Melphalan

Melphalan
Clinical data
Trade namesAlkeran, Evomela, Phelinun, others
Other names(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
AHFS/Drugs.comMonograph
MedlinePlusa682220
License data
Routes of
administration		By mouth, intravenous, intra-arterial
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability25–89% (By mouth)
MetabolismHydrolysis to inactive metabolites
Elimination half-life1.5 ± 0.8 hours
ExcretionKidney (IV: 5.8–21.3%)
Identifiers
  • 4-[bis(2-Chloroethyl)amino]-L-phenylalanine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.207 Edit this at Wikidata
Chemical and physical data
FormulaC13H18Cl2N2O2
Molar mass305.20 g·mol−1
3D model (JSmol)
  • c1cc(ccc1C[C@@H](C(=O)O)N)N(CCCl)CCCl
  • 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 checkY
  • Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N checkY
  (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.[3][4][6][7] It is taken by mouth or by injection into a vein.[7]

Common side effects include nausea and bone marrow suppression.[7] Other severe side effects may include anaphylaxis and the development of other cancers.[7] Use during pregnancy may result in harm to the fetus.[8] Melphalan belongs to the class of nitrogen mustard alkylating agents.[7] It works by interfering with the creation of DNA and RNA.[7]

Melphalan was approved for medical use in the United States in 1964.[7] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[10]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ a b "Alkeran- melphalan tablet, film coated". DailyMed. 18 November 2019. Retrieved 23 April 2022.
  4. ^ a b Cite error: The named reference Evomela FDA label was invoked but never defined (see the help page).
  5. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/201848s000lbl.pdf [bare URL PDF]
  6. ^ a b Cite error: The named reference Phelinun EPAR was invoked but never defined (see the help page).
  7. ^ a b c d e f g "Melphalan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 9 October 2019.
  8. ^ "Melphalan Use During Pregnancy". Drugs.com. Retrieved 9 October 2019.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 873–874. ISBN 9780857113382.