MANNITOLUM (TF) Mannitol

MANNITOLUM(TF)Mannitol► Obtainedbyreductionofmannose► Odourless,white,crystallinepowder,sweettaste.► OleaceaeandScrophulariaceaefamilyplantscontain.EspeciallyFraxinusornus(dişbudak)...

► Manna(KudretHelvası)maincomponent► Manna+boiledEtOHextractedandthencrystallizedtoobtainMannitol

► Preparedbycatalytic(Ni)orelectrolyticeductionofGl.andMannoz,SORBITOL+MANNITOLmixtureobtained

► Filtered,subjectedtoionexchangechromatographyandcrystallizedasmannitol

Doç.Dr.ÖzlemBahadırAcıkara

► Solubleinwaterandboilenethylalcohol► Mannitolisusedforkidneyfunctiontests► %25solutionisgivenandtheconcentrationismeasuredinbloodandurine.Itundergoesglomerularfiltrationandpracticallynotubularresorbtion

► %2.5solutionisusedforsurgeryinurology► Identificationofsomemicroorganismsinbacteriology

► Laxativeinchildren


► Sweetenerfordiabeticpatients► %5-25solutionsdiuretic(50-100g/day)► “MANNİTOLIINJECTIO”isrecordedinTurkishPharmacopoeiaasregulatorofbloodPH

► %20MANNITOL1g/KGdosageisusedinbraineudema


MANNITOLUM(TF)MANNITOL

CH2OH

CH2OH


Mannitolhexanitrate

► Mannitol+H2SO4+HNO3isusedforpreparation

► Vasodilator► Usedagainstangina

CH2ONO2O2NOO2NO

ONO2ONO2

CH2ONO2Doç.Dr.ÖzlemBahadırAcıkara

Galactose

► Itisnotfoundinnatureasfreeform► Hemisellulose,gumandmusilagescontain► Lactoseandpolysaccharidesalsocontain► Sweettasteislowerthanglucose.► Spesificrotationis+800► Lactose+%2H2SO4hydrolisationresultedin......Galactose


► Clinicallyusedforliverfunctiontests► Healthyliverconvertedgalactosetoglicogen,howeverifthefunctionsofliverarelostgalactosecanbedetectedinurine


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


► Commoninanimaltissue.► Indicationssuchas;loseofweight,alopeciaareoccuredintheabsenceofmesoinositol

► Mesoinositolplayanimportantroleinfatmetabolism.Protectliveragainstfattyliversyndrome

► Usedasatonicagainstarteriosclerosis► Mesoinositolhexanicotinate....Usedagainstenvironmental,cerebralanddiabeticcirculatoryproblems


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


► Gezengevi(Ş.urfa,Mardin,Siirt,Bitlis,Diyarbakır)occursinQuercuslibanileaves

► Yellow-brown,sticky,sweettaste► %40sucrose,► %12fructose,► %5glucose,melesitose► DoesnotcontainMANNITOL


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


► L-Rhamnose:► Aldopentose,► Methylpentose(5O,6Catoms)► 6-desoxyhexose► Aconstituentofheterogenouspolysaccharidesandglycosides

► Usedinbacteriologyforidentificationofsomemicroorganisms

► 2-desoxyoses:► Thesesugarsareoftenmetylatedat2thand6thpositions,theycontainmethylsubstituentinsteadofhydroxylgroup.

► Specifictocardiacglycosides► D-digitoxose,► L-oleandrose,D-cymarose


► D-ribose:► Pentoseasaconstituentofnucleotide.► Identificationofsomemicoorganismsinbacteriology.


Tetroses

► ErythroseanderythritoltetranitrateisimportantinPharmacy

ErythritolTetranitrate:Erythrose.....red....Erythritol+H2SO4+HNO3...ErythritolTetranitrate-Vasodilator,usedinangina-Effectivemorelongertimethanothernitratederivatives

-Inındustryforresinandplasticpreparation


Erythritoltetranitrate

CH2ONO2ONO2ONO2

CH2ONO2Doç.Dr.ÖzlemBahadırAcıkara

Trioses

► 3Cand3Oatoms► GLYCEROLUM(TF)GLİSEROL

► Propane-1,2,3-triol► Doesnotfoundinfreeforminnature,► Itisaconstituentoflipids► Atleastcontain%97propanetriol► “GlycerolumConcentratum”isalsorecordedinsomepharmacopoeiacontain%98propanetriol


Productionofglycerol

► 1)Soapindustry,saponifiedoflipids► Lipid+KOHsaponification....Glycerolsoapsolution+salt(saturatedsolution)........Upperphasesoap

► Lowerphase…….Glycerol+salt► Lowerphaseconcentrated.....saltcollapsed…Filteredandconcentrated...........glycerolisobtained,boiledwithacidandwashed,decolorizedandthencleanedafterconcentrated


2.Fermentation► Producingethylalcoholsulphideionsareaddedandglyceroloccursasthemaincomponent.Glycerolisobtainedbyextractedwithalcohol/CCl4

