Melphalan

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Melphalan
Melphalan.svg
Melphalan ball-and-stick.png
Systematic (IUPAC) name
4-[bis(chloroethyl)amino]phenylalanine
Clinical data
Trade names Alkeran
AHFS/Drugs.com monograph
MedlinePlus a682220
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 YesY
ATC code L01AA03
PubChem CID 4053
DrugBank DB01042
ChemSpider 405297 YesY
UNII Q41OR9510P YesY
KEGG D00369 YesY
ChEBI CHEBI:28876 YesY
ChEMBL CHEMBL852 YesY
Synonyms 2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid
Chemical data
Formula C13H18Cl2N2O2 
Mol. mass 305.2 g/mol
 YesY (what is this?)  (verify)

Melphalan (trade name Alkeran, in former USSR also known as Sarcolysin) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents.

An alkylating agent adds an alkyl group (CnH2n+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[edit]

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.

Melphalan is currently being used to treat ocular retinoblastoma, a pediatric solid tumor. This is accomplished via transarterial catheter based slow pulsed infusion into the ophthalmic artery.[2]

Administration[edit]

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

Melphalan Prescribing Information: Alkeran[3]

Melphalan Patient Information: MedlinePlus[4]

Melphalan Material Safety Data Sheet (MSDS): Sequoia Research Products[5]

Side effects[edit]

Common side effects include:

Less common side effects include:

References[edit]