MedChem Exam I

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MedChem Exam I
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2012-02-07 11:46:27
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  1. Chloromycetin
    • Chloramphenical
    • Carrier Linked Prodrug, drugs that are attached through a metabolically labile chemical linkage to another molecules designated as the promoiety

    • Esterase or water cleaves off the sodium succinate making it an active drug
    • serious infections, monitor for blood dyscrasiasfac

    Alcohol hydroxyl oxygen gluconrides
  2. Emcyst
    Estermustine Sodium Phosphate

    Mutual Prodrug, Carrier linked prodrug in which the promeity is also a drug

    The products are sodium phosphate and nornitrogen mustard --> Aziridine

    Used to treat of progressive or metstatic carcinoma of the prostate
  3. Erthromycin
    • Antobiotic used to treat upper and lower respiratory infections, legionnaire's disease skin infections
    • Very bitter substance and easily destroyed at acidic pH

    Add two functional groups

    Prodrug

    Propionate ester to increase lipid solubility

    Lauryl sulfate salt, absorption not affected by food, less bitter after taste and is acid stable
  4. Beta Lactam antibiotics, penicillins and cephalosporins
    Penicillin have the beta lactam ring with the r group as the prodrug, with the r being ethyl, propyl, butyl, phenyl group that needs to be cleaved for it to be active

    Esterase cannot cleave by itself needs to be be an double ester for esterase to act on it, cleaves the carbonate and then the ester spontaneously leaves leaving the active drug

    Taking with food increases absorption
  5. Rolitetetracycline
    Amine derivatives as prodrugs

    Tetracycline with increased water solubility

    Tetracycline Reacts with formaldehyde to form rolitetracyline
  6. Azulfidine
    • Sulfasalazine
    • Azolinkage as a prodrug
    • Sulfoamide antibiotic and anitinflammatory used to treat ulcerative colitis, rheumatoid arthritis
    • Bacterialreductase lead to reductive cleavage releasing 2 amine compounds
    • occurs in the colon: discourages small intersinte systemic absorption and concentrates the drug at the desired site of absorption
  7. Hiprex, Urex
    • Methenamine hippurate
    • Carboonyl compound derivative as prodrugs
    • USed for prophylaxis or suppression/elimination of frequent UTI espeially for long term use
    • The lower the pH the faster the rate of formation of formaldehyde in the urine in the blood sream
  8. Relafen
    • Nabumetone
    • Bioprecursor prodrugs, oxidation example, do not contain promeity, they contain latent functionality that is metabolically or chemically transformed into an active drug
    • Non-steroidal antiinflammatory, arthritis
    • Active form of drug that inhibits prostaglandin biosynthesis by cyclooxygenase
  9. Mutamycin
    • Mitomycin
    • Bioprecursor prodrug, reduction example
    • Oncology for use in Adenocarcinoma of the stomach and pancreas
    • A quinone, reduction, to hydroquinone, loss of OCH3, loss of H+, Loss of CO2 and NH3, Further alkylation for the active drug
  10. Herplex
    • Iodoxuridine
    • Bioprecursor prodrug phosphylation example
    • Has halogen makes it lipid soluble
    • Opthalmic product for herpes simplex keratitis, higher affinity for viral kinases than mammalian kinases but some toxcity

    Two mechanisms of actions: inhibits DNA polymerase, causing incorrect base pairing
  11. Levodopa-Carbabdopa
    • Anti-Parkinsonism agent
    • Dopamine does not cross the blood brain barier efficiently is rapidly metabolized bu oxidatvie deamination and can cause peripherial side effects


    Methylation conjugation
  12. pharmacokinetics
    how the drugs are processed by the body
  13. pharmakodynamics
  14. includes how drugs interact with receptor on cells to cause a response
    how the drug works on the body
  15. Enzyme induction
    • compounds that enhance metabolism
    • phenobarbitol, carbamazepine, rifampin
  16. Glutethimide
    • A piperidine based sedative hypnotic
    • two different enatiomers with different effects
  17. Dilantin
    Phenytoin

