Melphalan

Melphalan

Systematic (IUPAC) name
4-[bis(chloroethyl)amino]phenylalanine
Clinical data
Trade names	Alkeran
AHFS/Drugs.com	monograph
MedlinePlus	a682220
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral, intravenous
Pharmacokinetic data
Bioavailability	25% to 89%
Metabolism	hydrolysis
Half-life	1.5 ± 0.8 hours
Excretion	Renal, significantly metabolised
Identifiers
CAS number	148-82-3 Y
ATC code	L01AA03
PubChem	CID 4053
DrugBank	APRD00118
ChemSpider	405297 Y
UNII	Q41OR9510P Y
KEGG	D00369 Y
ChEBI	CHEBI:28876 Y
ChEMBL	CHEMBL852 Y
Synonyms	2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid
Chemical data
Formula	C13H18Cl2N2O2
Mol. mass	305.2 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1 Y Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N Y
N(what is this?)  (verify)

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 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.

Melphalan Prescribing Information: Alkeran

Melphalan Patient Information: MedlinePlus

Melphalan Material Safety Data Sheet (MSDS): Sequoia Research Products

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• Irreversible bone marrow failure due to melphalan not being withdrawn early enough.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.