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VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS OF PYRIDOXALAND PYRIDOXAMINE,VITAMIN B6 USES.
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VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS OF PYRIDOXALAND PYRIDOXAMINE,VITAMIN B6 USES.

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VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS ...

VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS OF PYRIDOXALAND PYRIDOXAMINE,VITAMIN B6 USES.

P.RAIVSANKAR
VIGNAN PHARMACY COLLEGE, VADLAMUDI.

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VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS OF PYRIDOXALAND PYRIDOXAMINE,VITAMIN B6 USES. VITAMIN B6 [MEDICINAL CHEMISTRY] BY P.RAVISANKAR. SOURCES,STRUCTURES OF PYRIDOXINE,PYRIDOXAL,PYRIDOXAMINE,DEFICIENCY OF VITAMIN B6,PYRIDOXINE ANTAGONISTS, METABOLISM,PHYSIOGICAL IMPORTANCE,SYNTHESIS OF PYRIDOXALAND PYRIDOXAMINE,VITAMIN B6 USES. Presentation Transcript

  • Prof. RavisankarVignan Pharmacy collegeValdlamudiGuntur Dist.Andhra PradeshIndia.banuman35@gmail.com00919059994000
  • Vitamin B 6 is a water-soluble vitamin present in three major chemicalforms:pyridoxine, pyridoxal,pyridoxamineThese three are interconvertible in their phosphorylated form.It is also called Adermin,because it is used as an antidermatitic factor(acrodynia factor )for rats.The plant sources mainly contain pyridoxal,pyridoxamine and animalsources contain Pyridoxine.Active form is pyridoxal phosphateIt is essential coenzyme for trans amination and decarboxylation ofamino acids.NCH2OHCH2OHHOH3CPYRIDOXINENCHOCH2OHHOH3C NCH2NH2CH2OHHOH3CPYRIDOXAMINEPYRIXOXALCollectively, pyridoxine, pyridoxal and pyridoxamine are known as vitamin B6.(Pyridoxol)[2-methyl-3-hydroxy-4-5di(hydroxymethyl)-Pyridine]123 4 56
  • Chick peasWholegrain breads and cereals are rich in Vitamin B6Wholegrain breads and cereals are richin Vitamin B6Sweet potatoes
  • The best source of vitamin B6 is through the foods you eat. Foods rich in vitamin B6 include:Avocado (raw),Baked potato (flesh and skin)Fortified cereals, beans, Lima beans,Peanut butter ,Poultry ,Spinach, Soybeans, Sunflowerseeds Tomato juice, WalnutsbananasbeefBrewers Yeastbrown rice huskscabbagedried fruitseggsfish, fatty, whitefishgreen leafy vegetablesmaizemeatsmilknuts, oatsorgan meats, especially pig liverpotatoespulses, such as lentilsroot vegetablessoy products, pepperswheat branwheat germwhole grain•
  • Deficiency leads toIn humans vitaminB6 deficiency leads to neurological symptoms likedepression,irritability,nervousness,mental confusion.Dermatitis in rats and other animals due to pyridoxosis.Anemiaconfusionconvulsions( due to decreased synthesis of serotonin,GABA,catacholamines)DepressionSore tongue,defective sexual behaviour,decreased heam synthesis.Since most of us easily get enough B6 in our diets, then who should take B6supplements? :Alcoholics (Alcohol also helps to deplete B6 from the body)Asthmatic children who take theophylline because it too depletes stores of B6 from thebodyElderly.General guidelines recommend keeping your B6 intake to less than 100 mgdaily. This includes B6 from both dietary sources as well as supplements.However, as we age, our need for vitamin B6 increases, and 1.9 mg is the RDAfor pregnant women, and it goes up to 2.0 mg for lactating women.
  • •pyridoxine is stable in acid solution, but unstable in neutral oralkaline solutions (destroyed by light).NNNH-NH2Hydralazine (antihypertensive)NCO NHNH2isoniazid (antitubercular)ONOH2NHcycloserine (antitubercular)CCCH3 HCOOHHSCH3 NH2penicillamine (antirheumatic; Wilsons disease)Pyridoxine antagonists.increasing renal excretion of pyridoxine; recommended intakes for pyridoxinemay be increased in patients receiving these medicationsThe taking of certain drugs (as isoniazid, hydrolazine, penicillamine) thatinactivate the vitamin.
