ANTI-PROTOZOAL - SULFONAMIDES Flashcards
- anaerobic, microaerophilic bacteria and protozoa
- “TRIAD OF FEATURES” which includes antiamebic, antigiardiasis, and antitrichomonal
METRONIDAZOLE
DOC for AMOEBA, GIARDIASIS / LABIASIS, TRICHOMONAL
METRONIDAZOLE
MOA:
* enters cell via CELL DIFFUSION
* NITROREDUCTION – similar with nitrofurans (produces FREE RADICALS)
* activated via single reduction step by bacteria → forms RADICALS → reacts with nucleic acid (by covalently binding the 5-nitro group to DNA) → cell death
METRONIDAZOLE
METRONIDAZOLE:
responsible for its stability in IV and tablet form
ethanoic moiety
- esters are to be ACTIVATED to exert amebicidal activity
- tx of asymptomatic carriers of E. histolytica
DILOXANIDE
- antibacterial and antifungal
- parent compound
8-hydroxyquinoline
- tx of ACUTE and CHRONIC INTESTINAL AMOEBIASIS
- AE: nueropathy
IODOQUINOL
IODOQUINOL:
adverse effect
neuropathy
- alkaloids obtained from IPECAC
- amoebicidal
- protoplasmic poison
- tx for LIVER disease since alkaloids concentrates mainly at the liver
- tx for BALANTIDIAL DYSENTERY and FLUKE infestations
EMETINE & DEHYDROEMETINE
- tx of PNEUMONIA caused by P. carinii
- tx for the prophylaxis of AFRICAN TRYPANOSOMIASIS
- tx for VISCERAL LEISHMANIAISIS
PENTAMIDINE ISETHIONATE
- highly RESISTANT to MALARIA
- highly LIPOPHILIC
- water INSOLUBLE analogue of ubiquinone 6
- tx of PCP caused by P. carinii (alternative)
- originally an antimalarial Plasmodium falciparum develops tolerance to its action
- high fat diet to improve absorption
ATOVAQUONE
- inhibitor of ORNITHINE DECARBOXYLASE
- tx of West African SLEEPING SICKNESS caused by T. gambiense
EFLORNITHINE
- NITROFURAN derivative
- tx of ACUTE and CHRONIC CHAGA’S disease (DOC)
NIFURTIMOX
- NITROIMIDAZOLE derivative as an alternative in the treatment of CHAGA’S disease
- SE: peripheral neuropathy, bone marrow suppression
BENZNIDAZOLE
BENZNIDAZOLE:
side effects
peripheral neuropathy
bone marrow supression
- DOC for later stages OF AFRICAN TRYPANOSOMIASIS
- excellent PENETRATION into the CNS
- causes ARSENIC toxicity
MELARSOPROL
MELARSOPROL:
adverse effect
arsenic toxicity
- pentavalent ANTIMONY-compound intended primarily for the tx of various LEISHMANIASIS (DOC)
- LOW TI
- should be monitored for heavy metal
SODIUM STIBOGLUCONATE
- HEAVY METAL POISON
- MOA: chelation
DIMERCAPROL
DIMERCAPROL:
MOA
chelation
- DOC for long term ____
- PROPHYLACTIC agent for AFRICAN TRYPANOSOMIASIS
SURAMIN SODIUM
- alternative for the treatment of Ascaris lumbcricoides and Enterobius vermicularis
- anticholinergic
- tx for PINWORM and ROUNDWORM
PIPERAZINE
PIPERAZINE MOA:
increase the ____ of the helminth muscle so that the muscle membrane is supressed leading to FLACCID PARALYSIS
resting potential
- SELECTIVE anthelmentic activity against FILARIASIS and ASCARIASIS
DIETHYLCARBAMAZEPINE CITRATE
- tx of PINWORMS and ASCARIS
- DEPOLARIZING NEUROMUSCULAR blocking agent
- ANTAGONIZE piperazine
PYRANTEL PAMOATE
PYRANTEL PAMOATE:
