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MEDICINAL ORGANIC CHEMISTRY > SYNTHETIC ANTIBACTERIALS > Flashcards

SYNTHETIC ANTIBACTERIALS Flashcards

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1
Q

Synthetic antibacterial agents are antibiotics.

True or False

A

False

Antibiotics are from natural origin.

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2
Q

QUINOLONES

Quinolones are patterned after ____, which is a ____ derivative.

A
  • Nalidixic acid
  • Naphthyridine
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3
Q

QUINOLONES

Prototype quinolone

A

Nalidixic Acid

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4
Q

QUINOLONES

Nalidixic Acid

Identify the isosteric heterocyclic grouping.

A

Napthyridines

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5
Q

QUINOLONES

Enoxacin

Identify the isosteric heterocyclic grouping.

A

Napthyridines

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6
Q

QUINOLONES

Cinoxacin

Identify the isosteric heterocyclic grouping.

A

Cinnolines

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7
Q

QUINOLONES

Norfloxacin

Identify the isosteric heterocyclic grouping.

A

Quinolones/Fluoroquinolones

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8
Q

QUINOLONES

Ciprofloxacin

Identify the isosteric heterocyclic grouping.

A

Quinolones/Fluoroquinolones

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9
Q

QUINOLONES

Ofloxacin

Identify the isosteric heterocyclic grouping.

A

Quinolones/Fluoroquinolones

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10
Q

QUINOLONES

Lomefloxacin

Identify the isosteric heterocyclic grouping.

A

Quinolones/Fluoroquinolones

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11
Q

QUINOLONES

Sparfloxacin

Identify the isosteric heterocyclic grouping.

A

Quinolones/Fluoroquinolones

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12
Q

QUINOLONES

Mechanism of action of quinolones

A
  1. DNA Topoisomerase IV inhibitor
  2. DNA gyrase inhibitor (TP II) -> Supercoiling -> -Cidal
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13
Q

QUINOLONES

Nalidixic Acid

Identify the generation.

A

1st

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14
Q

QUINOLONES

Cinoxacin

Identify the generation.

A

1st

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15
Q

QUINOLONES

Norfloxacin

Identify the generation.

A

2nd

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16
Q

QUINOLONES

Ciprofloxacin

Identify the generation.

A

2nd

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17
Q

QUINOLONES

Enoxacin

Identify the generation.

A

2nd

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18
Q

QUINOLONES

Ofloxacin

Identify the generation.

A

2nd

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19
Q

QUINOLONES

Levofloxacin

Identify the generation.

A

3rd

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20
Q

QUINOLONES

Sparfloxacin

Identify the generation.

A

3rd

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21
Q

QUINOLONES

Moxifloxacin

Identify the generation.

A

3rd

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22
Q

QUINOLONES

Gemifloxacin

Identify the generation.

A

3rd

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23
Q

QUINOLONES

Trovafloxacin

Identify the generation.

A

4th

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24
Q

QUINOLONES

  • Gram (-)
  • Not Pseudomonas species

Identify the generation based on the spectrum described.

A

1st

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25
Q

QUINOLONES

  • Gram (-) + Pseudomonas species
  • Gram (+) (S. aureus)
  • Atypical microorganisms

Identify the generation based on the spectrum described.

A

2nd

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26
Q

QUINOLONES

  • Gram (-) + Pseudomonas species
  • Extended Gram (+) and atypical microorganisms coverage

Identify the generation based on the spectrum described.

A

3rd

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27
Q

QUINOLONES

  • Gram (-) + Pseudomonas species
  • Extended Gram (+) and atypical microorganisms coverage
  • Broad anaerobic coverage

Identify the generation based on the spectrum described.

A

4th

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28
Q

QUINOLONES

Gastroenteritis caused by G. bacilli

A

Ciprofloxacin

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29
Q

QUINOLONES

This quinolone increases the effect of warfarin due to its enzyme inhibitor nature.

A

Ciprofloxacin

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30
Q

QUINOLONES

A quinolone that binds divalent cations, which decreases its absorption. Food also delays its absorption.

A

Ciprofloxacin

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31
Q

QUINOLONES

Ciprofloxacin is contraindicated with milk and ____ due to binding of divalent cations.

A
  1. Antacids
  2. Calcium supplements
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32
Q

QUINOLONES

This drug can lead to ruptured tendons in patients under 18 years old.

