Ciprofloxacin
Antibacterial agent, Fluroquinoline
synthetic product

Erythromycin
antibiotic (natural Product)
targets bacterial ribosomes
microlide

Quinine
malaria treatment
Natural product

Linezolid
antibacterial
attacking bacterial ribosomes
synthetic

Tetracycline
antibiotic
attacks bacterial ribosomes
natural product

Topotecan
Campothecin analog
anti-cancer drug

Lipitor
derived from fungus
synthetic
antihyperlipidemic

Getifinib
anti-cancer drug

Lovastatin
derived from fungus
Prodrug
Antihyperlipidemic

Taxol
anti-cancer agent

Morphine
natural product

Penicillin
Cell wall synthesis/inhibition
natural product

cephalosporin
Cell wall synthesis/inhibition

Heroin

Oyxcodone

Hydrocodone

Naloxone

Nalorphine

Methadone

Aspirin

Pyrrole

Pyrazole

Imidazole

Oxazole

Thiazole

Furan

thiophene

Pyridine

Pyrimidine

Indole

Benzofuran

Quinoline

Benzoimidazole

benzothiophene

Isoquinolline

Tautomerization

Xarelto
synthetic
blood thinner

Zofran

Camptothecin
natural product

Nexium
Proton pump inhibitor
synthetic drug

Bioisosteres -
ex: Tetrazole

Estrogen

pKa Phenol

Sulfonamide pKa

Imide pKa

pKa Aklylthiol

pKa Thiophenol

pKa N-Aryl Sulfonamide

pKa Sulfonimide

pKa Arylcarboxylic acid

pKa Sulfonic acid

pKa Aniline

pKa Pyridine

pKa Imine

pKa Amine

pKa Amidine

pKa Guanidine

Acid/Base Concentration Calculation

Carbon Solubility of different functional groups (mono-functional/poly-functional)

Water solubility based on partition coefficient

Synthroid
natural product

Zoloft
antidepressant
synthetic

Latuda
bipolar/depresion
synthetic

estrogen

Adderall

Zyrtec
allergy
synthetic

Effects on pKA and pH on weak acids and weak bases

Electron Donating group
(activating the ring)

Electron withdrawing group
(deactivating ring)

Halfordinol
anti-adipogenic activity, obesity

Amias
Benzimidazole Prodrug
angiotensin receptor antagonist for hypertension