adverse effect
GI effect
PYRANTEL EMBONATEMOA:
promotes ____ of the helminth’s MYONERUAL JUNCTION and ____ → spastic paralysis and loss of muscle activity
depolarization
cholinesterase inhibition
- broad spectrum anthelmintic activity in human and livestock
- relive symptoms associated with CUTANEOUS LARVA MIGRANT and invasive phase of THRICOSIS
THIABENDAZOLE
- broad spectrum anthelmintic activity similar with thiabendazole
- MOA: inhibition of GLUCOSE UPTAKE leading to depleted glycogen storage → decrease ATP synthesis
- AE: abdominal discomfort and teratogenic
MEBENDAZOLE
MEBENDAZOLE MOA:
inhibition of ____ leading to depleted glycogen storage → decrease ATP synthesis
glucose uptake
MEBENDAZOLE:
adverse effects
abdominal discomfort
teratogenic
- broad spectrum anthelmentic activity against NEMATODES (intestinal)
- SINGLE-DOSE tx for ASCARIASIS, HOOKWORM, and TRICHURIASIS
- MULTIPLE DOSE therapy wfor the tx of PINWORM, THREADWORM, CAPILLARIASIS, CHLORNORCHIASIS, and HYDATID disease
HYDATID - seen in dogs
ALBENDAZOLE
ALBENDAZOLE:
____ for ASCARIASIS, HOOKWORM, and TRICHURIASIS
SINGLE DOSE
ALBENDAZOLE:
____ for the tx of PINWORM, THREADWORM, CAPILLARIASIS, CHLORNORCHIASIS, and HYDATID disease
MULTIPLE DOSE
- active against BLOOD TREMATODE: Shistosoma hematobium, S. japonicum, S. mansoni
- leads to BLOODY STOOL
NIRIDAZOLE
NIRIDAZOLE MOA:
inhibits the CONVERSION of the active form of ____ into inactive form
schistosomal glycogen phosphorylase
- TAENICIDE, a saline purge 1-2hrs after ingestion is recommended to REMOVE the SCOLEX and WORM SEGMENTS
- potent TAENICIDE that segments worms and scolex
NICLOSAMIDE
NICLOSAMIDE MOA:
inhibition of ____, ____ by ANaerobic metabolism and inhibition of ____ into ATP
inhibition of glucose uptake, energy production, inorganic phosphate incorporation
- CHLORINATED BISPHENOL formerly used in soaps and cosmetics for its antimicrobial activity
- Fasciolicide and Taenicide
BITHIONOL
- antischistosomial agent for INTESTINAL SCHISTOSOMIASIS
OXAMNIQUINE
OXAM sa HISTO
- broad spectrum against FLUKES
- DOC: BLOOD FLUKES
PRAZIQUANTEl
ZI QUAN pang DUGO
PRAZIQUANTEL MOA:
produces ____ contraction within the muscle system of the fluke (alteration in the influx of calcium ions) leading to segment worms
TETANIC-LIKE
- obtained from STREP. AVERMITILIS
- used in controlling ENDO and ECTO parasites in DOMESTIC ANIMALS
- effective for ONOCHOCERCIARIS in humans that is caused by Oncocerca volvulus
IVERMECTIN
DOC: NEMATODES
Ascaris lumbricoides
(roundworm)
PAM
Pyrantel palmoate
Albendazole
Mebendazole
DOC: NEMATODES
HOOKWORM
PAM
Pyrantel palmoate
Albendazole
Mebendazole
OLD-world hookworm
Anyclostoma duodenale
NEW-world hookworm
Necator americanus
DOC: NEMATODES
TRICHURIS
Trichuris trichuria
AM
Albendazole
Mebendazole
DOC: NEMATODES
STRONGYLOIDES
Ivermectin
STRONG si IVER
DOC: NEMATODES
Enterobius vermivularis
PM
Pyrantel palmoate
Mebendazole
PM mo si VERMI
DOC: NEMATODES
TRICHINELLA
Mebendazole
ELLA & BEN
DOC: NEMATODES
