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Melphalan

Systematic (IUPAC) name
4-[bis(chloroethyl)amino]phenylalanine
Identifiers
CAS number	148-82-3
ATC code	L01AA03
PubChem	4053
DrugBank	APRD00118
Chemical data
Formula	C 13H18Cl2N2O2
Mol. mass	305.2 g/mol
Synonyms	2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid
Pharmacokinetic data
Bioavailability	25% to 89%
Metabolism	hydrolysis
Half life	1.5 ± 0.8 hours
Excretion	Renal, significantly metabolised
Therapeutic considerations
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral, intravenous
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Melphalan hydrochloride (trade name Alkeran) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents.

An alkylating agent adds an alkyl group (C_nH_2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring.

Otherwise known as L-Phenylalanine Mustard, or L-PAM, melphalan is a phenylalanine derivative of mechlorethamine.

Uses

It is used to treat multiple myeloma^[1] and ovarian cancer, and occasionally malignant melanoma.

The agent was first investigated as a possible drug for use in melanoma. It was not found to be effective, but has been found to be effective in the treatment of myeloma.

Administration

Oral or intravenous; dosing varies by purpose and route of administration as well as patient weight.

Side effects

Common side effects include:

• Nausea and vomiting, and oral ulceration.
• Bone marrow suppression, including
  • Decreased white blood cell count causing increased risk of infection
  • Decreased platelet count causing increased risk of bleeding

Less common side effects include:

• Severe allergic reactions
• Pulmonary fibrosis (scarring of lung tissue) including fatal outcomes (usually only with prolonged use)
• Hair loss
• Interstitial pneumonitis
• Rash
• Itching
• Irreversible bone marrow failure due to melphalan not being withdrawn early enough.
• Cardiac arrest.

References