SYNTHETIC ANTIBAC PART 1 Flashcards by M.A.Lance Evangelista

best used as treatment for UTI caused by Eschericia coli.
should be polar

Quinolones

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basis of quinolones

Nalidixic Acid

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Highly polar quinolones enter through _____(these are the pores found in g(-) bacteria) into the cell

Porins

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may also antagonize GABA receptors in the brain (effect: CNS effects like tremor, sleep disorders, anxiety, convulsion)

Quinolones

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Designed mainly for g(-) bacteria

Quinolones

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a subgroup of quinolones because of the presence of 6-fluoro

Fluoroquinolones

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Quinolones

SAR
_____ (smaller the better) and ____ substitution at ______- better potency

Alkyl; Aryl; position 1

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_____ often times associated to crystalluria when urine is too BASIC also) and the ____ (C-6) constituent extends its activity

fluorine

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patients taking quinoles cannot be given __,___,___ or any divalent ions due to ___

Ca, Mg, antacids, chelation

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have moderate gram- negative activity and minimal systemic distribution

First generation

Cinoxacin (Cinoxacin)
nalidixic acid (NegGam,
Wintomylon)
oxolinic acid

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have expanded gram- negative activity and atypical pathogen coverage, but limited gram-positive activity

Second generation

Class I
Lomefloxacin (Maxaquin)
Norfloxacin (Noroxin)
Enoxacin (Penetrex)
Class II
Ofloxacin (Floxin)
Ciprofloxacin (Cipro) - FIRST LINE FOR UTI

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retain expanded gram-negative and atypical intracellular activity but have improved gram- positive coverage

3rd generation

Levofloxacin (Levaquin)
Sparfloxacin (Zagam)*
Moxifloxacin (Avelox)

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improve gram-positive coverage, maintain gram-negative coverage, and gain anaerobic coverage

Fourth generation

clinafloxacin
gemifloxacin (Factive)
moxifloxacin (Avelox, Vigamox)
Gatifloxacin (Tequin)
sitafloxacin
trovafloxacin (Trovan)
(withdrawn due to its toxicity)

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It interferes with DNA gyrase and inhibits DNA synthesis during bacterial replication

Nalidixic acid

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Active against gram (-) bacteria but not effective against pseudomonas organisms

Nalidixic acid

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Nalidixic acid active metabolite

7-hydroxymethyl metabolites

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It is a close congener of oxolinic acid, an antibacterial agent no longer in the market.

Cinoxacin

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It is more completely absorbed and less protein-bound than nalidixic acid

Cinoxacin

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Fluoride atoms provide an increase in potency against gram (+). Activity generally is not effective against obligate anaerobic bacteria. It is used for uncomplicated gonorrhea in 800 mg single oral dose

Norfloxacin

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The primary use is for the treatment of UTI and STD, for uncomplicated gonococcal urethritis and chancroid.

Enoxacin

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The bioavailability is reduced by divalent metal ions present in antacids and hematinics

Enoxacin

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Enoxacin is an enzyme inhibitor of

CYP 1A2

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has piperazine; can cause crystalluria

Enoxacin

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Best distribution among quinolones (CSF)

Ciprofloxacin

The drug is active against many anaerobes including Pseudomonas aeruginosa. This is used for treatment of UTI, lower respiratory infections, sinusitis, diarrhea, bone, joint & skin structure infection. It is used for gonococcal urethritis.

Ciprofloxacin

Agent of choice for bacterial gastroenteritis

Ciprofloxacin

It is incompatible with drugs that are alkaline

Ciprofloxacin

Food delays but does not prevent absorption.

Ciprofloxacin

For postexposure treatment of inhalational anthrax

Ciprofloxacin

Combination for gonococcal urethritis

Ciprofloxacin+ Doxycycline

Combination for disseminated gonorrhea

Ciprofloxacin + Ceftriaxone

Better than ciprofloxacin Not effective in syphilis

Ofloxacin

Although food can slow the oral absorptions of the lower respiratory tract, including chronic bronchitis and pneumonia, caused by Gram-negative bacilli

Ofloxacin

Supplied as a racemate

Ofloxacin

It is indicated for acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenza or Moraxella catarrhalis.

Lomefloxacin

The only quinolone for which once-daily oral dosing suffices

Lomefloxacin

C-8 with halogen causes Phototoxicity - most phototoxic

Lomefloxacin

With long elimination half-life, used for the treatment of bacterial gastroenteritis and cholecystitis. It shows the lowest incidence of phototoxicity.

