Functional Groups

Front 1

Alkanes

Back 1

C-C
Nonpolar, Hydrophobic, lipophilic.
Halothane is an alkane,
Halogen atom is cleaved in metabolism= oxidized carbon atoms.
P450 enzyme metabolism often.

Front 2

Alkenes

Back 2

C=C Hydrophobic.
Remember cis and trans stereochemestry, plays a moajro role in many drugs. Eg naloxone, vit K: trans,
Tamoxifen: Cis
Double bond is normally oxidized to form an epoxide.
Epoxides can permanently react with nucleophiles in DNA, RNA and amino acids.

Front 3

Alkynes

Back 3

Triple Bonded Carbons
Hydrophobic, no extensive metabolism.

Front 4

Aromatics

Back 4

Six Carbon ring with three shared double bonds. Found in Asparin, Nicotine, Diazapam. Metabolism resembles alkenes: epoxides form. Some water soluability

Front 5

Alcohols

Back 5

-OH (hydroxyl)
anything endind in -ol albuterol, propranolol, cholesterol. Soluable in H2O.
Metabolism 1 of 2 ways:
1.Oxidized to aldehydes, then carboxylic acids.
2. Conjugation with glucoronic acid or sulfuric acid (many drugs conjugate into glucuronides or sulfates ie Morphine 3-glucoruonide, Demerol.

Front 6

Phenols

Back 6

Arene ring with -OH
Acidic, very water soluable,
Ex morphine, estradiol, epi.
Metabolized by same conjugation as alcohols.

Front 7

Ethers

Back 7

C-O-C
increases soluability
Eg diphenhydramine, fluoxetine, doxepin.
diethylether among first volatile used. (Later became halogenated to give reduced side effects/ flamability)
Metabolized by hydroxylation of carbon atom which give hemiacetyl which quickly oxidizes to aldehydes or keytones, The remaining alcohol is metabolized.

Front 8

Thiols/thioesters

Back 8

C-S-H
"rotten eggs"
Metabolism resembles alchols: Conjugated to form glucoronides.

Front 9

Amines

Back 9

C-N--
(nitrogen bound to 3 or 4 atoms. Ammonia =NH3
Lipophilic, Basic, Primary secondary, tertiary, quatrernary lipophilicity and hydrophilicity(phobicity?) go up in this order.
Metabolism
1. P450 Monoamine oxidae (MAO)
2 multiple oxidation pathways yeilding dealkylated products.
3.N-oxydation and dealkylation yeilding sulfate formation. Sulfates are highly reactive ie MS metabolite almost as strong as parent compound.

Front 10

Aldehydes

Back 10

C-C=O

Front 11

Keytones

Back 11

key shape
increased water solubility
Methadone, corticosterone,
Metabolized by reduction of secondary alcohol, then catalyzed by aldo-keto-reductase, then conjugation of alcohol.

Front 12

Carboxylic acids

Back 12

Carbonyl-OH
Acidic, highly water souable,
Conjugation metabolism to Glucoronide
Naproxen ibuprofen ASA glutamate

Front 13

Esters

Back 13

Carbonyl-O-C

Cocain, ASA, Acetylcholine, Ester local anesthetics (one i)
Metabolysed by enzematic hydrolysis yeilding carboxylic acid and alcohol.
Esters have increeases lipophilicity.

Front 14

Amides

Back 14

Carbonyl carbon attached to nitrogen. More water soluable than esters.
Metabolism through hydrolysis and N-oxydation.
Eg PCN, All "amide" locals have two i's in the name. (amides are mor stable than ester locals due to slower hydrolysis)

Front 15

Sulfonamides

Back 15

Metabolized by oxidation
Quite acidic

Front 16

PKA

Back 16

The pH at which 50% of the molecules are ionized, and 50% are unionized.
ie HA<=>(A-) + (H+)

Front 17

Acid base Characteristics

Back 17

effects Water solubility: oral vs iv drugs.
Polar drugs are hydrophilic (oh and amines)
(alkanes and benzenes are lipophilic)