    • Steroselective that is an oxidative process hydroxylation
    • there are two different enatiomers 90%of one and 10%of the other
  18. Pavabid
    • Papaverine
    • Regioselective metabolism: refers to selective meabolism of one or 2 or more of the same functional group within a part of a molecule: has four OMe groups for the demethylation to occur, the methyl group that is next to the heteroatom
    • Smooth muscle relaxer used as a peripherial vasodilator
  19. Phase1 metabolism
    • Primarily oxidative with functional group changes mediated principally by Cytochrome P450
    • Addition of a polar functional group
  20. Phase 2
    • Conjugating enzymes that usually add a hydrophilic molecules o drug o a phase 1 etabolite
    • to increase water solubility
  21. Phase 3
    Efflux pump systems that facilitate the remval of the meabolites from cells to the urine or bile
  22. Salicyclamide
    With normal amount of drug there is very low concentration of drug needs to saturate the first pass effect, once the first pass effect enzymes are saturated then normal concentration of drug are seen
  23. Xylocaine
    • Lidocaine
    • First pass effect exampl of de-ethylation, oxidative dealkylation
    • Not useful for treatment of ventricular arrhythmias since activity is lost upon first pass effect throught the liver due to inactivityof the two de ethylated metabolites
    • Tertiary aliphatic and alicyclic amines
  24. Valium
    • Diazepam
    • Oxidation reactions
    • Selectivity: oxidation occurs at the most electron rich carbon, on the benzene ring


    Oxidation at alpha carbon loated next to carbonyls and imines



    Oxidation of Amides- Hydroxylation alpha to the amine nitrogen product of desmethylDiazepam
  25. Tegretol
    • Carbamazepine
    • Oxidation of carbon carbon double bonds: OLEFINS
    • Leading to epoxides, then 1,2 diols
    • Subjuct to glutathione conjugation
    • Primary drug for partial and clonic tonic seizures
    • 30% urinary metabolites with the balance as glucuronide conjugates
    • POtent anticonvulsant activity
  26. Seconal
    • Secobarbitol
    • Olefinic Oxidation
    • both process via an intermediate epoxide
    • Two metabolites Secodiol, P450 Heme Nitrogen
    • The P450 Heme Nitrogen has irreversible destruction and leads to liver failure
  27. Lopressor
    • Metoprolol
    • Benzylic oxidation
    • Beta adrenergic blocker
  28. Tolectin
    • Tolmetin
    • Benzylic oxidation
    • Anti-inflammatory analgesic
  29. Talwin
    • Pentazocine
    • Oxidation at Allylic Carbons: allylic carbon is the carbon adjacent to carbon-carbon double bound
    • Narcotic used for pain or pre/post operative anesthesia
  30. Quinidine
    • Quinidex Extentabs (sulfate salt)
    • Quinagulate Dura-Tabs (sulfate salt)
    • Quinalan (gluconate salt)
    • Cardioquin (gluconate salt)
    • Oxidation at allylic carbons
    • antiarryhthmic
  31. Hexobabitol
    oxidation at allylic carbons
  32. Serax
    • Oxaepam
    • Oxidation at alpha carbon located next to carbonyls and imines
    • antianxiety
  33. Glutethimide
    • Oxidation at alpha carbon located next to carbonyls and imines
    • 3-7days for insomnia Schedule II
  34. Diabinese
    • Chlorpropamide
    • Oxidation at aliphatic carbons
  35. Haltran, Mednadol Nuprin
    • Ibuprofen
    • Oxidation at aliphatic carbons
    • Non-steroidal antiinflammatory
  36. Dymelor
    Acetohexamide

