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ANT-HELMINTICS:- PDF/PPT

Description

Subject:- Medicinal chemistry 2

Semester:- 5th sem

Course:- Bachelor of Pharmacy B Pharmacy

     Medicinal Chemistry-IIl




ANT-HELMINTICS
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                           ANTHELMINTICS
• ANTHELMINTICS ARE DRUGS THAT HAVE THE CAPABILITY OF RIDDING THE BODY OF
  PARASITIC WORMS OR HELMINTHS
• HELMINTHS THAT INFECT HUMAN HOSTS ARE DIVIDED INTO TWO CATEGORIES, OR
  PHYLA:
• A) PLATYHELMINTHES (FLATWORMS)- INCLUDE THE CLASSES CESTODE
  (TAPEWORMS) AND TREMATODE (FLUKES OR SCHISTOSOMES)
• B) ASCHELMINTHES OR NEMATODES (ROUNDWORMS)- ROUNDWORM,
  HOOKWORM, PINWORM, AND WHIPWORM. THESE WORMS ARE CYLINDRICAL IN
  SHAPE, WITH SIGNIFICANT VARIATIONS IN SIZE, PROPORTION, AND STRUCTURE


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                               ANTHELMINTICS
• NEMATODE INFECTIONS
• ANCYLOSTOMIASIS OR HOOKWORM INFECTION- AMERICAN HOOKWORM (NECATOR
  AMERICANUS) AND THE “OLD WORLD” HOOKWORM (ANCYLOSTOMA DOUDENALE).
• ENTEROBIASIS OR PINWORM INFECTION- ENTEROBIUS VERMICULARIS
• ASCARIASIS OR ROUNDWORM INFECTIONS- ASCARIS LUMBRICOIDES
• TRICHURIASIS OR WHIPWORM INFECTIONS- TRICHURIS TRICHIURA
• TRICHINOSIS OR TRICHINA INFECTION- TRICHINELLA SPIRALIS
• FILARIASIS- WUCHERERIA BANCROFTI, BRUGIA MALAYI, AND BRUGIA TIMORI




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                         ANTHELMINTICS

• CESTODE AND TREMATODE INFECTIONS
• CYSTICERCOSIS OR TAPEWORM INFECTION
• BEEF TAPEWORM (TAENIA SAGINATA)
• PORK TAPEWORM (TAENIA SOLIUM)
• DWARF TAPEWORM (HYMENOLEPIS NANA)
• FISH TAPEWORM (DIPHYLLOBOTHRIUM LATUM)
• SCHISTOSOMIASIS OR BLOOD FLUKES- SCHISTOSOMA HEMATOBIUM,
  SCHISTOSOMA MANSONI, AND SCHISTOSOMA JAPONICUM


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                         DIETHYLCARBAMAZINE CITRATE
• HIGHLY WATER-SOLUBLE CRYSTALLINE COMPOUND THAT HAS SELECTIVE ANTHELMINTIC
  ACTIVITY
• IT IS EFFECTIVE AGAINST VARIOUS FORMS OF FILARIASIS, INCLUDING BANCROFT,
  ONCHOCERCIASIS, AND LAVIASIS
• IT IS ALSO ACTIVE AGAINST ASCARIASIS
• MECHANIM- NOT CLEARLY KNOWN
• SUGGESTION- INHIBITION OF MICROTUBULE POLYMERIZATION AND DISRUPTION OF
  PREFORMED MICROTUBULES
• OR INTERFERENCE WITH ARACHIDONIC ACID METABOLISM
• ADVERSE REACTIONS- ANAPHYLACTIC REACTIONS, INTENSE PRURITUS, AND OCULAR
  COMPLICATIONS

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                            THIABENDAZOLE
• OCCURS AS A WHITE CRYSTALLINE SUBSTANCE THAT IS ONLY SLIGHTLY SOLUBLE IN
  WATER BUT IS SOLUBLE IN STRONG MINERAL ACIDS.
• THIABENDAZOLE IS A BASIC COMPOUND WITH A PKA OF 4.7 THAT FORMS
  COMPLEXES WITH METAL IONS
• MECHANISM- INHIBITS THE HELMINTH-SPECIFIC ENZYME FUMARATE REDUCTASE
  (IMPORTANT ENZYME IN HELMINTHES THAT APPEARS TO BE INVOLVED IN
  OXIDATION OF NADH TO NAD FOR ATP PRODUCTION)
• ALSO ARREST NEMATODE CELL DIVISION IN METAPHASE BY INTERFERING WITH
  MICROTUBULE ASSEMBLY AND EXHIBIT A HIGH AFFINITY FOR TUBULIN, THE
  PRECURSOR PROTEIN FOR MICROTUBULE SYNTHESIS

