Drug Table - Alkylating Agents Flashcards Preview

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Flashcards in Drug Table - Alkylating Agents Deck (49)
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1

Alkylating Agents Mechanism

Produce strong electrophiles through
carbonium or ethyleneimonium ion
intermediates, which covalently bond via
alkylation of nucleophilic moieties in DNA
(mostly N7 position of guanine); Cell Cycle
Non-Specific (CCNS)

2

Alkylating Agents Important Side Effects

Bone marrow, mucosal toxicity,
nausea and vomiting, toxic effects
on reproductive systems,
increased leukemia risk

3

Alkylating Agents Miscellaneous

Resistance may occur due to:
decreased permeability or uptake;
increased rates of catabolism;
enhanced DNA repair; increased
glutathione production (inactivates
via conjugation)

4

List 11 Alkylating Agents

Mechlorethamine (Mustargen)
Cyclophosphamide (Cytoxan)
Ifosfamide (Ifex)
Carmustine (Gliadel)
Lomustine (Ceenu)
Dacarbazine (DTIC)
Procarbazine (Matulane)
Temozolomide (Temodar)
Cisplatin (Platinol)
Carboplatin (Paraplatin)
Oxaliplatin (Eloxatin)

5

Mechlorethamine class

(Mustargen)
Nitrogen mustard

6

Mechlorethamine mechanism

Alkylating agent; spontaneous conversion to active metabolites in body fluids or
enzymatically converted in liver

7

Mechlorethamine Therapeutics

Hodgkin's disease, topically for treatment of cutaneous T-cell lymphoma

8

Mechlorethamine "Other" side effects

Severe nausea and vomiting,
myelosuppression (leucopenia,
thrombocytopenia)

9

Mechlorethamine Misc

Don't use much anymore due to sterility

10

Cyclophosphamide
(Cytoxan)
Class

Nitrogen mustard

11

Cyclophosphamide
(Cytoxan)
Mechanism

Alkylating agent; conversion by hepatic cytochrome P450 to active metabolite phosphoramide mustard

12

Cyclophosphamide
(Cytoxan)
Therapeutics

Most widely used alkylating agent (broad clinical spectrum); singly or in
combination for ALL, CLL, non-Hodgkin's lymphoma, and breast, lung, and ovarian cancer

13

Cyclophosphamide
(Cytoxan)
Important Side Effects

Hemorrhagic cystitis (bladder
irritation) due to acrolein (toxic
drug metabolite); adequate
hydration and administration of
MESNA (2-mercaptoethane
sulfonate) minimizes problem

14

Cyclophosphamide
(Cytoxan)
"Other" Side Effects

Nausea, vomiting,
myelosuppression

15

Cyclophosphamide
(Cytoxan)
Miscellaneous

Relatively long plasma half-life (7-15 hrs); taken orally

16

Difference between Ifosfamide and Cyclophosphamide

Therapeutics
Ifos is used for Sarcoma and testicular cancer
Cyclophosphamide is the most widely used

17

Carmustine (Gliadel)
Lomustine (Ceenu)
Class

Nitrosoureas

18

Carmustine (Gliadel)
Lomustine (Ceenu)
Mechanism

Alkylating agent

19

Carmustine (Gliadel)
Lomustine (Ceenu)
Therapeutics

Brain tumors (cross blood-brain barrier)

20

Carmustine (Gliadel)
Lomustine (Ceenu)
Imp Side Effects

Renal toxicity, pulmonary fibrosis

21

Carmustine (Gliadel)
Lomustine (Ceenu)
Other side effects

Profound myelosuppression,
severe nausea and vomiting

22

Dacarbazine (DTIC)
class

Triazenes

23

Dacarbazine (DTIC)
Mechanism

Alkylating agent; prodrug activated by liver
cytochromes

24

Dacarbazine (DTIC)
Therapeutics

Part of ABVD for Hodgkin's disease; also, malignant melanoma

25

Dacarbazine (DTIC)
"Other" Side Effects

Nausea and vomiting,
myelosuppression (neutropenia, thrombocytopenia), flu-like
symptoms (fever, fatigue)

26

Dacarbazine (DTIC)
Miscellaneous

IV administration

27

Procarbazine
(Matulane)
class

Triazenes

28

Procarbazine
(Matulane)
Mechanism

Alkylating agent; forms free radicals

29

Procarbazine
(Matulane)
Therapeutics

Hodgkin's lymphoma

30

Procarbazine
(Matulane)
Important side effects

May cause leukemia

31

Temozolomide
(Temodar)
class

Triazenes

32

Temozolomide
(Temodar)
Mechanism

Alkylating agent; nonenzymatic conversion
to methylhydrazine at physiologic pH

33

Temozolomide
(Temodar)
Therapeutics

Malignant gliomas

34

Temozolomide
(Temodar)
"Other" Side Effects

Nausea and vomiting,
myelosuppression (neutropenia,
thrombocytopenia), flu-like
symptoms (fever, fatigue)

35

Temozolomide
(Temodar)
Miscellaneous

Taken orally

36

Cisplatin (Platinol)
class

Platinum analogs

37

Cisplatin (Platinol)
Mechanism

Alkylating agents that do not form
carbonium ion intermediates or formally
alkylate DNA; covalently bind nucleophilic
sites on DNA (e.g., guanine N7); converted
to active cytotoxic forms by reacting with
water to form (+)charged, hydrated
intermediates that react with DNA guanine,
forming inter- and intrastand cross-links

38

Cisplatin (Platinol)
Therapeutics

Testicular, ovarian, cervical, and
bladder cancers; also useful in
treatment of head and neck cancer,
and lung carcinoma

39

Cisplatin (Platinol)
Imp Side Effects

Nephrotoxicity, ototoxicity,
peripheral motor and sensory
neuropathy at high doses

40

Cisplatin (Platinol)
Other side effects

Severe nausea and vomiting,
mild to moderate
myelosuppression

41

Carboplatin
(Paraplatin)
Class

Platinum analogs

42

Carboplatin
(Paraplatin)
Mechanism

Alkylating agents that do not form
carbonium ion intermediates or formally
alkylate DNA; covalently bind nucleophilic
sites on DNA (e.g., guanine N7); converted
to active cytotoxic forms by reacting with
water to form (+)charged, hydrated
intermediates that react with DNA guanine,
forming inter- and intrastand cross-links

43

Carboplatin
(Paraplatin)
Therapeutics

Ovarian cancer

44

Carboplatin
(Paraplatin)
Other side effects

Myelosuppression
(thrombocytopenia)

45

Oxaliplatin (Eloxatin)
class

Platinum analogs

46

Oxaliplatin (Eloxatin)
Mechanism

Alkylating agents that do not form
carbonium ion intermediates or formally
alkylate DNA; covalently bind nucleophilic
sites on DNA (e.g., guanine N7); converted
to active cytotoxic forms by reacting with
water to form (+)charged, hydrated
intermediates that react with DNA guanine,
forming inter- and intrastand cross-links

47

Oxaliplatin (Eloxatin)
Therapeutics

Gastric and colorectal cancer

48

Oxaliplatin (Eloxatin)
Imp Side effects

Peripheral sensory neuropathy
(cold-induced)

49

Oxaliplatin (Eloxatin)
Other side effects

Neutropenia