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16746120
Sulphonamide Antibacterial Agent
Description
Lecture 1 Notes
No tags specified
chemistry
Mind Map by
Becky Harrison
, updated more than 1 year ago
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Created by
Becky Harrison
over 5 years ago
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Resource summary
Sulphonamide Antibacterial Agent
Drug Names
Code Name
Chemical Name
Generic/Non-Proprietary Name
Trade Name
Gram Test
Heteroaromatic purple stain mixed with bacteria
Sticks to outer membrane
Decolourisation with organic solvent
Gram Positive: Purple
Gram Negative: Red
Mode of Action
Prontosil
Azodye
Prodrug; reduced to sulphanilamide.
Prodrug
Compound metabolised in vivo to active form of drug.
SAR
Para-Amino essential (primary!)
Aromatic Ring and Sulphonamide essential
Sulphonamide primary or secondary only
R' only modifiable.
Improved Sulpha Drugs
Sulphanilamide
Poorly water soluble
Toxic via crystallisation in kidneys
Second Generation
Improved solubility via increased polarity
pKa close to that of most of the body.
Site of Action
Dihydropterase Synthase
Involved in folic acid biosynthesis
Folic Acid
Essential for 1-Carbon unit transport of all oxidation states.
Required for DNA synthesis.
Competitive Inhibitors
Sulphanilamide competes with PABA for dihydropterate synthase.
Bacterial DHFR different in structure than human's
Trimethoprim - competitive inhibitor of DHFR
Septrin
Synergistic
Trimethoprim and Sulphamethoxazole
Example of: Anti-metabolite and Bacteriostatic Drug
Media attachments
Sar (binary/octet-stream)
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