A

Moxifloxacin

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33
Q

QUINOLONES

The only quinolone that is taken once daily. It is the most phototoxic.

A

Lomefloxacin

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34
Q

NITROFURANS

First nitro heterocyclic compounds to be introduced into chemotherapy.

A

Nitrofurans

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35
Q

NITROFURANS

Nitrofurans are derivatives of ____, formed on reaction with the appropriate hydrazine or amine derivative.

A

5-nitro-2-furaldehyde

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36
Q

NITROFURANS

One of the earliest prototype nitrofurans

A

Nifurtimox

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37
Q

NITROFURANS

Tx of trypanosomiasis and leishmaniasis

A

Nifurtimox

Anti-protozoal

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38
Q

NITROFURANS

Adverse effects of nitrofurans

A

Mutagenic and Carcinogenic

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39
Q

NITROFURANS

Antimicrobial activity is present only when the nitro group is in the ____-position of Furan ring

A

5

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40
Q

NITROFURANS

Amebicide nitrofuran

A

Metronidazole

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41
Q

NITROFURANS

MOA: Reduction (nitrofuran reductase) of the nitro
group -> ____ (reactive intermediates) -> ____ damage -> inhibition of DNA, RNA, protein, and cell wall synthesis

A
  1. Free radicals
  2. Ribosomal proteins
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42
Q

NITROFURANS

The overall effect of nitrofurans to bacterial growth

A

Bactericidal

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43
Q

NITROFURANS

Topical tx of burns and prevention of bacterial infection associated with skin grafts

A

Nitrofurazone

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44
Q

NITROFURANS

Oral treatment of bacterial or protozoal diarrhea

A

Furazolidone

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45
Q

NITROFURANS

Nitrofuran that can inhibit aldehyde dehydrogenase

D/I: Alcohol

A

Furazolidone

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46
Q

NITROFURANS

Oral tx of UTI

A

Nitrofurantoin

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47
Q

NITROFURANS

Administered in a microcrystalline form to improve GI tolerance without inferring oral absorption

A

Nitrofurantoin

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48
Q

METHENAMINE & ITS SALTS

Methenamine is prepared by evaporating a solution of ____ and ____ to dryness.

A
  1. Formaldehyde
  2. Strong ammonia water
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49
Q

METHENAMINE & ITS SALTS

Methenamine is used for the treatment of ____.

A

Chronic UTI

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50
Q

METHENAMINE & ITS SALTS

To liberate the formaldehyde, the pH of the solution must be ____ (weakly acidic).

A

5.5

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51
Q

METHENAMINE & ITS SALTS

MOA: Liberation of ____ and enhanced by ____ with sodium bisphosphate or ammonium chloride

A
  1. Formaldehyde
  2. Acidifying
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52
Q

URINARY ANALGESIC

Former use: Urinary antiseptic
Current use: Urinary analgesic on the UT

A

Phenazopyridine HCl

Pyridium

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53
Q

URINARY ANALGESIC

Phenazopyridine HCl may tint the urine ____.

A

Red-orange

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54
Q

URINARY ANALGESIC

The stain by Phenazopyridine HCl may be removed by ____.

A

0.25% sodium dithionite

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55
Q

URINARY ANALGESIC

Phenazopyridine HCl is used in combination in ____ and ____.

A
  1. Azo-Gantrisin (+ Sulfisoxazole)
  2. Urobiotic (+ Oxytetracycline + Sulfamethizole)
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56
Q

ANTI-TUBERCULOSIS

Causative organism of tuberculosis

A

Mycobacterium tuberculosis

Koch Bacillus

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57
Q

ANTI-TUBERCULOSIS

Mycobacterium tuberculosis is a gram __ __ bacillus that live inside macrophages and lysosomes.

