PENICILLINS BETA LACTAM ANTIBIOTICS

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BETA LACTAM ANTIBIOTICS

PENICILLINS

PHARMACEUTICAL CHEMISTRY II

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PENICILLINS

Penicillin was discovered in

1928

by Scottish

scientist

Alexander Fleming,

who noticed that

one

of

his

experimental

cultures

of

staphylococcus

was contaminated with mold

(fortuitous accident)

, which caused the bacteria

to lyse. Since mold belonged to the family

Penicillium (Penicillium notatum), he named the

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PENICILLIN G

CHEMICAL STRUCTURE

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6-APA

• 6-APA is the chemical compound (+)-6-aminopenicillanic acid. • It is the core of penicillin.

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1 4 7 2 3 5 6

• 7-oxo-1- thia-4-azabicylo [3,2,0] heptane

PENAM RING

PENICILLANIC ACID

• 2,2–dimethyl penam –3– carboxylic acid

• 2,2-dimethyl-7-oxo-1- thia-4-azabicylo [3,2,0]heptane

-3-carboxylic acid

6-AMINO PENICILLANIC ACID (6-APA)

• 6-amino-2,2–dimethyl penam –3– carboxylic acid

• 6-amino-2,2-dimethyl-7-oxo-1- thia-4-azabicylo [3,2,0] heptane-3-carboxylic acid

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CH2 C O NH N S O COO-K+ CH3 CH3

PENISILLIN G (BENZYL PENICILLIN)

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N C H₂C H₂ O C₂H₅ C₂H₅ H C O N H₂ PENICILLIN G PROCAINE ‐

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H N C H₂C H₂ H N C H₂ C H₂ H H PENICILLIN G BENZATHINE ‐ ‐

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PHENETHICILLIN

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N S O COO-Na+ CH₃ CH₃ CONH OCH₃ OCH₃

6-[(2,6-dimethoxybenzoyl)amino] penicillanic acid sodium salt METHICILLIN SODIUM

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6-(2-ethoxy-1-naphtylcarbonylamino) penicillanic acid sodium salt NAFCILLIN SODIUM

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6-[(5-methyl-3-phenylizoxazole-4-yl)-carbonylamino] sodium penicillanate OXACILLIN SODIUM

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AMPICILLIN

( - Amino benzyl penicilin)

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AMOXICILLIN

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CARBENICILLIN DISODIUM

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CARBENICILLIN INDANYL SODIUM

6-[2-phenyl -2-(5-indanyloxycarbonyl) acetamino] penicillanic acid sodium salt

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TICARCILLIN DISODIUM

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β LACTAMASE ENZYME INHIBITORS

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AMOXICILLIN CLAVULANATE COMBINATION

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AMPICILLIN SULBACTAM COMBINATION

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PIPERACILLIN TAZOBACTAM COMBINATION

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IMIPENEM (CARBAPENEMS)

+

Cilastatin Imipenem

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