CUTANEOUS LARVA MIGRANS
AI
Albendazole
Ivermectin
nag MIGRATE si AIAI
DOC: NEMATODES
ONCHOCERCA VOLVULUS
Ivermectin
ECHOSERA si IVER
DOC: TREMATODES
Shistosoma haematobium
Schistosoma mansoni
Schistosoma japoniucm
Paragonimus westermani
PRAZIQUANTEL
nag SCHI (ski) at PARAgliding SI KWAN (ziquan)
DOC: TREMATODES
Fasciola hepatica
Bithionol
Triclalbendazole
may HEPA si no. 23
DOC: TREMATODES
Fasciolopsis buski
Praziquantel
Niclosamide
si AZI at NICO ay naglaro ng BUSKItbol
DOC: CESTODES
Taenia saginata
Taenia solium
Praziquantel
Niclosamide
kumain ng SAGing galing sa SOIL si AZI at NICO
DOC: CESTODES
Hymenolepsis nana
Niclosamide
kumain ng HYMEN si NICO
DOC: CESTODES
Cysticercosis
Albendazole
may CYST si ALBEN
DOC: CESTODES
Diphylobothrium latum
Praziquantel
Niclosamide
naglaro ng LATU LATU si AZI at NICO
DOC: CESTODES
Echinococcus granulosus
Albendazole
CHINO & ALBEN richards
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
compounds used to control MITES (Sarcoptes scabiei)
SCABICIDE
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
used to eliminate head, body, and crab LICE, FLEAS
PEDICULICIDE
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
- ester from PERU BALSAM
- topical scabicide
BENZOYL BENZOATE
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
BENZOYL BENZOATE:
components
benzyl alcohol
benzoyl chloride
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
- HALOGENATED HYDROCARBON with insecticidal activity
- a DIRECT POISON, fumigant effect, acts as a STOMACH POISON
- tx of SCABIES and PEDICULOSIS
LINDANE
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
TOPICAL tx of SCABIES
Crotamiton
ANTISCABIOUS AND ANTIPEDICULAR AGENTS
- synthetic PYRETHRINOID compound
- derived from permethrone
- exerts lethal action against LICE, TICKS, MITES, and FLEAS
- pediculicide fofr the treatment of HEADLICE
PERMETHRIN
ANTIBACTERIAL SULFONAMIDES
is SULFONAMIDES a TMP antibiotics?
TRIMETHOPRIN
NO
sulfonamides are SYNTHETIC antibacterial agents
ANTIBACTERIAL SULFONAMIDES
PARENT compound of SULFONAMIDES
PRONTOSIL
brilliant azo red dye
PRONTOSIL
NATURAL products biosynthesized by microorganisms that are toxic to toher species of microorganisms
ANTIBIOTICS
____ were the FIRST SUCCESSFUL SELECTIVELY TOXIC antibacterial drugs
SULFONAMIDES
SULFONAMIDES
____ was discovered by GERHARD DUGMAK in 1936
PRONTOSIL
SULFONAMIDES
PRONTOSIL was discovered by ____
GERHARD DUGMAK, 1936
SULFONAMIDES
- used to successfully treat PUERPERAL SEPSIS (childbirth fever) in London
- first effective CHEMOTHERAPEUTIC agent to cure bacterial infections in humans
PRONTOSIL
SULFONAMIDES
what reaction occurs in PRONTOSIL
azo reduction
SULFONAMIDES
PRODUCTS of PRONTOSIL AZO REDUCTION
Sulfanilamide + Triaminobenzene
SULFONAMIDES
- GERMAN bacteriologist and pathologist who was awarded the 1939 Nobel Prize for Physiology or Medicine for his discovery of the antibacterial effects of PRONTOSIL
GERHARD DOMAGK
SULFONAMIDES
the FIRST sulfonamide drugs
PRONTOSIL
