Med Chem 3 Exam 2
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- Competitively inhibit enzyme dihydropteroate synthetase
- PABA Antagonists
- Bacteria cannot absorb
- folic acid
- Simplest sulfonamide structure, topical use
- Sulfanilamide
-
Prodrug. Azo compound reduced in vivo to
sulfapyridine (PABA antagonist) and mesalamine (antiinflamatory) - Sulfasalazine
- Indicated for Crohn’s Disease
- Sulfasalazine
- Prodrug. Metabolised in vivo to Cycloguanil (the inhibitor)
- Proguanil
- Mechanism of Isoniazid
- Mycolic acid synthesis inhibitor
- Undesired side effect - forms Shiff base with Vitamin B6
- Isoniazid
- Mechanism of Pyrazinamide
- lowers pH
- Mechanism of Ethambutol
- Unknown, inhibits RNA synthesis
- Mechanism of Aminosalicylic Acid
- PABA competitive inhibitor
- Mechanism of Ethionamide
- Unknown, bacterial protein synthesis inhibitor
- Mechanism of Cycloserine
- Bacterial cell wall synthesis inhibitor, competes with D-alanine
- Mechanism of Capreomycin
- Unknown, protein synthesis inhibitor, binds 30S ribosome(?)
- Cross-resistance with aminoglycoside antibiotics
- Capreomycin
- Mechanism of Rifapentine
- Inhibitor of DNA-dependent RNA polymerase
- 10x more potent than rifampin for TB
- Rifapentine
- Treatment for TB which induces CYP3A4. Many drug interactions
- Rifapentine
- Mechanism of Dapsone
- PABA competative inhibitor
- Mechanism of Clofazimine
- Binds preferentially to mycobacterial DNA
- Mechanism of Rifampin
- DNA-dependent RNA polymerase inhibitor
- Mechanism of Thalidomide
- Tumor necrosis factor (TNF) inhibitor
- Red color - tan or black in human tissue
- Clofazimine
- Treated with Dapsone
- Leprosy
- Treated with Clofazimine
- Leprosy
- Treated with Rifampin
- Leprosy
- Treated with Thalidomide
- Leprosy
- Treated with Ethionamide
- Leprosy and Tuberculosis
- Treated with Isoniazid
- Tuberculosis
- Treated with Pyrazinamide
- Tuberculosis
- Treated with Ethambutol
- Tuberculosis
- Treated with Aminosalicylic Acid
- Tuberculosis
- Treated with Cycloserine
- Tuberculosis
- Treated with Capreomycin
- Tuberculosis
- Treated with Rifapentine
- Tuberculosis
- Drugs which treat fungi and disrupt the cell membrane
-
Amphotericin-B
Nystatin
Micafungin - Treats fungi; selective for ergosterol-containing membranes, increases cell potassium loss, and is orally active
- Amphotericin-B
- Treats fungi; selective for ergosterol-containing membranes, increases cell potassium loss, and is NOT orally active
- Nystatin
-
Inhibits synthesis of 1-3-beta D-glucan,
a component of fungal cell wall - Micafungin
- Echinocandin lipopeptide
- Micafungin
- Mechanism of Ketoconazole
- Inhibits ergosterol synthesis
- Mechanism of Econazole
- Inhibits ergosterol synthesis
- Mechanism of Clotrimazole
- Inhibits ergosterol synthesis
- Mechanism of Fluconazole
- Inhibits ergosterol synthesis
- Mechanism of Itraconazole
- Inhibits ergosterol synthesis
- Mechanism of Terconazole
- Inhibits ergosterol synthesis
- Mechanism of Voriconazole
- Inhibits ergosterol synthesis
- Mechanism of Terbinafine
- Inhibits ergosterol synthesis
- Mechanism of Butenafine
- Inhibits ergosterol synthesis
- Mechanism of Naftifine
- Inhibits ergosterol synthesis
- Imidazoles, P450 inhibitors, orally active
-
Miconazole
Ketoconazole
Econazole - Imidazole, P450 inhibitor, topical, NOT orally active with extra benzene ring
- Clotrimazole
- Triazoles, P450 inhibitors, orally active
-
Fluconazole
Itraconazole
Terconazole