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                           THIABENDAZOLE
• HAS BROAD-SPECTRUM ANTHELMINTIC ACTIVITY
• IT IS USED TO TREAT ENTEROBIASIS, STRONGYLOIDIASIS (THREADWORM
  INFECTION), ASCARIASIS, UNCINARIASIS (HOOKWORM INFECTION), AND
  TRICHURIASIS (WHIPWORM INFECTION)
• ALSO USED TO RELIEVE SYMPTOMS ASSOCIATED WITH CUTANEOUS LARVA
  MIGRANS (CREEPING ERUPTION) AND THE INVASIVE PHASE OF TRICHINOSIS.
• WIDELY USED IN VETERINARY PRACTICE TO CONTROL INTESTINAL HELMINTHS IN
  LIVESTOCK




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                                 MEBENDAZOLE
• BROAD-SPECTRUM ANTHELMINTIC THAT IS EFFECTIVE AGAINST VARIOUS NEMATODE
  INFESTATIONS, INCLUDING WHIPWORM, PINWORM, ROUNDWORM, AND HOOKWORM
• MECHANISM- IRREVERSIBLY BLOCKS GLUCOSE UPTAKE IN SUSCEPTIBLE HELMINTHS,
  THEREBY DEPLETING GLYCOGEN STORED IN THE PARASITE
• IT APPARENTLY DOES NOT AFFECT GLUCOSE METABOLISM IN THE HOST. IT ALSO INHIBITS
  CELL DIVISION IN NEMATODES
• POORLY ABSORBED BY THE ORAL ROUTE


• ADVERSE REACTIONS ARE UNCOMMON AND USUALLY ABDOMINAL DISCOMFORT
• IT IS TERATOGENIC IN LABORATORY ANIMALS AND SHOULD NOT BE GIVEN DURING
  PREGNANCY


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                             ALBENDAZOLE
• BROAD-SPECTRUM ANTHELMINTIC THAT IS NOT CURRENTLY MARKETED IN NORTH
  AMERICA
• WIDELY USED THROUGHOUT THE WORLD FOR THE TREATMENT OF INTESTINAL
  NEMATODE INFECTION
• IT IS EFFECTIVE AS A SINGLE-DOSE TREATMENT FOR ASCARIASIS, NEW AND OLD
  WORLD HOOKWORM INFECTIONS, AND TRICHURIASIS
• MULTIPLE-DOSE THERAPY WITH ALBENDAZOLE CAN ERADICATE PINWORM,
  THREADWORM, CAPILLARIASIS, CLONORCHIASIS, AND HYDATID DISEASE
• EFFECTIVENESS OF ALBENDAZOLE AGAINST TAPEWORMS (CESTODES) IS
  GENERALLY MORE VARIABLE AND LESS IMPRESSIVE
• WHITE CRYSTALLINE POWDER THAT IS VIRTUALLY INSOLUBLE IN WATER

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                           ALBENDAZOLE


• ORAL ABSORPTION OF ALBENDAZOLE IS ENHANCED BY A FATTY MEAL
• DRUG UNDERGOES RAPID AND EXTENSIVE FIRST-PASS METABOLISM TO THE
  SULFOXIDE, WHICH IS THE ACTIVE FORM IN PLASMA
• ELIMINATION HALF-LIFE OF THE SULFOXIDE RANGES FROM 10 TO 15 HOURS
• HIGH DOSE CAN RESULT IN ADVERSE EFFECTS SUCH AS BONE MARROW
  DEPRESSION, ELEVATION OF HEPATIC ENZYMES, AND ALOPECIA




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                                  NICLOSAMIDE
• OCCURS AS A YELLOWISH WHITE, WATER-INSOLUBLE POWDER
• POTENT TAENIACIDE THAT CAUSES RAPID DISINTEGRATION OF
  WORM SEGMENTS AND THE SCOLEX
• PENETRATION OF THE DRUG INTO VARIOUS CESTODES APPEARS TO
  BE FACILITATED BY THE DIGESTIVE JUICES OF THE HOST
• NICLOSAMIDE IS WELL TOLERATED FOLLOWING ORAL
  ADMINISTRATION, AND LITTLE OR NO SYSTEMIC ABSORPTION OF IT
  OCCURS
• A SALINE PURGE 1 TO 2 HOURS AFTER INGESTION OF THE
  TAENIACIDE IS RECOMMENDED TO REMOVE THE DAMAGED SCOLEX
  AND WORM SEGMENTS- MANDATORY


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                                   OXAMNIQUINE
• ANTISCHISTOSOMAL AGENT THAT IS INDICATED FOR THE TREATMENT OF SCHISTOSOMA
  MANSONI (INTESTINAL SCHISTOSOMIASIS) INFECTION
• MECHANISM- SHOWN TO INHIBIT DNA, RNA, AND PROTEIN SYNTHESIS IN SCHISTOSOMES
• 6-HYDROXYMETHYL GROUP IS CRITICAL FOR ACTIVITY;
• METABOLIC ACTIVATION OF PRECURSOR 6-METHYL DERIVATIVES IS CRITICAL
• FREE BASE OCCURS AS A YELLOW CRYSTALLINE SOLID THAT IS SLIGHTLY SOLUBLE IN
  WATER BUT SOLUBLE IN DILUTE AQUEOUS MINERAL ACIDS AND SOLUBLE IN MOST
  ORGANIC SOLVENTS
• DIZZINESS AND DROWSINESS ARE COMMON, BUT TRANSITORY, SIDE EFFECTS
• SERIOUS REACTIONS, SUCH AS EPILEPTIFORM CONVULSIONS, ARE RARE