    • Oxidation at alicyclic carbons
    • Oral antidiabetic agent
    • a sulfonylurea
  37. Loniten, Rogaine
    • Minoxidil
    • Oxidation at alicyclic carbons
    • Severe unresponsive hypertension
    • Male pattern baldness
  38. Thorazine
    • Chlorpromazine
    • Tertiary aliphatic and alicyclic amines
  39. Phenothiazine
    • Tertiary aliphatic and alicyclic amines
    • antiemetic, antivertigo, antipsychotic
    • bad n/v
  40. Inderal
    • Propranolol
    • Oxidation of secondary and primary amines
    • a non selective beta0adrenergic blocking agent
  41. Ritalin
    • Methylphenidate
    • Oxidation of secondary and primary amines
    • USed for atentiondeficit disorders and narcolepsy
  42. Phentermine
    • Ionamin, Adipex-p, Zantryl, Fastin
    • Oxidation fo secondar and primary amines
    • Managemnt of obesity
  43. dl Amphetamine sulfate
    • Oxidation of secondary and primary amines
    • Attention deficit disorder
    • narcolepsy
    • Remember n-hydroxy compounds are chemicaly unstable
  44. Trimpex, Proloprim, Combo with antibiotics Bactrim Septra Cotrim
    • Trimethoprim
    • Oxidation of NItrogen Hetercycles
    • Dihydrofolate reducatase inhibitor
  45. Nosar, Cytoxan
  46. Cyclophosphamide
    • Oxidation of Amides- Hydroxylation alpha to the amine nitrogen
    • Alkylating agent
  47. Pentathol
    • Thiopental
    • Oxidation of carbon sulfur bonds
    • INduces anethesia to get you through tage 1 of anesthesia
    • MEtabolite pentobarbitol
  48. Mellaril
    • THrioridazine
    • Sulfur oxidation
    • antipsycotic, tranuilizer
    • Metabolite: mesoridazine = serentil
  49. Fluothane
    • Halothane
    • Oxidative dehalognations
    • General anethetic
    • Hepatic Damane
  50. NOrgestrel
    • Oxidative aromatization or dehydration
    • A progstin used in OC's
    • AROMATASE
  51. Coumadin
    • Warfarin
    • Bioreduction fo ketones is often sterospecific or steroselective for one isomer over the other
    • Has two diasteromer a major and minor
    • Anticoagulant

    Enol oxygen glucuronides
  52. Dantrium
    • Dantrolene
    • REduction of NItro and Azo compounds
    • Direct acting skeletal muscle relaxant
  53. Antabuse
    • Disulfiram
    • Disulfate bond cleavage
    • Treatment of chronic alcoholism
  54. Clinoril
    • Sulindac
    • Cleavage of sulfoxide group
    • Non-steroidal antiinflammatory
  55. Atromid-S
    • Clofibrate
    • Hydrolysis of esters
    • Antihyperlipidemic agent
  56. Minipress
    • Prazosin
    • Hydrolysis of amides
    • Amides are more difficult to hydrolyze relative to esters
    • Antihypertensive, alpha1 adrenergic blocker
  57. Acetaminophen
    • APAP, N-acetyl-p-aminophenol
    • Phenol hydroxyl glucuronides
  58. Nalfon
    • Fenoprofen
    • Carboxylate hydroxyl glucuronide
    • Non-steroidal anti-inflammatory
  59. Dapsone
    • N-hydroxy metabolite
    • N-hydroxyl glucuronide
    • USed in treatment of leprosy, pneumocystis carinni pneumonia

    BROWN RECLUSE SPIDER BITES
  60. Aldomet
    • alpha-methyldopa
    • Sulfate conjugation
    • antihypertensive
  61. Proventil
    • Albuterol
    • Sulfate conjugation
    • A sympathomimetic bronchodilator
    • USed for treatment for bronchospasms in COPD
  62. Laniazid
    • Isoniazid
    • Conjugation with glycine
    • Antituberculosis
  63. Nitroglycerin
    • glutathione nuclephilic displacement conjugation
    • A nitrate vasodilator for the treatment and prophylaxis of angina pectoris
  64. Imuran
    • Azathioprine
    • glutathione nucleophilic displacement conjugation
    • Immunosuppressant for the treatment of transplantation and rheumatoid arthritis
  65. Edecrin
    • Ethacynic Acid
    • Glutathione Michael Addition conjugation
    • Loop diuretic used edema from CHF renal nd hepatic disease
  66. Klonopin
    Clonazepam

    • N-acetylation conjugation
    • anticonvulsant benzodiazepine
  67. Apresoline
    • Hydralazine
    • N-acetylation conjugation
    • Antihypertensive vasodilator
  68. Berthaire, Brethine, Bricanyl
    • Terbutaline
    • Methylation conjugation
    • Asympathomimetic brchodilator
  69. Symmetrel
    • Amantadine HCL
    • N-methylation conjugation
    • Anitparkinsonism and antiviral
  70. Propylthiouracil
    • S-methylation conjugation
    • Used for hyperthyroidism mainly by preventing T3 and T4 synthesis

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