Voriconazole - Non-P450 mechanism, Squalene epoxidase inhibitor, oral
- Terbinafine
- Non-P450 mechanisms, Squalene epoxidase inhibitors, NOT oral
-
Butenafine
Naftifine - Anti-fungal drug which is converted to 5-fluorouracil by a fungal enzyme
- Flucytosine
- Anti-fungal drug which disrupts mitotic spindle which inhibits mitosis
- Griseofulvin
- Anti-worm drug which inhibit ATP synthesis and oxidative phosphorylation
- Niclosamide
- Drugs which treat Cestodes
- Niclosamide and Oxamniquine
- Treats beef, fish, and dwarf tapeworm
- Niclosamide
- Works against shistosomes
- Oxamniquine
- Known mechanism of Oxamniquine
- Makes female worms unable to lay eggs and they explode
- Unknown mechanism of Oxamniquine
- kills males
- Treatments for trematodes
-
Praziquantel
Bithional - Increase cell calcium loss leading to worm paralysis
- Praziquantel
- Treatment for tapeworm
- Praziquantel
- Treatment for lung or liver flukes
- Bithional
- Treatment for pin, whip, round, or hookworms
- Mebendazole
- Treatment for threadworms or trichinosis
- Thiabendazole
- Treatment for round worm
- Pyrantel
- Treatment for filariasis
- Diethycarbamazine
- Treatment for adult filariasis
- Suramin
- Treatment for river blindness
- Ivermectin
- Damages protective cuticle and inhibits worm egg formation
- Bithional
- Three drugs which lead to worm paralysis
- Praziquantel, Ivermectin and Pyrantel
- Blocks worm glucose and nutrient uptake and kills selectively
- Mebendazole
- Mitochondrial fumurate reductase inhibitor which kills selectively
- Thiabendazole
- Cholinesterase inhibitor which releases acetylcholine and works in gi tract toparalyzes worms
- Pyrantel
- Utilizes an unknown mechanism to immobilize worms and make their surface membranes more susceptible to host defense mechanisms
- Diethycarbamazine
- Worm treatment which binds GABA receptors leading to worm paralysis
- Ivermectin
- Drug which is worm selective
- Mebendazole
- Inhibits oxidative phosphorylation which inhibit DNA and RNA synthesis in protozoa
- Pentamidine
-
Inhibits ornithine decarboxylase
which inhibit polyamine synthesis in protozoa - Eflornithine
- Blockades electron transport by unknown mechanism in protozoa
- Atovaquone
- dihydrofolate reductase inhibitor in protozoa; selective antidote
- Trimetrexate / Leucovorin
-
Prodrug, reduced form binds DNA
increases DNA breakage in protozoa - Metronidazole
- Have unknown mechanisms to treat Amoebiasis
- Diloxanide, Iodoquinol and Emetine / Dehydroemetine
- Poorly absorbed drug which treats Amoebiasis
- Iodoquinol
- Prodrug to diloxanide
- Diloxanide Furoate
-
Aminoglycoside, poorly absorbed
40S ribosome binder, inhibits protein synthesis, treats Amoebiasis - Paramomycin
- All drugs which treat Giardiasis have this mechanism
- The mechanism is unknown
- Treatments for Giardiasis with reversible yellowing of skin, resembles clofazimine
- Quinacrine and Acranil
- Treatment for Giardiasis which forms a Shiff base, used for children
- Furazolidine
- Treatment for Giardiasis with unknown antiinflammatory action
- Tinidazole
- Treatment for Giardiasis in Treatments for Giardiasis
- Paramomycin
- Treatment for Lishmaniasis with Pentavalent antimony and unknown mechanism
- Sodium Stibogluconate
-
Two treatments for Lishmaniasis which inhibits
oxidative phosphorylation of and interfers with the incorporation of nucleic acids into RNA and
DNA in protozoa - Pentamidine and Stibamidine
- Effective for treatment of lishmiasis resistent to antimonial drugs
