Melphalan

Melphalan
Clinical data
Trade names	Alkeran, Evomela, Phelinun, others
Other names	(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a682220
License data	US DailyMed: Melphalan;
Routes of; administration	By mouth, intravenous, intra-arterial
ATC code	L01AA03 (WHO) ;
Legal status
Legal status	US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	25–89% (By mouth)
Metabolism	Hydrolysis to inactive metabolites
Elimination half-life	1.5 ± 0.8 hours
Excretion	Kidney (IV: 5.8–21.3%)
Identifiers
	IUPAC name 4-[bis(2-Chloroethyl)amino]-L-phenylalanine;
CAS Number	148-82-3 ;
PubChem CID	460612;
IUPHAR/BPS	7620;
DrugBank	DB01042 ;
ChemSpider	405297 ;
UNII	Q41OR9510P;
KEGG	D00369 ;
ChEBI	CHEBI:28876 ;
ChEMBL	ChEMBL852 ;
CompTox Dashboard (EPA)	DTXSID6020804 ;
ECHA InfoCard	100.005.207
Chemical and physical data
Formula	C13H18Cl2N2O2
Molar mass	305.20 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cc(ccc1C[C@@H](C(=O)O)N)N(CCCl)CCCl;
	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 ; Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N ;
	(verify)

Melphalan, sold under the brand name Alkeran among others, is a chemotherapy medication used to treat multiple myeloma; malignant lymphoma; lymphoblastic and myeloblastic leukemia; childhood neuroblastoma; ovarian cancer; mammary adenocarcinoma; and uveal melanoma. It is taken by mouth or by injection into a vein.

Common side effects include nausea and bone marrow suppression. Other severe side effects may include anaphylaxis and the development of other cancers. Use during pregnancy may result in harm to the fetus. Melphalan belongs to the class of nitrogen mustard alkylating agents. It works by interfering with the creation of DNA and RNA.

Melphalan was approved for medical use in the United States in 1964. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

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