A

(+), acid-fast

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58
Q

ANTI-TUBERCULOSIS

Therapy for the management of TB

A

Shotgun Therapy

Use of multiple drug regimen

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59
Q

ANTI-TUBERCULOSIS

1st line single agent for TB

A

Streptomycin

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60
Q

ANTI-TUBERCULOSIS

1st line combination for TB

A
  1. Rifampicin
  2. Isoniazid
  3. Pyrazinamide
  4. Ethambutol

RIPE

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61
Q

ANTI-TUBERCULOSIS

MOA of rifampicin

A

RNA polymerase inhibitor

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62
Q

ANTI-TUBERCULOSIS

MOA of isoniazid

A

Mycolid acid inhibitor

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63
Q

ANTI-TUBERCULOSIS

MOA of pyrazinamide

A

Production of pyrazinoic acid -> low pH

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64
Q

ANTI-TUBERCULOSIS

MOA of streptomycin

A

30s ribosome inhibitor

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65
Q

ANTI-TUBERCULOSIS

MOA of ethambutol

A

Arabinogalactan synthesis and mycolic acid inhibition

Cell wall synthesis inhibition

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66
Q

ANTI-TUBERCULOSIS

Type of TB wherein the bacteria is resistant to 1-2 of the anti-TB drugs

Resistance to Isoniazid and Rifampin

A

Multidrug-resistant TB (MDR TB)

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67
Q

ANTI-TUBERCULOSIS

DOTS

A

Directly Observed Treatment Short-course

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68
Q

ANTI-TUBERCULOSIS

Type of TB wherein the bacteria is resistant to first-line and second-line anti-TB drugs

A

Extensively drug-resistant (XDR) TB

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69
Q

ANTI-TUBERCULOSIS

Recommended regimen for pulmonary TB that is virtually 100% effective but expensive

A

6-Month Regimen

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70
Q

ANTI-TUBERCULOSIS

Drugs included in the first two of 6-month TB regimen

A
  1. Rifampicin
  2. Isoniazid
  3. Pyrazinamide
  4. Ethambutol

RIPE

71
Q

ANTI-TUBERCULOSIS

Drugs included in the next 4 months of 6-month TB regimen

A
  1. Rifampicin
  2. Isoniazid
  3. Pyrazinamide

RIP

72
Q

ANTI-TUBERCULOSIS

Adverse effect of ethambutol

A

Retinobulbar Optic Neuritis

(Colorblindness)

73
Q

ANTI-TUBERCULOSIS

Rifampicin is produced by ____.

A

Streptomyces mediterranei

74
Q

ANTI-TUBERCULOSIS

The most active first line agent against TB

A

Rifampicin

75
Q

ANTI-TUBERCULOSIS

Rifampicin is an enzyme ____, which ____ the effect of paracetamol when taken concomitantly. This can lead to ____.

A
  1. Inducer
  2. Decreases
  3. Hepatotoxicity
76
Q

ANTI-TUBERCULOSIS

Rifampicin can tint the urine, stool, saliva, tears, and skin ____.

A

Red-orange

77
Q

ANTI-TUBERCULOSIS

1st choice for TB prophylaxis

A

Isoniazid

78
Q

ANTI-TUBERCULOSIS

2nd choice for TB prophylaxis

A

Rifampicin

79
Q

ANTI-TUBERCULOSIS

Safest, most potent and effective against all forms of M. tuberculosis

A

Isoniazid

80
Q

ANTI-TUBERCULOSIS

Adverse effects of isoniazid

A
  1. Hepatotoxicity
  2. Insomnia
  3. Peripheral Neuropathy

HIP

81
Q

ANTI-TUBERCULOSIS

Peripheral neuropathy associated with isoniazid can be managed by ____.

A

Vitamin B6 Pyridoxine

82
Q

ANTI-TUBERCULOSIS

1st line agent for short term TB

A

Pyrazinamide

83
Q

ANTI-TUBERCULOSIS

Synthetic analogue of Nicotinamide that penetrates inflamed meninges

A

Pyrazinamide

84
Q

ANTI-TUBERCULOSIS

Active against dividing mycobacteria

A

Ethambutol

85
Q

ANTI-TUBERCULOSIS

Basic red dye that exerts slow bactericidal effects on M. leprae

A

Clofazimine

86
Q

ANTI-TUBERCULOSIS

3 Secondary drugs treatment for TB

A
  1. Ethionamide
  2. Aminosalicylic Acid
  3. Aminosalicylate sodium
87
Q

ANTI-TUBERCULOSIS

Prophylaxis of disseminated MAC in AIDS patients

A

Rifabutin

88
Q

ANTI-TUBERCULOSIS

Isolated from S. orchidaceus, S. garyphalus, S. lavendulus

A

Cycloserine

89
Q

ANTI-TUBERCULOSIS

Strongly basic cyclic peptide (aminoglycoside) isolated from S. capreolus that is used as an alternative to streptomycin

