Medicinal Chemistry Flashcards
Isomers
Non-identical molecules that have the same molecular formula.
Types: Constitutional and Stereoisomers.
Constitutional Isomers
Same molecular formula but different in constitution i.e. order of connectivity of atoms.
Stereoisomers
Same molecular formula and constitution but different in the arrangement of the atoms.
Enantiomers
They are stereoisomer compounds with the same connectivity but different arrangement of atoms in the space.
- one or more chiral center.
- non super-imposable mirror images.
- same physical and chemical properties.
- different to pharmacological actions.
Diastereomers
Stereoisomers not super-imposable and not mirror images. They have different physical and chemical properties. (Unlike Enantiomers)
Diastereomers can be optical isomers or geometric isomers.
Contain at least 2 chiral carbons.
Epimer
نفس الحاجة بظبط بس بيختلفوا في حاجة واحدة.
Glucose and Mannose (Epimer at C2)
Glucose and Galactose (Epimer at C4)
pKa
↑pKa ↑Basicity
↓pKa ↑Acidity
Log P
↑Log P ↑Lipophilicity
↓Log P ↑Hydrophilicity
Codeine Metabolism
Metabolized by CYP2D6—O-demethylation reaction at C3, converting 3-Methylmorphine (Codeine) into Morphine, the more potent analgesic.
*OXIDATION REACTION.
Ibuprofen (SAR)
- Methyl gp added to Ibufenac decreases hepatotoxicity and GI irritation.
- Isobutyl gp → maximum activity. Changing the number of carbons decreases the activity)
- Has one chiral center.
Why is Erythromycin sensitive to gastric pH?
Ketal formation between hydroxyl gp (6 and 12) and ketone at position 9.
Tricyclic Antidepressants (TCAs)
Potency: Tertiary > Secondary > Primary.
Secondary Amines are more selective towards NE transporters.
Tertiary Amines are non-selective towards serotonin and NE transporters.
Which TCA undergo photo-oxidation when exposed to light? (Photosensitive)
Clomipramine.
Anomer
Two sugars that differ in configuration only at the anomeric carbon i.e. the carbon bearing a hemiacetal)