  • Levodopa (concurrent use with pyridoxine is not recommended sincelevodopas antiparkinsonian effects are reversed by as little as 5 mg ofpyridoxine orally; this problem does not occur with the carbidopa-levodopacombination.Pyridoxine (vitamin B 6) has been found to reduce the effects of levodopawhen levodopa is taken by itself.MetabolismMetabolized in the liver and converted to 4-pyridoxic acid metabolite.EliminationExcreted mostly as 4-pyridoxic acid in the urine. The t ½ is 15 to 20 days.Parenteral use is indicated when oral therapy is not feasible.Parenteral use is indicated when oral therapy is not feasible.Vitamin B6 is usually safe, at intakes up to 200 mg per day in adults.However, vitamin B6 can cause neurological disorders, such as loss ofsensation in legs and imbalance, when taken in high doses (200 mg ormore per day) over a long period of time
  • Physiological importance:Physiologically active form of vitamin B6 is pyridoxal-5-phosphate.It acts ascoenzyme for the enzymes that are involved in the biosynthesis of niacin,coenzyme A and haemoglobin.It is also involved in reactions like transamination,amino aciddecorboxylation,desulphuration and metabolism of unsaturated fatty acids.Pyridoxal-5-phosphate also acts as coenzyme in the formation of serotoninfrom tryptophan,cystine from methionine.vitamin B6 function as co-carboxylase in the decarboxylation of dopa todopamine.essential for protein metabolismessential for the formation of hemoglobin, the pigment in the blood that carriesoxygen around the body.essential for utilization of proteins and fatshelps in normal function of nervous systemis needed also by certain bacterianecessary for production of red blood cells and antibodies which fight diseaseneeded for many body functions
  • Decarboxylation of amino acidsTransaminase reactionsRacemization reactionsAldol cleavage reactionsTransulfuration reactionsConversion of tryptophan to niacinConversion of linoleic acid into arachidonic acid (prostaglandinprecursor)Formation of sphingolipidsSERINE ETHANOLAMINE ACETYLCHOLINETYROSINE DOPA DOPAMINE EPINEPHRINETRYPTOPHAN 5-HT SEROTONINHISTIDINE HISTAMINEGLUTAMIC ACID GAMMA AMINOBUTYRIC ACID (GABA)CYSTEINE CYSTEINE SULFINIC ACID TAURINE- CO2- CO2- CO2- CO2- CO2- CO2(Decarboxylation)Serine-NH3+ H20Pyruvic acid (Elimination)
  • L-Glutamin acidGlutamin acid racemaseD-Glutamic acid.L-DOPA L-DOPA L-dopamineL-dopamineCO2BrainB6 stimulatesthis reaction outsideof the brainuse carbidopa: an inhibitor of DOPA decarboxylasein combination with DOPA: Sinemet 10/100 or Sinemet 25/250Pyridoxine can antagonize the antiparkinsonian use ofL-DOPA
  • NHOH3CCH2OHCH2OHpyridoxineNHOH3CCH2OHCHONHOH3CCH2OHCH2-NH2pyridoxal pyridoxamineNHOH3CCHOCH2 O POOHOHNHOH3CCH2-NH2CH2 O POOHOHpyridoxal phosphate pyridoxamine phosphateNHOH3CCH2OHCOOHpyridoxic acidAcetic anhydrideNH3- CH3OHKmno4Phosphorylationand oxidationto the aldehyde.
  • Synthesis of Pyridoxal and pyridoxamine.
  • vitamin B6 will help maintain the natural colour in your hair -- and ward offgraying.VITAMIN B6 IS USED FORnerve disorderred blood formationbody immunityhand numbnessmetabolism of protein and fatkidney stonesanemiaasthmaconvulsionsdepressionmental retardationpremenstrual syndrome(headache,depression,irritability,weight gain)urticariaIt is used to treat or prevent the deficiency of vitaminB6 deficiency.It is also given in combination with isoniazid and cylcoserine to reducetheir toxicity.It is also used in the treatment of sideroblastic anaemia.Treatment of Hydrazine and isoniazid poisoning.
  • Vitamin B6 is indicated for the treatment of sideroblast anemia, neurologicdisturbances, seborrhoeic dermatitis, and cheilosis. In combination withfolic acid and vitamin B12, vitamin B6 lowers homocysteine levels which isan amino acid linked to heart disease and stroke, and possibly otherdiseases as well, such as osteoporosis, and Alzheimers disease.Pyridoxine is required for the balancing of hormonal changes in women aswell as assisting the immune system and the growth of new cells. VitaminB6 may be helpful in some women with premenstrual dysphoric disorder,also known as premenstrual syndrome (PMS), and may be useful in somecases of gestational diabetes and for protection against metabolicimbalances associated with the use of some oral contraceptives. VitaminB6 promotes iron excretion and this has been used as a rationale fortreatment in iron storage diseases