SULFONAMIDES
- BRILLIANT AZO RED DYE
- found to protect against and cure Streptococcal infections in mice
- it is converted to its active metabolite “SULFANILAMIDE”
PRONTOSIL
SULFONAMIDES
PRONTOSIL:
active metabolite
sulfanilamide
SULFONAMIDES
- a generic term that denotes: ANILINE-substituted sulfonamides/sulfanilamides
- prodrugs that generate active sulfanilamides
SULFANILAMIDE
SULFONAMIDES
- NON-aniline sulfonamide
- used in BURN patients
- NONabsorbable
MAFENIE
trade name: Sulfamylon
SULFONAMIDES
Sulfonamides derived from p-amino-benzenesulfonamide are commonly referred to as ____
sulfa drugs
SULFONAMIDES
SULFA drugs are derived from
p-amino-benzenesulfonamide
SULFONAMIDES
era of sulfa drugs
1935
SULFONAMIDES | STRUCTURE
the chemical modification of this part of the molecule INCREASES ACTIVITY and modifies some pharmacological properties
R group
SULFONAMIDES | SARs
other aromatic rings or introducing other groups intro the benzene ring will ____ or ____ the ANTIMICROBIAL activities
decrease or lose
SULFONAMIDES | SARs
____ will enhance the POTENCY
MONO-substitution
SULFONAMIDES | SARs
____ have BETTER activities
HETEROCYCLIC rings
SULFONAMIDES | SARs
____ will LOSE their activities
BIS-substitution
SULFONAMIDES | SARs
____ are essential for antimicrobial activities
UNsubstituted or potential amino group
SULFONAMIDES | SARs
SULFONIC group must be in the ____ of ANILINE
4-position
SULFONAMIDES | SARs
____ or ____ substitution will LOSE the activities
2 or 4-position
SULFONAMIDES | SARs
____ wil DECREASE the potency
other amide group
SULFONAMIDES | SARs
- a sulfonamide that is a structural analog of PABA
- competitively INHIBITS the synthesis of DIHYDROFOLIC ACID from PABA
SULFAMETHOXAZOLE
SULFONAMIDES | SARs
- a structural analog of a portion of dihydrofolic acid
- competitively INHIBITS the synthesis of TETRAHYDROFOLIC acid
TRIMETHOPRIM
SULFONAMIDES | SARs
PRECURSORS of proteins, DNA, RNA
Tetrahydrofolic acid
SULFONAMIDES | SARs
STARTING molecules for the synthesis of folic acid
Para-aminobenzoic acid + Pteridine
SULFONAMIDES | SARs
SULFAMETHOXAZOLE and DAPSONE inhibits ____
DAPSONE - tx for LEPROSY
dihydroPTEROATE synthetase
SULFONAMIDES | SARs
TRIMETHOPRIM inhibits ____
dihydroFOLATE reductase
SULFONAMIDES | SARs
Sulfomethoxazole + Trimethoprim
CLOTRIMOXAZOLE
synergism
SULFONAMIDES | ABSORPTION
achieve PEAK blood levels in how many mins
30 mins
SULFONAMIDES | DISTRIBUTION
highly ____
plasma protein bound
SULFONAMIDES | DISTRIBUTION
Sulfonamides given in LATE TERM can INDUCE ____
neonatal jaundice
SULFONAMIDES | DISTRIBUTION
should NOT be taken with LARGE amounts of WATER to prevent ____
CRYSTALLURIA
SULFONAMIDES | TOXICITY
RENAL toxicity:
older sulfonamides
crystalluria
SULFONAMIDES | TOXICITY
BLOOD dyscrasias
hemolytic anemia
SULFONAMIDES | TOXICITY
DERMAL toxicity
rashes, pruritus, erythema, SJS
SULFONAMIDES | TOXICITY
RARE but serious SE
hepatitis
drug-induced fever
SULFONAMIDES | BACTERIAL RESISTANCE
synthesizing LARGE amounts of ____
