Drug Table - Alkylating Agents Flashcards by Aqeel Nabijohn

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)

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Alkylating Agents Important Side Effects

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

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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)

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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)

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Mechlorethamine class

(Mustargen)

Nitrogen mustard

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Mechlorethamine mechanism

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

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Mechlorethamine Therapeutics

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

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Mechlorethamine “Other” side effects

Severe nausea and vomiting,
myelosuppression (leucopenia,
thrombocytopenia)

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Mechlorethamine Misc

Don’t use much anymore due to sterility

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Cyclophosphamide
(Cytoxan)
Class

Nitrogen mustard

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Cyclophosphamide
(Cytoxan)
Mechanism

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

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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

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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

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Cyclophosphamide
(Cytoxan)
“Other” Side Effects

Nausea, vomiting,

myelosuppression

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Cyclophosphamide
(Cytoxan)
Miscellaneous

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

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Difference between Ifosfamide and Cyclophosphamide

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

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Carmustine (Gliadel)
Lomustine (Ceenu)
Class

Nitrosoureas

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Carmustine (Gliadel)
Lomustine (Ceenu)
Mechanism

Alkylating agent

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Carmustine (Gliadel)
Lomustine (Ceenu)
Therapeutics

Brain tumors (cross blood-brain barrier)

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Carmustine (Gliadel)
Lomustine (Ceenu)
Imp Side Effects

Renal toxicity, pulmonary fibrosis

Carmustine (Gliadel)
Lomustine (Ceenu)
Other side effects

Profound myelosuppression,

severe nausea and vomiting

Dacarbazine (DTIC)

class

Triazenes

Dacarbazine (DTIC)

Mechanism

Alkylating agent; prodrug activated by liver

cytochromes

Dacarbazine (DTIC)

Therapeutics

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

Dacarbazine (DTIC) | "Other" Side Effects

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

Dacarbazine (DTIC) | Miscellaneous

IV administration

Procarbazine (Matulane) class

Triazenes

Procarbazine (Matulane) Mechanism

Alkylating agent; forms free radicals

Procarbazine (Matulane) Therapeutics

Hodgkin's lymphoma

Procarbazine (Matulane) Important side effects

May cause leukemia

Temozolomide (Temodar) class

Triazenes

Temozolomide (Temodar) Mechanism

Alkylating agent; nonenzymatic conversion | to methylhydrazine at physiologic pH

Temozolomide (Temodar) Therapeutics

Malignant gliomas

Temozolomide (Temodar) "Other" Side Effects

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

Temozolomide (Temodar) Miscellaneous

Taken orally

Cisplatin (Platinol) | class

Platinum analogs

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

Cisplatin (Platinol) | Therapeutics

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

Cisplatin (Platinol) | Imp Side Effects

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

Cisplatin (Platinol) | Other side effects

Severe nausea and vomiting, mild to moderate myelosuppression

Carboplatin (Paraplatin) Class

Platinum analogs

Carboplatin (Paraplatin) Mechanism

Carboplatin (Paraplatin) Therapeutics

Ovarian cancer

Carboplatin (Paraplatin) Other side effects

Myelosuppression | thrombocytopenia

Oxaliplatin (Eloxatin) | class

Platinum analogs

Oxaliplatin (Eloxatin) | Mechanism

Oxaliplatin (Eloxatin) | Therapeutics

Gastric and colorectal cancer

Oxaliplatin (Eloxatin) | Imp Side effects

Peripheral sensory neuropathy | cold-induced

Oxaliplatin (Eloxatin) | Other side effects

Neutropenia