Sparfloxacin

Sparfloxacin C-5: ____ portion decreases phototoxicity

Amino

Nitrofurans are derivatives of

5-nitro-2-furaldehyde

Nitrofurans SAR antimicrobial activity is present only when the ___ is in the _-position

nitro group; 5

Has a broad spectrum of activity against Gram-positive and Gram-negative bacteria but not Fungi

Nitrofurazone

0.2% usual concentration in solution, ointments and suppositories

Nitrofurazone

Full name of furazolidone

3'[(5-nitrofurylidene)amino]-2-oxazolidinone

It has bactericidal activity and also antiprotozoal activity, specifically against Giardia lamblia

Furazolidone

It can inhibit aldehyde dehydrogenase.

Furazolidone

It disrupts the bacterial enzyme system, active against gram (+) gram (-). It prevents and treats UTI. It colors the urine brown

Nitrofurantoin

To improve GI tolerance, the drug is designed using large crystalline form without interfering oral absorption

Nitrofurantoin

Methenamine's active agent

Formaldehyde

Methenamine requires acidifying agent like?

ammonium chloride, sodium biphosphate

It is employed internally as urinary antiseptic

Methenamine

It has the ability to furnish its own acidity. It is effective with smaller amounts of ___ acid and thus avoids the gastric disturbances

Methenamine mandelate; mandelic

Methenamine that does not need acidifying agent

Methenamine mandelate

Readily absorbed after oral administration and concentrated in the urinary bladder

Methenamine hippurate

local analgesic effect. It is given in combination with urinary antiseptics.

Phenazopyridine HCl

Phenazopyridine HCl + sulfisoxazole

Azo-Gantrisin

It gives an orange-red color stain.

Phenazopyridine HCl

is an acid-fast, aerobic bacteria with an unusual cell wall, containing a large percentage of lipid content.

M. Tuberculosis

is a synthetic antibacterial agent which is bactericidal against replicating organisms, but bacteriostatic against nonreplicating organisms.

Isonicotinic hydrazide/Isoniazid

Following exposure to INH, acid-fast bacilli lose their acid-fast characteristics, indicating that the agent interferes with?

Cell wall synthesis

The major metabolite of INH is

N-acetylisoniazid

prevents peripheral neuritis

Pyridoxine Vit B6

It is used in the treatment of isoniazid resistant tuberculosis or when the patient is intolerant to isoniazid and other drugs.

Ethionamide

Ethionamide blocks?

Mycolic acid synthesis

Pyrazinamide full name

Pyrazinecarboxamide (PZA)

Bioactivation of pyrazinamide to pyrazinoic acid by an ____ present in mycobacteria

amidase

PZA and its metabolites are reported to interfere with _____ excretion.

uric acid

is active only against dividing mycobacteria. (thus cannot be given alone)

Ethambutol

Ethambutol The ____ isomer is 16 times as active as the meso compound

dextro

Not recommended for use alone inhibits _________

Ethambutol; arabinosyl transferase

Diseases caused by ethambutol

Retrobulbar neuritis Green red color blindness

This agent was once quite popular, until significant resistance to the drug developed. It interferes with the incorporation of p. aminobenzoic acid into folic acid

P-AMINOSALICYLIC ACID

P-AMINOSALICYLIC ACID It interferes with the incorporation of

p. aminobenzoic acid into folic acid.

P-AMINOSALICYLIC ACID inhibits?

Folic acid synthesis

a basic red dye ("AZA") that exerts a slow, bactericidal effect on M. leprae. This is used in the treatment of leprosy, including the dapsone-resistant forms.

Clofazimine

This was also used for treating skin lesions cause by Mycobacterium ulcerans

Clofazimine

Source of rifampin

Streptomyces mediterranei

Rifampin binds to

bacterial DNA-dependent RNA polymerases

Most active agent in clinical use for the treatment of tuberculosis

Rifampin

The incidence of hepatotoxicity was significantly higher when rifampin was combined with ______

Isoniazid

Antitubercular Enzyme inducer

Rifampin

Orange to reddish brown crystalline powder

Rifampin

It is orally active against many Gram positive and Gram negative organisms, and is clinically effective against M. tuberculosis

Rifampin

greater potency against M. tuberculosis in vitro

Rifabutin

Despite its greater potency against M. tuberculosis in vitro, rifabutin is considered inferior to rifampin for the short-term therapy of tuberculosis because of its significantly ?

Lower plasma concentrations

This natural product cycloserine was isolated from _______ as the D __-isomer.

Streptomyces orchidaceus; D

Interestingly, the L-isomer is also active, and the racemic mixture is more potent than either isomer.

Cycloserine

In ____ form, cycloserine is sterically and stereochemically analogous to D alanine.

enolic

This antibiotic is a mixture of four cyclic polypeptides, where ______ 1a and 1b makes up 90% of the mixture.

capreomycin

thought to inhibit protein synthesis by binding to the 70s ribosomal unit. inhibits protein synthesis aminoglycosides

Capreomycin

intramuscular administration Resistance to sensitization dermatitis-wear gloves

Streptomycin

Binds to 12s and inhibits protein synthesis

Streptomycin