PABA
SULFONAMIDES | BACTERIAL RESISTANCE
____ is altered so that it NO longer is inhibitable by sulfonamides
bacterial dihydropteroate synthetase
SULFONAMIDES | BACTERIAL RESISTANCE
bacteria utilize ____ which bypasses 1-carbon synthesis of bases
salvage pathway
SULFONAMIDES
spectrum of activity
G+, G-, Nocardia, Chlamydia, Protozoa, Enteric
SULFONAMIDES
ADR
CRANK
Crystalluria
Rashes
Anemia
Nausea
Kernicterus
SULFONAMIDES | ORAL ABSORBABLE SINGLE
antibacterial
Sulfamethizole
Sulfisoxazole
Sulfacetamide
Sulfachloropyridiazine
METH SOX ACET (asset) ni CHLORO
SULFONAMIDES | ORAL ABSORBABLE SINGLE
PRODRUG of Sulfisoxazole
Sulfisoxazole acetyl
SULFONAMIDES | ORAL ABSORBABLE SINGLE
- salt is prepared by adding enough DIETHANOLAMINE to a solution of SULFISOXAZOLE
- used in solution for SYSTEMIC administration
- used for installation of drops or ointments in the EYE for the treatment of LOCAL EYE INFECTION
SULFISOXAZOLE DIOLAMINE
SULFONAMIDES | ORAL ABSORBABLE SINGLE
SULFISOXAZOLE DIOLAMINE:
salt is prepared by adding enough ____ to a solution of sulfisoxazole
DIETHANOLAMINE
SULFONAMIDES | ORAL ABSORBABLE SINGLE
MORE SOLUBLE in ACIDIC urine
SULFAMETHAZINE
SULFONAMIDES | ORAL ABSORBABLE SINGLE
SULFAMETHAZINE:
more solbule in ____ urine
ACIDIC
SULFONAMIDES | ORAL ABSORBABLE SINGLE
FIRST agent for the treatment of PNEUMONIA
SULFAPYRIDINE
SULFONAMIDES | ORAL ABSORBABLE SINGLE
administered as a 5% solution in sterile water IV for patient requiring an immediate HIGH BLOOD LEVEL of SULFONAMIDE
Sulfadiazine sodium
SULFONAMIDES | ORAL ABSORBABLE MIX
- available in oral suspension and tablet form
- contains equal amount of sulfadiazine, sulfamerazine, sulfamethazine
TRIsulfapyrimidines
SULFONAMIDES | ORAL ABSORBABLE MIX
- tx of Plasmodium falciparum (px. with CHLOROQUINE resistance)
- useful for PROPHYLAXIS of chloroquine resistant P. falciparum malaria
- used for MALARIA PROPHYLAXIS for TRAVELLERS where chloroquine resistant malaria is ENDEMIC
Sulfadoxine & Pyrimethamine
SULFONAMIDES | TOPICAL
- VERY soluble in water
- used as EYE DROPS
- for REPEATED topical applications in the local management of OPHTHALMIC infections
Sulfacetamide sodium
SULFONAMIDES | TOPICAL
- SHORT to INTERMEDIATE acting sulfonamide
- IM, IV
Sulfisoxazole diolamine
SULFONAMIDES | TOPICAL
- contains sulfabenzamide, sulfacetamide, sulfathiozole
- as a VAGINAL cream in the tx of Haemophilus vaginalis
TRIsulfa
SULFONAMIDES | TOPICAL
TRIsulfa contains:
sulfabenzamide
sulfacetamide
sulfathiozole
nag TRI si BEN ng ACET niya kaya siya ay nakaTHIO
SULFONAMIDES | ORAL ABSORBABLE MIX
TRIsulfapyrimidines contains equal amounts of:
sulfadiazine
sulfamerazine
sulfamethazine
sina DIA, MERA at METHA ay gumawa ng PYRAMID
SULFONAMIDES | TOPICAL for BURN
- homologue of the sulfanilamide molecule that is NOT inhibited by PABA
- effective against Clostridium welchii and for the prophylaxis for wounds
Mafenide acetate
SULFONAMIDES | TOPICAL for BURN
- tx of infection against Pseudomonas spp.
