Fundamentals of Medicinal Chemistry

A.8 Prostaglandins

The prostaglandins are a group of naturally occurring compounds whose

molecular structures are based on that of prostanoic acid.

H

CH 3

H

COOH

10 8

9 7 5 3

624

1

(^111315)
12 14 16 18
17 19
20
Prostanoic acid

Prostaglandins are associated with the pathology of inflammation and fever.

They were believed to be synthesized in the prostate gland (hence the name) but

are now known to be synthesized throughout the body. A number of different

prostaglandins have been isolated and identified. They may be named using the

IUPAC system but are more commonly referred to by a series of abbreviations

that use PG to indicate a prostaglandin. These abbreviations are based on the

classification of the prostaglandins into families. The members of a family differ

only in the number, position and configuration of the alkene C¼C bonds in the

side chains and are distinguished by the use of a capital letter after PG (Figure

A8.1). Numerical subscripts following the final letter indicate the number and

configuration of the alkene double bonds that occur in the chains attached to

the five membered ring. An exception to this rule are the subscriptsaandb,

which are used to distinguish between the sub-groups of the PGF family based

on its 9aand 9bisomers respectively.

CH 3

CH 3

O

COOH

CH 3

COOH

CH 3

COOH COOH

OH

OH

PGA 1

PGB 1

H

H

H

H

O

HO

HO HO

HO HO

H PGF 2 α

H

H

H

H

O

H PGE 2

Figure A8.1 Examples of the structures and abbreviations used for prostaglandins

APPENDIX 8 PROSTAGLANDINS 255