A

Sterile capreomycin sulfate

90
Q

ANTI-TUBERCULOSIS

Adverse effect of rifampicin

A
  1. Cholestatic jaundice
  2. Renal toxicity
  3. Flu-like symptom
91
Q

ANTI-TUBERCULOSIS

Adverse effect of pyrazinamide

A
  1. Hepatotoxicity
  2. Hyperuricemia
92
Q

ANTIPROTOZOAL

Triad of features for metronidazole

A
  1. Trichomoniasis
  2. Amebiasis
  3. Giardiasis

TAG

93
Q

ANTIPROTOZOAL

Alternative for Vancomycin in the treatment of pseudomembranous colitis, anti-biotic induced diarrhea, and Clostridium difficile infection

A

Metronidazole

Flagyl

94
Q

ANTIPROTOZOAL

Tx of asymptomatic carriers of E. histolytica

A

Diloxanide

95
Q

ANTIPROTOZOAL

Parent compound that is an antibacterial and antifungal

A

8-Hydroxyquinoline

96
Q

ANTIPROTOZOAL

Tx of acute and chronic intestinal amebiasis

A

Iodoquinol

97
Q

ANTIPROTOZOAL

Adverse effect of iodoquinol

A

Neuropathy

Management: Vitamin B6 Pyridoxine

98
Q

ANTIPROTOZOAL

Tx of for balantidial dysentery, fluke infestations, and liver diseases

A

Emetine

From Ipecac

99
Q

ANTIPROTOZOAL

Tx for:
* P. carinii pneumonia
* African trypanosomiasis (Prophylaxis)
* Visceral leishmaniasis

PAV

A

Pentamidine isethionate

100
Q

ANTIPROTOZOAL

Originally an antimalarial drug, but Plasmodium falciparum developed tolerance

A

Atovaquone

101
Q

ANTIPROTOZOAL

Alternative to pentamidine isethionate for the treatment of P. carinii pneumonia (PCP)

A

Atovaquone

102
Q

ANTIPROTOZOAL

MOA of eflornithine

A

Ornithine decarboxylase inhibition

103
Q

ANTIPROTOZOAL

Tx of West African sleeping sickness, caused by Trypanosoma gambiense

A

Eflornithine

104
Q

ANTIPROTOZOAL

Drug of choice for acute and chronic Chaga’s disease

A

Nifurtimox

105
Q

ANTIPROTOZOAL

Alternative to nifurtimox for Chaga’s disease

A

Benznidazole

106
Q

ANTIPROTOZOAL

2 Adverse effects of benznidazole

A
  1. Peripheral neuropathy
  2. Bone marrow suppression
107
Q

ANTIPROTOZOAL

Drug of choice for later stages of African trypanosomiasis

A

Melarsoprol

108
Q

ANTIPROTOZOAL

Melarsoprol is known to cause ____ toxicity.

A

Arsenic

109
Q

ANTIPROTOZOAL

Drug of choice for various leishmaniasis

A

Sodium Stibogluconate

110
Q

ANTIPROTOZOAL

MOA of Dimercaprol

British Anti-Lewisite (BAL)

A

Chelation

111
Q

ANTIPROTOZOAL

Drug of choice for long term prophylactic agent for African trypanosomiasis

A

Suramin Sodium

112
Q

ANTHELMINTHICS

Platyhelminthes

A
  1. Tapeworms
  2. Flukes
113
Q

ANTHELMINTHICS

Nemathelminthes

A

Nematodes or true round worms

114
Q

ANTHELMINTHICS

Alternative treatment for pinworm (Enterobius vermicularis) and roundworm (Ascaris lumbricoides) infestations.

A

Piperazine

115
Q

ANTHELMINTHICS

Selective anthemintic activity against filariasis and ascariasis

A

Diethylcarbamazepine Citrate

116
Q

ANTHELMINTHICS

Depolarizing neuromuscular blocking agent for the treatment of pinworms and ascaris

spastic paralysis in susceptible helminths

A

Pyrantel Pamoate

117
Q

ANTHELMINTHICS

Pyrantel Pamoate has an antagonistic effect against ____.

