Drug Metabolism in Drug Design and Development Basic Concepts and Practice

TABLE 11.1 (

Continued

)

Metabolic reaction

Description

Molecular formulachange

m

/z

change

R–COOH

!

R–CONHCH

COOH 2

Glycine conjugation

+C

H 2

NO 3

57.0215

R–OH

!

R–OSO

H 3

Sulfation

+SO

3

79.9568

R–H

!

R–OSO

H 3

Hydroxylation and

sulfation

+SO

4

95.9517

R–COOH

!

R–CONH–CH(CH

SH)–COOH 2

Cysteine conjugation

+C

H 3

NOS 5

103.0092

R–COOH

!

R–CONH–CH

CH 2

SO 2

H 3

Taurine conjugation

+C

H 2

NO 5

S 2

107.0041

R–CH

–R 2

0!

RR

0 –CH–SCH

CH(NH 2

)–COOH 2

S-Cysteine conjugation

+C

H 3

NO 5

S 2

119.0041

R–COOH

!

R–CO–SCH

CH(NHCOCH 2

)COOH 3

S,N

-Acetylcysteine

conjugation

+C

H 5

NO 7

S 2

145.0198

–CO + C

H 6

O 8

6

Decarboxylation and

glucuronidation

+C

H 5

O 8

5

148.0372

RR

0 –CH

! 2

RR

0 –CH–SCH

CH 2

(NHCOCH

)–COOH 3

N

-Acetylcysteineconjugation

+C

H 5

NO 7

S 3

161.0147

R–OH

!

R–O–C

H 6

11

O

5

Glucosidation

+C

H 6

10

O

5

162.0528

R–OH

!

R–O–C

H 6

O 9

6

Glucuronide conjugation

+C

H 6

O 8

6

176.0321

2

hydroxylation + 2

SO

3

2

hydroxylation + 2

sulfation

+S

O 2

8

191.9035

R–H

!

R–O–C

H 6

O 9

6

Hydroxylation +

glucuronide

+C

H 6

O 8

7

192.0270

334