HOPE CHEM 103 - LECTURE
School name Hope College
Pages 12

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1Vitamins & Supplements• Definition: Vitamins are minute quantities of organic substances essential for the regulation of metabolic processes.• Researchers mistakenly named these minute nutrients as amine containing water soluble substances.• Vita=vital for life•Min=amineA table of vitamin deficiency and overdose data from the web• http://en.wikipedia.org/wiki/VitaminVitamins• Water soluble:– B,C, G, (riboflavin) H (biotin)• Water insoluble:– A, D, E and KAOHRetinol (Vitamin A)2A• Carotene is a provitamin A• It is yellow in color (highly conjugated)• Air oxidation at the right carbon positions (red) will give Vitamin ACaroteneA• Needed for – Growth of tissues– Reproduction– Vision• Deficiency –– Night blindnessA• Accutane for acne treatment is the carboxylic acid of Vitamin AOHOAccutaneB1• Vitamin B1 ((thiamine) the name implies sulfur and amine in the molecule– Water soluble– Found in polishings of yeast and rice (about 5-10 grams from 1 ton of rice)• Deficiency– Beriberi (degeneration and inflammation of the nerves, heart and digestive system)3B1• Thiamine (or a thiazolium salt)NNNSNH2H3CCH3OR+ThiamineR = mon, di or triphosphateCl-Stetter reaction for Lipitor Synthesis• A thiamine catalyst was used in the synthesis of an important intermediate toward the commercial production of Lipitor.B2• Vitamin B2 (riboflavin)– Water soluble– Found in liver, heart and kidney, vegetables and fruits• Deficiency– Impaired growth, dermatitis (pellagra, or lip lesions)B2• Bitter taste (amine)• Yellow color (because it is highly conjugated)4B6•Vitamin B6 (paradoxine)– Water soluble– Found in rice and bran• Deficiency– Pellagra (especially in lesions of the tongue)B6• Folic Acid– Water insoluble– Found in vegetables, liver and yeast • Deficiency– Essential for the growth of red and white blood cells– Implicated in child birth defects in women with folic acid deficiencyB6 (Folic acid) B12 (cobalt complex)• Vitamin B12 (Cobalt amine)– Water soluble– Found in liver• Deficiency– Pernicious anemia (3-6 micrograms per individual is sufficient to prevent this disorder)5B12 Vitamin C• 1535 Jacques Cartier and his sailors were cured by Newfoundland Indians by drinking the extract from spruce tree needles.• 1747, British navel surgeon prescribed lime to sailors to prevent scurvy. Thus the slang limey for British sailor.C• It came from D-glucose, D-galactose or D-glucaric acid. It has the following structure:OOHOH2COHHHO OHl--Ascorbic AcidVitamin C• Vitamin C– Water soluble– Found in fresh fruit and vegetables– White crystalline sour taste (acid)• Deficiency– Scurvy (limey – a nickname for British sailors)6D2H3CCH3CH3CH3HOHCH3Vitamin D2Vitamins & Supplements• Vitamin D– Water insoluble– Found in egg yolk, liver• Deficiency– Vision defectsD• Vitamin D– Water insoluble– Found in egg yolk, liver• Deficiency– Vision defectsVitamins & Supplements• Vitamin E– Water insoluble– Found in egg yolk, liver• Deficiency– Vision defects7Vitamin E• Found in wheat germ, corn, sunflower seeds, soy bean oil, alfalfa and lettuce• Has three chiral centers• Anti-oxidant• Oil solubleOCH3CH3CH3CH3HHCH3HOH3CCH3Vitamin EVitamin EVitamin H (BIOTIN)• It functions as a cofactor for enzyme reactionsHNNHSOOHOHHHBIOTINVitamin H (BIOTIN)• The first commercial process was developed by Leo Sternbach (inventor of Valium and Librium) at Hoffmann-La Roche• Deficiency in human is rare because intestinal flora biosynthesis of biotin from cysteine.• Deficiency symptoms are dermatitis, weight loss and loss of appetite.8Vitamin K1 and K2OOCH3H3CCH33Vitamin K1CH2OOCH34Vitamin K2HVitamin K1 and K2• Found in green vegetables• Promote blood clottingThe top 50 most prescribed drugs• http://www.3dchem.com/top50.aspDrugs for common aches and pains• NSAID (Non-Steroidal Anti-inflammatory Drugs) commonly OTC products such as Aspirin, Tylenol, Midol etc.9Aspirin• Invented by Author Eichengruen in Bayer in 1897• John Vane in 1971 published the paper on aspirin and related products on inhibition of prostaglandin synthesis (1982 Nobel laureate in Physiology)COX 2 InhibitorsOOSOOVIOXX $2.5 B in 2002NNSH2NOOCF3CELEBREX $1.5 B in 2002COX 2 inhibitors• Cyclooxygenase 2 inhibitors• They also prevent the biosynthesis of prostaglandins, thus reduce pain.• They are more gentle on the stomach thus avoid the common side effects of stomach bleeding of NSAIDMorphine analogsOH3CO OCH3NOH3CONOHHOH3CONOOHOXYCODONTHEBAINECODEINEwith aspirin is Percodanwith acetaminophen is Percocetwith ibuprofen is OxyContin10Morphine• These are extremely habit forming• The most abused drug in the US• Heroin is derived from morphineDrugs historyfor hypertensionACE inhibitor• The discovery of Captopril (1981)• 1960 John Vane discovered the pit viper venom to be an angiotensin II inhibitorOther ACE inhibitors2002 sales value MM$• Accupril (Quinapril) Parke-Davis 706• Altace (Ramipril) King Pharma 527• Zestril (Lisinopril) Astra Zeneca 478 • Lotensin (Benazepril) Novartis 483• Captopril Bristol Myer and generics<100Drugs history• Cows feeding on sweet clover were dying from internal bleeding (over 100 year ago)• U of Wisconsin ag school found the active material named it after the Wisconsin Alumni Research Foundation (WARF)• Warfarin (coumadine) a rat poison as well as a blood thinner for DVT11WarfarinOOOOHWarfarinCoumadineAntibiotics• Beta lactams (penicillin)• It discrupt the gram positive bacteria cell wallProblems in penicillin• Allergy/hypersensitivity• Allergicreactions to any β-lactam antibiotic may occur in up to 10% of patients receiving that agent. Anaphylaxiswill occur in approximately 0.01% of patients• Resistance to penicillin because of misuse.Other anti-infectives• Macrolides• Erythromycin12Azithromycin• This is a second generation erythromycinAnti-infective• Linezolide (invented by Upjohn scientists)Linezolide• Also known as Zyvox• Came on the market in 2000• 2003 bacteria resistance was


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HOPE CHEM 103 - LECTURE

Course: Chem 103-
Pages: 12
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