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                               PRAZIQUANTEL
• BROAD-SPECTRUM AGENT THAT IS EFFECTIVE AGAINST VARIOUS TREMATODES
  (FLUKES)
• IT HAS BECOME THE AGENT OF CHOICE FOR THE TREATMENT OF INFECTIONS
  CAUSED BY SCHISTOSOMES (BLOOD FLUKES)
• EFFECTIVE TREATMENT FOR FASCIOLOPSIASIS (INTESTINAL FLUKE), CLONORCHIASIS
  (CHINESE LIVER FLUKE), FASCIOLIASIS (SHEEP LIVER FLUKE), OPISTHORCHOSIS (LIVER
  FLUKE), AND PARAGONIMIASIS (LUNG FLUKE)
• MECHANISM- INCREASES CELL MEMBRANE PERMEABILITY OF SUSCEPTIBLE WORMS,
  RESULTING IN THE LOSS OF EXTRACELLULAR CALCIUM. MASSIVE CONTRACTIONS
  AND ULTIMATE PARALYSIS OF THE FLUKE MUSCULATURE OCCURS, FOLLOWED BY
  PHAGOCYTOSIS OF THE PARASITE


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                            PRAZIQUANTEL

• ORAL ADMINISTRATION, ABOUT 80% OF THE DOSE IS ABSORBED
• DRUG IS RAPIDLY METABOLIZED IN THE LIVER IN THE FIRST-PASS
• WHITE CRYSTALLINE SOLID THAT IS INSOLUBLE IN WATER




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                                IVERMECTIN
• IS A MIXTURE OF 22,23-DIHYDRO DERIVATIVES OF AVERMECTINS B1A AND B1B PREPARED BY
  CATALYTIC HYDROGENATION
• AVERMECTINS ARE MEMBERS OF A FAMILY OF STRUCTURALLY COMPLEX ANTIBIOTICS
  PRODUCED BY FERMENTATION WITH A STRAIN OF STREPTOMYCES AVERMITILIS
• IVERMECTIN IS ACTIVE IN LOW DOSAGE AGAINST A WIDE VARIETY OF NEMATODES AND
  ARTHROPODS THAT PARASITIZE ANIMALS
• STRUCTURE- PENTACYCLIC 16-MEMBERED–RING AGLYCONES GLYCOSIDICALLY LINKED AT
  THE 3-POSITION TO A DISACCHARIDE THAT COMPRISES TWO OLEANDROSE SUGAR
  RESIDUES
• SIDE CHAIN AT THE 25-POSITION OF THE AGLYCONE IS SEC-BUTYL IN AVERMECTIN B1A,
  WHEREAS IN AVERMECTIN B1B, IT IS ISOPROPYL


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AVERMECTINS B1A (-C2H5) AND B1B (-CH3)
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                               IVERMECTIN

• IVERMECTIN CONTAINS AT LEAST 80% OF 22,23-DIHYDROAVERMECTIN B1A AND
  NO MORE THAN 20% 22,23-DIHYDROAVERMECTIN B1B
• WIDESPREAD USE IN VETERINARY PRACTICE IN THE UNITED STATES AND MANY
  COUNTRIES THROUGHOUT THE WORLD FOR THE CONTROL OF ENDOPARASITES
  AND ECTOPARASITES IN DOMESTIC ANIMALS
• IT HAS BEEN FOUND EFFECTIVE FOR THE TREATMENT OF ONCHOCERCIASIS (“RIVER
  BLINDNESS”) IN HUMANS, AN IMPORTANT DISEASE CAUSED BY THE ROUNDWORM
  ONCOCERCA VOLVULUS
• MECHANISM- IT BLOCKS INTERNEURON–MOTOR NEURON TRANSMISSION IN
  NEMATODES BY STIMULATING THE RELEASE OF THE INHIBITORY NEUROTRANSMITTER
  GABA

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                   DIETHYLCARBAMAZINE CITRATE- SYNTHESIS




N, N-diethyl-4-methyl-1-piperazin   1-methylpiperazine
        Carbonyl chloride




                                                         Citric acid




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                 Nitration
                                    MEBENDAZOLE- SYNTHESIS                Reduction




4-chlorobenzophenone                                                            3,4-diaminobenzophenone




                                      methyl chloroformate
                 S-methylthiourea                            N-methoxycarbonyl-S-methylthiourea




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