehlingTest)Hotwatersolution+DilutedHClandthenNaOHaddition....orangecollapseoccurs.
► Thisreactionsignsucrosedoesnotcontaininvertsugar
► Sucroseisusedinpharmaceuticalpreparations,syruppreparationsandtabletmanufacture(tomaskpoortaste)
► Asanutrientanddemulcent► Bacteriostaticandprotective► Preventoxidationofsomeproducts
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SACCHARUM(TF),SAKAROZ(ŞEKER),SUCROSUM,SUCROSE
OCH2OH
OH
OH
OH
O
O
CH2OHOH
OH
CH2OH
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SACCHARUMLACTIS(TF),LAKTOZ,Lactose
► Itistheprincipalsugarofmammalianmilk,► Notpresentinhigherplants► β-galactopyranose+β-D-glucopyranose....(1-4)
disaccharide► Hydrolysedbyβ-galactosidases► Crystalline,odourless,lightsweettaste► Obtainedfromremainwaterpartofproductionofthe
cheesefrommilk,incrystallineform► Crsytallsareseparated► Decolouringwithactivatedcarbon► Crystallineagain
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► Two form occur; α and βlactose► βlactosecanbesolubleeasilyinwaterthanotherform
► Usedinpharmacy► %10lactosesolutionisdiuretic► Higherconcentrationsarelaxative► Lactaseenzymedefficiencyleadstothelactoseintolerance
► Asnutrientininfantsfoodsinceitislesssweetthansucroseandmoreeasilydigested
► Alsousedasinertdiluentforotherdrugs
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SACCHARUMLACTIS(TF),LAKTOZ,Lactose
OCH2OH
OCH2OH
O
1 4
beta-gal.beta-gl.
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Lactulose
► 1molgal.and1molfr.1-4glycosidicbond► Laxative► Doesnotabsorbedfromgastrointestinaltract► Semi-syntheticdisaccharide► PreventNH3producingmicroorganisms► Treatmentofhepaticencephalopathy
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Lactulose
OCH2OH
O
1
beta-gal.
O OH
CH2OH
CH2OH
4
beta-fr.
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Polysaccharides(Homogenous)Homosaccharides
► Widelyfoundinplantkingdom► Arabinose..........Arabans(gumsandmucilages)► Xylose................Xylans(Angiospermae,lignifiedtissue)
► Mannose...........Mannan(Gymnospermaelignifiedtissueandinsomealgaeassupplementmaterial)
► Fructose.............Fructosans(Supplementmaterialsuchasinulin)
► Galactose...........Galactans(Pecticsubstancesandgelose(agar))
► Glucose..............Glucans(starch,cellulose,dextran,dextrin,glycogen)
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Heterogenouspolysaccharides
► Heteropolysaccharides► Differentmonosaccharides► Uronicacidderivatives► Acidicpolysaccharides► Neutralpolysaccharides► Gums,mucilages,pectinsandhemicellulose
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Polysaccharides
► Dissolveinwaterpartially,► EthylalcoholorCa,Mg,Basaltsproduceprecipitate
► TheyareswellingandtheirswellingindexisrecordedinPharmacopoeia
► The swelling index is the volume in millilitres occupied by 1 gram of a drug, after it has swollen in an aqueous liquid for 4 h.
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