- Pentamidine and Stibamidine
- Arsenic drug which treats Trypanosomiasis
- Melarsoprol
- Treatment for Trypanosomiasis which inhibits energy metabolism enzymes
- Suramin
- Treatment for Trypanosomiasis which works just like Pentamidine and Stibamidine
- Eflornithine
- Treatment for Trypanosomiasis which forms a Shiff base, like furazolidine, for cardiac muscle
- Nifurtimox / cortisone
- Treatment for Trypanosomiasis which is antiinflamatory, and works like tinidazole
- Benznidazole
- Two treatments for Malaria which raises internal pH, inhibits DNA synthesis
- Chloroquine and Mefloquine
-
Treatment for Malaria which inhibits oxygen uptake and
metabolism disturbs calcium distribution - Quinine
- Chloroquine, Quinine and Mefloquine treat
- blood shizonts
- Treatment for malaria which disrupts mitochondria, binds DNA G6PD
- Primaquine
- Treatment for malaria with hemolysis side effect
- Primaquine
- Treatment for malaria which is good to prevent relapses
- Primaquine
- Treatment for malaria which is a prodrug to dihydrofolate reductase inhibitor
- Proguanil
- Treatment for malaria which is a dihydrofolate reductase inhibitorwhich inhibits thymidine synthesis
- Pyrimethamine
- Tetracycline-like, IV only, not used during tooth development
- Glycylcycline class
-
Anti-metabolites
such as folate antagonists are classified as - Protein synthesis inhibitors
- It deactivates and is deactivated by vitamin B6
- Isoniazid
-
Acts by inhibiting
mycolic acid synthesis, a unique mechanism - Isoniazid
- Similar to amphotericin B but lacks double bond and folds up in water
- Nystatin
- Inhibits glucan synthesis, made of six peptides cyclized, given by injection only
- Echinocandin lipopeptide
-
Kill parasites while they
reproduce asexually in the liver, before entry into the red blood cells - Tissue schizonticides
- Destroy parasite in the red blood cells and can cure or prevent relapse of malaria
- Blood schizonticides
- Basis for selectivity of PABA inhibitors
- Inability of bacteria to absorb folic acid
-
Selectively toxic because major cell membrane sterol
is cholesterol in humans and not ergosterol in fungi - Amphotericin B
-
Converted in fungal cells, but not in human cells,
into 5-fluorouracil (5-FU) - Flucytosine
- Competitive inhibitors of dihydropteroate synthetase
- Sulfonamides
- Pharmacodynamically selective
- Sulfonamides
- Required for activity of sulfonamides
- Proton on the sulfonamide nitrogen
- Sulfonamides exhibit optimal activity when the pKa of the sulfonamide N hydrogen is between
- 6 and 8
- The haptophore of sulfonamides minic PABA while the toxophile
- competes with PABA for a binding site
- For sulfonamides the haptophore is equal to the
- toxophile
-
Sulfamethoxazole is used with
Trimethoprim because - They both have similar pattern of distribution and rate of elimination
-
Sulfamethoxazole with
Trimethoprim is marketed as - Co-trimoxazole
- Drugs which inhibit the synthesis or utilization of folic acid are called
- Antimetabolites
- The most common predisposing factors to fungal growth in humans
-
Use of broad-spectrum
antibiotics - Upon biting the mosquito sporozites enter the body and infect the
- Liver
- Symptoms of malaria are present about every 48 hours due to
- bursting of red blood cells
- dormant parasites are called
- hypnozoites
-
The depolarizing
neuromuscular blocking action of this drug overwhelms the worm’s nicotinic receptors and causes paralysis. - Pyrantel pamoate