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Prof. Patrick Davis Basic Medicinal Chemical Principles PHR 143M Fall-08
CH 2OH
CHO
COOH
O 1-THC PC=6000
C 2H 5
O C O
O HO OH
COO OH OH
Excreted Form O C 2H 5
CH2CH3 CH2CH3
C S
SH HS
C S
N (CH2)3 N
CH3 CH3
N (CH2)3 N
H CH3
Imipramine
Desipramine
N CH3 MPTP
+N CH3 MPDP
O O Warfarin (Anticoagulant)
N N H Azathioprine (Imuran)
N N H 6-Mercaptopurine (Toxic)
Allopurinol Colchicine Corticotropin Ibuprofen Prednisolone Prednisone Probenecid Sodium Thiosalicylate Sulfinpyrazone Triamcinolone
R = p-chlorophenyl
Links to endogenous, polar, ionizable cpd. Purpose: enhance excretion. Reaction types include:
O H N C CH3 O H N C CH3
O HN C CH3
NH2
Excretion
Liver
Stomach
Intestine
10
Significance?
regular drugs prodrugs See Foyes Table 8.13
How Overcome?
11
12