- a VERY POTENT antimicrobial in the treatment of burns, scald, and wound infections
- PATIENT ACCEPTANCE is BETTER than mafenide
Silver sulfadiazine and zinc salt
SULFONAMIDES | TOPICAL for BURN
why is the PATIENT ACCEPTANCE of Silver sulfadiazine and zinc salt BETTER than MAFENIDE?
bc it does not cause systemic acidosis
SULFONILAMIDES | INTESTINAL, ULCERATIVE, BACTERIAL FLORA
- effectivev in treating ULCERATIVE COLITIS
Sulfasalazine
SULFONILAMIDES | INTESTINAL, ULCERATIVE, BACTERIAL FLORA
SULFASALAZINE:
prodrug
5-aminosalicylic acid & sulfapyridine
needed for BACTERIAL GROWTH and CELL DIVISION
Dihydrofolate Reductase inhibitors
DIHYDROFOLATE REDUCTASE INHIBITORS
- closely related to several anti-malarials
- a potent antibacterial
- tx of UNCOMPLICATED UTI
Trimethoprim
DIHYDROFOLATE REDUCTASE INHIBITORS
- tx of CHRONIC UTI
- DOC for booth COMPLICATED and UNCOMPLICATED UTI especially caused by ENTEROBACTERIA
Sulfamethoxazole & Trimethoprim
UNTOWARD EFFECTS OF SULFONAMIDES
HEMATOPOIETIC system
hemolytic anemia
(in G6PD deficient patients)
UNTOWARD EFFECTS OF SULFONAMIDES
URINARY tract
occlusions due to precipitates
UNTOWARD EFFECTS OF SULFONAMIDES
DRUG INTERACTION
high affinity to plasma proteins
Sulfonamides are used only when a particular agent is known to be ____ or ____ than other antibiotics for particular infeciton
equal or better
when sulfonamide is used SYSTEMICALLY:
____ and ____ must be monitored closely
hematopoietic system & renal function
when sulfonamide is used SYSTEMICALLY:
the patient must be given sufficient amount of water to produce ____ of urine
1.2 L / day
- reported to be effective against MALARIA and RICKETTSIAL infections
- MOA: same with sulfonamides
- CROSS RESISTANCE to sulfonamides
- mainly used for treating LEPROSY caused by M. leprae
SULFONES
SULFONES
reported to be effeective against ____ and ____ infections
malaria and rickettsial
SULFONES
MOA
same w sulfonamides
SULFONES
CROSS RESISTANCE to ____
sulfonamides
LEPROSY is also known as
Hansen’s disease
SULFONES
aside from rodents (mice) ____ is another biological test animal to culture M. leprae
ARMADILLO
SULFONES | DAPSONE STRUCTURE
susbtitution on both ____ and ____ functional groups
4- and 4’-amino
SULFONES | DAPSONE STRUCTURE
____ on ONLY ONE AMINO functional group
MONOsubstitution
SULFONES | DAPSONE STRUCTURE
____ on the BENZENOID RINGS
Nuclear substitution
SULFONES | DAPSONE STRUCTURE
replacement of ONE of the PHENYL ring with a ____
heterocyclic ring
SULFONES
DAPSONE:
parent compound
sulfone
SULFONES
PROTOTYPE of sulfone
DAPSONE
SULFONES
- treatment of both LEPROMATOUS and TUBERCULOID leprosy
- DOC: DERMATITIS HERPETIFORMIS
- sometimes used with pyrimethamine for the tx of MALARIA and with TMP for PCP
- SE: hemolytic anemia, methemoglobinemia, toxic hepatic effects
DAPSONE
SULFONES
DAPSONE:
DOC
dermatitis herpetiformis
SULFONES
DAPSONE:
sometimes used with ____ for the tx of MALARIA
pyrimethamine
SULFONES
DAPSONE:
sometimes used with ____ for PCP
Trimethoprim