A

Piperazine

118
Q

ANTHELMINTHICS

Broad-spectrum anthelmintic activity in human and livestock

A

Thiabendazole

119
Q

ANTHELMINTHICS

Broad-spectrum anthelmintic activity similar with thiabendazole

A

Mebendazole

120
Q

ANTHELMINTHICS

Broad-spectrum anthelmintic against intestinal nematodes

A

Albendazole

121
Q

ANTHELMINTHICS

Active against blood trematodes

A

Niridazole

122
Q

ANTHELMINTHICS

A potent taenicide; Saline purge 1 to 2 hours after ingestion to remove scolex and worm segments

A

Niclosamide

123
Q

ANTHELMINTHICS

  • Chlorinated bisphenol that is formerly used in soaps and cosmetics due to antimicrobial activity
  • Fasciolicide and taeniacide
A

Bithionol

124
Q

ANTHELMINTHICS

Tx of Schistosoma mansoni (intestinal schistosomiasis)

A

Oxamniquine

125
Q

ANTHELMINTHICS

MOA of praziquantel

A

Tetanic-like contraction of the fluke due alteration in the influx of calcium ions

126
Q

ANTHELMINTHICS

Drug of choice for blood flukes

A

Praziquantel

127
Q

ANTHELMINTHICS

Obtained from Streptomyces avermitilis

A

Ivermectin

128
Q

ANTHELMINTHICS

Controls endo and ecto parasites in domestic animals

A

Ivermectin

129
Q

ANTHELMINTHICS

Use of ivermectin in humans

A

Onchocerciasis (river blindness)

Oncocerca vovulus

130
Q

SCABICIDE AND PEDICULICIDE

Compounds used to control mites (Sarcoptes scabiei)

A

Scabicide

131
Q

SCABICIDE AND PEDICULICIDE

Used to eliminate head, body, crab lice, and fleas

A

Pediculicide

132
Q

SCABICIDE AND PEDICULICIDE

Benzyl alcohol + Benzoyl chloride

A

Benzoyl benzoate

133
Q

SCABICIDE AND PEDICULICIDE

Ester topical scabicide from peru balsam

A

Benzoyl benzoate

134
Q

SCABICIDE AND PEDICULICIDE

Halogenated hydrocarbon with insecticidal activity

A

Lindane

135
Q

SCABICIDE AND PEDICULICIDE

Direct contact poison: fumigant effect and acts as stomach poison

A

Lindane

136
Q

SCABICIDE AND PEDICULICIDE

Topical treatment for scabies that has an antipruritic effect and local anesthetic action

A

Crotamiton

Eurax

137
Q

SCABICIDE AND PEDICULICIDE

Lethal action against lice, ticks, mites, and fleas and pediculicide treatment of head lice

A

Permethrin

138
Q

SULFONAMIDES

Brilliant azo red dye which was found to protect against and cure Streptococcal infections in mice

A

Prontosil

139
Q

SULFONAMIDES

Active metablite of prontosil

A

Sulfanilamide

140
Q

SULFONAMIDES

Non-aniline sulfonamide

A

Mafenide Acetate

for burn therapy

141
Q

SULFONAMIDES

Sulfonamides are derived from ____.

A

p-amino-benzenesulfonamide

142
Q

SULFONAMIDES

MOA of sulfonamides

A

Dihydropteroate Synthetase inhibition

No DNA synthesis

143
Q

SULFONAMIDES

Mechanism of resistance of pathogen against sulfonamides

A

Increase production of PABA

144
Q

SULFONAMIDES

5 Adverse effects of sulfonamides

A
  1. Crystalluria
  2. Rashes
  3. Anemia
  4. Nausea
  5. Kernicterus

CRANK

145
Q

SULFONAMIDES: ORAL ABSORBABLE SINGLE

Prodrug of sulfisoxazole

A

Sulfisoxazole Acetyl

146
Q

SULFONAMIDES: ORAL ABSORBABLE SINGLE

Diethanolamine + Sulfisoxazole solution

A

Sulfisoxazole Diolamine

147
Q

SULFONAMIDES: ORAL ABSORBABLE SINGLE

More soluble in acidic urine

A

Sulfamethazine

148
Q

SULFONAMIDES: ORAL ABSORBABLE MIX

3 Components of trisulfapyrimidines

A
  1. Sulfadiazine
  2. Sulfamerazine
  3. Sulfamethazine
149
Q

SULFONAMIDES: ORAL ABSORBABLE SINGLE

First agent for the tx of pneumonia

A

Sulfapyridine

150
Q

SULFONAMIDES: ORAL ABSORBABLE MIX

Tx for pateints with malaria (Plasmodium falcifarum) and with chloroquine resistance

