PHOrgChem (Lecture) | Module 9 (PART 4: COMMON DRUGS OF CARBOXYLIC ACID, ESTER, AMIDE, ACID ANHYDRIDE, ACID HALIDE, and THIOESTER)

Aspirin, Ibuprofen, Furosemide, and Naproxen

Drugs containing CARBOXYLIC ACIDS

Carboxylic Acid

Functional Group in ASPIRIN

Asprin

Use of Drug: Pain reliever, anti-inflammatory

Aspirin

Effect of Functional Group: Carboxylic acid allows COX enzyme binding but can lead to gastric irritation and is prone to hydrolysis

Carboxylic Acid

Functional Group in IBUPROFEN

Ibuprofen

Use of Drug: NSAID for pain and inflammation

Ibuprofen

Effect of Functional Group: Carboxylic acid enables strong ionic interaction with enzymes but may reduce membrane permeability

Carboxylic Acid

Functional Group in FUROSEMIDE

Furosemide

Use of Drug: Diuretic

Furosemide

Effect of Functional Group: Carboxylic acid improves kidney targeting and receptor binding, though it limits oral bioavailability

Carboxylic Acid

Functional Group in NAPROXEN

Naproxen

Use of Drug: Anti-inflammatory analgesic

Naproxen

Effect of Functional Group: Carboxylic acid group enhances COX inhibition but can undergo metabolic conjugation.

Enalapril, Oseltamivir, Cocaine, and Atorvastatin

Drugs containing ESTERS

Ester

Functional Group in ENALAPRIL

Enalapril

Use of Drug: ACE inhibitor (prodrug) for hypertension

Enalapril

Effect of Functional Group: Ester improves oral absorption and is hydrolyzed to the active carboxylic acid form in vivo.

Ester

Functional Group in OSELTAMIVIR

Oseltamivir

Use of Drug: Antiviral (influenza)

Oseltamivir

Effect of Functional Group: Ester group increases oral bioavailability and is enzymatically activated after absorption.

Tamiflu

Brand Name of Oseltamivir (ESTER-Containing Drug)

Ester

Functional Group in COCAINE

Cocaine

Use of Drug: Local anesthetic, CNS stimulant

Cocaine

Effect of Functional Group: Ester provides rapid metabolism by esterases, limiting duration of action.

Ester

Functional Group in ATORVASTATIN

Atorvastatin

Use of Drug: Cholesterol-lowering (statin)

Atorvastatin

Effect of Functional Group: Ester increases lipid solubility for absorption, then hydrolyzed to active acid form

Atorvastatin

Ester prodrug of active form

Acetaminophen, Lidocaine, and Diazepam

Drugs containing AMIDES

Amide

Functional Group in ACETAMINOPHEN

Acetaminophen

Use of Drug: Analgesic and antipyretic

Acetaminophen

Effect of Functional Group: Amide offers high stability and allows safe liver metabolism but limits water solubility

Amide

Functional Group in LIDOCAINE

Lidocaine

Use of Drug: Local anesthetic

Lidocaine

Effect of Functional Group: Amide group resists hydrolysis, increasing duration of action compared to ester anesthetics.

Amide

Functional Group in DIAZEPAM

Diazepam

Use of Drug: Anxiolytic, sedative

Diazepam

Effect of Functional Group: Amide enhances receptor affinity and metabolic stability in CNS applications.

Valium

Brand Name of Diazepam (AMIDE-Containing Drug)

Acid Halide

Functional Group in SULFUR MUSTARD

Sulfur Mustard

Use of Drug: Former chemical warfare agent

Sulfur Mustard

Effect of Functional Group: Acid halide group makes it extremely reactive, leading to DNA alkylation—unstable and toxic.

Acid Anhydride

Functional Group in ACETIC ANHYDRIDE

Acetic Anhydride

Use of Drug: Intermediate in drug synthesis (e.g., aspirin)

Acetic Anhydride

Effect of Functional Group: Highly reactive, useful for acetylation but chemically unstable in aqueous environments.

Acetyl-CoA, and Clopidogrel

Drugs containing THIOESTERS

Thioester

Functional Group in ACETYL-COA

Acetyl-CoA

Use of Drug: Metabolic intermediate, not a drug but critical for biosynthetic drug design

Acetyl-CoA

Effect of Functional Group: Thioester linkage is reactive and enables acyl group transfer; unstable but essential for function.

Thioester

Functional Group in CLOPIDOGREL

Plavix

Brand Name of Clopidogrel (THIOESTER-Containing Drug)

Clopidogrel

Use of Drug: Antiplatelet agent

Clopidogrel

Effect of Functional Group: Forms thioester intermediate during bioactivation; this functional group is crucial for irreversible receptor binding.