Sem Lecture 2: January 27th

Treatment for Anti-mycobacterial drugs includes:

Rifampin, Isoniazid, Pyrazinamide, Ethambutol for 2 months
Then, Isoniazid and Rifampin for another 4 months

Mycobacteria have a very unique __________________
Are ________ Bacilli, are ________ growing.
Is Gram _____ (Sort of)

Cell envelop
Acid fast
Also slow growing
Positive

Mycobacteria have ___________

Mycolic Acids (C60-90)

Isoniazid is a _____________

pro-drug

Isoniazid is activated by _____________

KatG

The chemical intermediates that are activated by the Isoniazid prodrug chemically react with?

NADH cofactor

How do Isoniazid chemical intermediates react with NADH?

They react with C4 on the nicotinamide ring of the NADH cofactor
This adduct inhibits enoyl reductase

Blocking Enoyl Reductase prevents what?

Synthesis of Mycolic Acid

Why is the acetylation of Isoniazid via metabolism of great concern?

Acetylhydrazide is produced with is hepatotoxic (Acetylates liver proteins)

Rifampin MOA?
Napthalene ring interacts with what?

Inhibits bacterial RNA Polymerase.
aromatic amino acids in polymerase via pi-pi interactions

Aliphatic OH groups H-bond to _______________
Phenolic OH groups bind ______________

amino acids in polymerase
zinc in the polymerase

Primary Rifampin metabolite is _____________; still some _________
Rifampin is acid catylzed, so there is a loss of the _____________ Ring

deacetylated
activity
Piperazine

Rifapentine (Priftin) is much like Rifampin, but has a __________ added to the Piperazine

Cyclopentane

Pyrazinamide is a _________________ of nicotinamide

Bioisostere

MOA of Pyrazinamide?

Not known

Pyrazinamide is a ____________. Active form is ____________

Prodrug
pyrazinoic acid

Pyrazinamide lowers _________, which may contribute to the killing of mycobacterium.
Resistance occurs through mutation of ________

pncA (pyrazinadmidase)

Ethambutol MOA?

Disrupts synthesis of the arabinose and galactose region of the cell wall
Thought to mimic arabinose sugar, and blocks production of AG

Ethambutol weakens ___________; intracellular drugs can then get in (Rif)

cell wall

Streptomycin is one of the few aminoglycosides that can ____________.
Inhibits __________.
Metabolized by_______________________

penetrate the M. tb cell wall
protein synthesis
adding a phosphate or adenylate group to sugar -OH

Ethionamide (2nd line) inhibits _______________.

enoyl reductase

Cycloserine (2nd line) is an analog of _________. Blocks ______ linkage

D-Ala
Blocks D-Ala linkage

Fluoroquinolones work on a wide range of ____________ and _________ bacteria
Inhibits?

Gram +, Gram -
DNA Gyrase

Only _________ form of fluoroquinolones active against mycobacteria. Best ______ substituent for mycobacteria

fluorinated
C7

MAC (Mycobacterium avium-interacellulare complex) Treatment includes what?
_________ and _________ are ineffective

Ethambutol + Ciprofloxacin work well
INH, pyrazinamide

_____________ has been used since 1943 to treat leprosy

Dapsone

___________ are the major class that treats Leprosy
How do they work?

Diaryl sulfones
Blocks synthesis of folic acid

Sulfonamides are bacter_____. They inhibit _____________, competes w/___________ to block folate production.

static
dihydropteroate synthase
p-aminobenzoic acid

No folate means no __________ => No _____________

thymidine
DNA synthesis

sulfadiazine has a ___________. Used topically for __________.

Negatively charged Nitrogen in the Sulfonamide group which is stabilized by resonance.
Burns

Sulfisoxazole is a _________. Used in pediatric patients because?
Often used in combination with___________________

Prodrug
tasteless
Erythromycin

Sulfamethoxazole is used in combo with __________

Trimethoprim

Why is SMZ used with TMP?

The likelihood of a bacterium conferring resistance against both is very rare. Usually has to happen in two steps.

What is the latest TB drug to be created?
First drug to specifically target _________________

Sirturo (bedaquilin)
MDR M. tb

Sirturo has a black box warning considering?

Cardiovascular risk (arrhythmia possible)