A

Sulfadoxine + Pyrimethamine

151
Q

SULFONAMIDES: ORAL ABSORBABLE MIX

Used for malaria prophylaxis for traveller’s where chloroquine resistant malaria is endemic

A

Sulfadoxine + Pyrimethamine

152
Q

SULFONAMIDES: TOPICAL

Used as eye drops in ophthalmic infections and very soluble in water

A

Sulfacetamide sodium

153
Q

SULFONAMIDES: TOPICAL

Short to intermediate acting sulfonamide IM, IV

A

Sulfisoxazole diolamine

154
Q

SULFONAMIDES: TOPICAL

3 Components of TriSulfa

A
  1. Sulfabenzamide
  2. Sulfacetamide
  3. Sulfathiozole
155
Q

SULFONAMIDES: TOPICAL

Vaginal cream for Haemophilus vaginalis

A

TriSulfa

156
Q

SULFONAMIDES: TOPICAL NON-ABSORBABLE

Non-absorbable topical sulfonamides are used for ____.

A

Burn Therapy

157
Q

SULFONAMIDES: TOPICAL NON-ABSORBABLE

Homologue of the sulfanilamide molecule that is not inhibited by PABA

A

Mafenide Acetate

SULFAMYLON

158
Q

SULFONAMIDES: TOPICAL NON-ABSORBABLE

Adverse effect of mafenide acetate (Sulfamylon)

A

Systemic Acidosis

159
Q

SULFONAMIDES: TOPICAL NON-ABSORBABLE

Tx of Pseudomonas spp. infections

A

Silver sulfadiazine + Zinc Salt

160
Q

SULFONAMIDES: TOPICAL NON-ABSORBABLE

Very potent antimicrobial for burns, scald, and wound infections with better patient acceptance than mafenide

A

Silver sulfadiazine + Zinc Salt

161
Q

SULFONAMIDES

Effective in treating ulcerative colitis

A

Sulfasalazine

Colon specific

162
Q

SULFONAMIDES

Sulfasalazine is a prodrug metabolized into ____ and ____.

A

p/m-aminosalicylic acid and
sulfapyridine

163
Q

DIHYDROFOLATE REDUCTASE INHIBITORS

For uncomplicated UTI

A

Trimethoprim

164
Q

DIHYDROFOLATE REDUCTASE INHIBITORS

Potent antibacterial that is closely related to several anti-malarials but does not have good antimalarial activity

A

Trimethoprim

165
Q

DIHYDROFOLATE REDUCTASE INHIBITORS

For chronic UTI and the drug of choice for complicated and uncomplicated UTI especially caused by entero-bacteria

A

Sulfamethoxazole + Trimethoprim

SMX + TMP = CO-TRIMOXAZOLE

166
Q

DIHYDROFOLATE REDUCTASE INHIBITORS

Co-trimoxazole is a combination of ____ and ____.

A

Sulfamethoxazole + Trimethoprim

SMX + TMP

167
Q

SULFONES

Sulfones are mainly used for treating ____ (Leprosy) caused by Mycobacterium leprae

A

Hansen’s Disease

168
Q

SULFONES

Test animals to culture M. Leprae.

A

Mice and Armadillo

169
Q

SULFONES

Parent sulfone and protype

A

Dapsone, DDS

Avlosulfone

170
Q

SULFONES

For both lepromatous and tuberculoid leprosy

A

Dapsone, DDS

Avlosulfone

171
Q

SULFONES

Dapsone is the drug of choice for ____.

A

Dermatitis Herpetiformis

172
Q

SULFONES

Dapsone is sometimes used with ____ for the tx of malaria with TMP for PCP.

A

Pyrimethamine

173
Q

SULFONES

Adverse effects of dapsone

A
  1. Hemolytic anemia (G6PCD)
  2. Methemoglobinemia
  3. Hepatotoxicity
174
Q

SULFONES

Reported to be effective against malaria and rickettsia infections

A

Sulfones

MEDICINAL ORGANIC CHEMISTRY (17 decks)

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