ANTIMETABOLI

TES
Prepared by:
Bati, Charrysse Bernadette
Cai, Delia Joyce
BSP3F

Definition
Antimetabolite

-a
substance that interferes
with the normal
metabolic processes
within cells, typically by
combining with enzymes.

Characteristics
Structural analogs of naturally
occurring compounds
Work via a variety of mechanisms
that include competitive inhibition
and incorporation into nucleic acids
S-phase-specific that interfere with
DNA synthesis
Myelosuppression is the dose
toxicity for all drugs in this class

Structure Activity
Relationship
5

1
2

Uracil

5Fluorouraci
l

1
2

5
6
7
4 9
3

Pteridine
ring

Para-amino
benzoic
acid

Glutamic
acid

Mechanism of Action

Classes of
Antimetabol
ites

Chemistry
Pyrimidine
These

drugs

drugs resemble
cytosine, thymine or uracil
Pyrimidine is a 6membered ring consisting
of four carbon atoms and
two nitrogen centers at
the 1- and 3- ring
positions

Pyrimidine drugs
Examples

Chemical Structure

Clinical Uses

5-Fluorouracil

Tx of several
carcinoma types
breast cancer,
stomach cancer,
pancreatic cancer,
Topical use basal cell
cancer of the skin

Floxuridine

Tx metastatic GI
adrenocarcinoma

Examples

Chemical Structure

Clinical Uses

Capecitabine

Tx breast cancer and

colorectal cancer

Gemcitabine

Tx of bladder cancer,
Pancreatic cancer,
And NSCLC (non-small
cell lung cancer)

Cytarabine

Tx of acute
myelogenous leukemia
and CML (Chronic
Myelogenous
Leukemia)

Examples

Chemical structure

Clinical Uses

Tegafur

is achemotherapeutic
fluorouracil prodrug
used in the treatment
of the ff cancers:
Stomach
Breast
Gallbladder
Lung
Colorectal
Head and neck
Liver
Pancreatic

Decitabine

for the treatment

ofmyelodysplastic
syndromes, a class of
conditions where
certain blood cells are
dysfunctional, and
foracute myeloid
leukemia

Chemistry
Purine

drugs
These drugs resemble
guanine or adenine. A
purine is a
heterocyclic aromatic
organic compound. It
consists of a
pyrimidine ring fused
to an imidazole ring

Purine Drugs
Examples

Chemical structure

Clinical Uses

6-Mercaptopurine

Tx of lymphoblastic
leukemia
Acute lymphocytic
leukemia
Crohns disease

Thioguanine

Tx acute
nonlymphocytic
leukemia

Cladribine

Used for Chronic

lymphocytic leukemia
Hairy cell leukemia
Non-Hodgkins
lymphoma

Examples

Chemical Structure

Clinical Uses

Pentostatin

For leukemias such

as: Hairy cell
leukemia,
Chronic lymphocytic
leukemia and
Lymphoblastic
leukemia

Fludarabine

Tx chronic
lymphocytic leukemia
and non-Hodgkins
lymphoma

Clofarabine

treat acute
lymphoblastic
leukemia in children
and young adults up
to 21 years old

Chemistry
Folates
Folate

is a general term for a group of water

soluble b-vitamins, and is also known as B9
compounds designed to interact at cofactor sites
for enzymes involved in the biosynthesis of
nucleic acid bases

Folate
drugs

Examples

Chemical structure

Clinical Uses

Methotrexate

Tx breast cancer
Bladder cancer
Colorectal cancer
Head and neck
cancer

Pemetrexed

Effective against
mesothelioma,
NSCLC, colorectal
cancer, bladder
cancer and lung
cancer

Trimetrexate

Tx colorectal cancer,
head and neck
cancer as well as
NSCLC

Adverse Effects