Melphalan

Melphalan

Clinical data
Trade names	Alkeran
AHFS/Drugs.com	Monograph
MedlinePlus	a682220
Routes of administration	Oral (tablets), intravenous
ATC code	L01AA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	25–89% (oral)
Metabolism	Hydrolysis to inactive metabolites
Biological half-life	1.5 ± 0.8 hours
Excretion	Renal (IV: 5.8–21.3%)
Identifiers
IUPAC name 4-[bis(2-Chloroethyl)amino]-L-phenylalanine
Synonyms	(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
CAS Number	148-82-3 Y
PubChem CID	460612
IUPHAR/BPS	7620
DrugBank	DB01042 Y
ChemSpider	405297 Y
UNII	Q41OR9510P
KEGG	D00369 Y
ChEBI	CHEBI:28876 Y
ChEMBL	CHEMBL852 Y
ECHA InfoCard	100.005.207
Chemical and physical data
Formula	C13H18Cl2N2O2
Molar mass	305.2 g/mol
3D model (Jmol)	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 Y Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N Y

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 (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.

Melphalan chemically alters through alkylation of the DNA nucleotide guanine, and causes linkages between strands of DNA. This chemical alteration inhibits DNA synthesis and RNA synthesis, functions necessary for cells to survive. These changes cause cytotoxicity in both dividing and non-dividing tumor cells.

It is used to treat multiple myeloma,ovarian cancer, AL amyloidosis, and occasionally malignant melanoma.

The agent was first investigated as a possible drug for use in melanoma, it was not found to be effective.

On March 15, 2016 it was approved by the U.S. FDA under the trade name Evomela for:

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.