► Yield%15


► Identification:► Glycerol+KHSO4RheatingAcrolein+2H2O(acroleinhasspecificodour)► Usage:► Solventinpharmaceuticaltechnology► Suppositoryforitspurgativeactivity► Solventandhumectantineardrops► Emollientagainstforskinandmucoseirritation

► Demulcentactivityagainstpharynxirritationonmucousmebranes


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


Glycerol,GlycerilguaiacolateTrinitroglycerin

CH2OHCHOHCH2OH

CH2CHCH2

O NO2O NO2O NO2

OCH2OCH3

CHOH

CH2OH


Oligosaccharides► Hydrolysablebyacidsorenzymestoyieldfrom2-10moleculesofmonosaccharides

► Theyaresubdividedonthebasisofthenumberofsugarmoleculesintodi-,tri-,ortetrasaccharides…

► Polysaccharidescontainmorethan10monosaccharides

► Homogenousoligosaccharides/polysaccharidescontainsamemonosaccharides

► Heterogenousoligosaccharides/polysaccharides► containdifferentmonosaccharides


► 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)


H

O

CH2OH

O

CH2OH

HO1 1

1-1 BAĞI NONREDÜKTÖR

Non-reducingsugar


Reducingsugars

H

O

CH2OH

O

OHH

CH2OH

O

1

4

OHH

CH2OH

O

1H

O

CH2OH

O


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)


Gentianose

OCH2OH

OO

CH2

O

1

6

beta-gl

O

CH2OH

CH2OH

alfa-gl

1

fr.

2

GENSİYANOZ(NONREDÜKTÖR)


Raffinose

OCH2OH

OO

CH2

O

1

6

alfa-gal.

O

CH2OH

CH2OH

alfa-gl

1

beta-fr.

2

RAFİNOZ(NONREDÜKTÖR)


Melesitose

OCH2OH

O

OCH2OH

1

alfa-gl.

O

CH2OH

CH2OH

O

beta-fr.

alfa-gl.

23

1MELEZİTOZ


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)


ProductionofSucrosefromsugarcane

► Plantiscrushed► Subjectedtoironcylindertoyieldjuice► Sugarcanejuice+limewaterboiled(topreventinversionofthesucroseandcoagulationoftheproteins)

► Foamoccursontheupperofthesolution► CO2passedintothesolutiontoprecipitatetheexcesslime► Filtered...decoloredusingSO2► Concentratedundervacuum...Sucroseobtainedincrystallin

► Residueisknownasmolasse(MELAS)isusedtoobtainethylalcoholandasforage


Productionfromsugarbeet► Noduleshapedradixarewashed► Cutintoslices► Mixedwithhotwater(Diffusionofthewaterintotheslicesshouldbeproved)

► Crudesugarjuiceobtainedandcleaned► Mollaseobtainedfromsugarbeetcontain“BETAINE”lipotropicagentusedintreatment

► Bothplantsresultedin%15-20sucroseyield


Invertsugar

► Hydrolysedproductsofsucrose► Equalmoleculeofglucoseandfructose► Sucroserotatetheplaneofthepolarizedlighttotherightafterhydrolizationrotatetotheleft,


► Watersolutionofsucrose+Dil.NaOH+CuSO4....Bluecolour.....doesnotchangedwhenboiled(FehlingTest)Hotwatersolution+DilutedHClandthenNaOHaddition....orangecollapseoccurs.

► Thisreactionsignsucrosedoesnotcontaininvertsugar

► Sucroseisusedinpharmaceuticalpreparations,syruppreparationsandtabletmanufacture(tomaskpoortaste)

► Asanutrientanddemulcent► Bacteriostaticandprotective► Preventoxidationofsomeproducts


SACCHARUM(TF),SAKAROZ(ŞEKER),SUCROSUM,SUCROSE

OCH2OH

OH

OH

OH

O

O

CH2OHOH

OH

CH2OH


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


► Two form occur; α and βlactose► βlactosecanbesolubleeasilyinwaterthanotherform

► Usedinpharmacy► %10lactosesolutionisdiuretic► Higherconcentrationsarelaxative► Lactaseenzymedefficiencyleadstothelactoseintolerance

► Asnutrientininfantsfoodsinceitislesssweetthansucroseandmoreeasilydigested

► Alsousedasinertdiluentforotherdrugs


SACCHARUMLACTIS(TF),LAKTOZ,Lactose

OCH2OH

OCH2OH

O

1 4

beta-gal.beta-gl.


Lactulose

► 1molgal.and1molfr.1-4glycosidicbond► Laxative► Doesnotabsorbedfromgastrointestinaltract► Semi-syntheticdisaccharide► PreventNH3producingmicroorganisms► Treatmentofhepaticencephalopathy


Lactulose

OCH2OH

O

1

beta-gal.

O OH

CH2OH

CH2OH

4

beta-fr.


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)


Heterogenouspolysaccharides

► Heteropolysaccharides► Differentmonosaccharides► Uronicacidderivatives► Acidicpolysaccharides► Neutralpolysaccharides► Gums,mucilages,pectinsandhemicellulose


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.


Documents

MANNITOLUM (TF) Mannitol