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Melphalan information


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
  • US DailyMed: Melphalan
Routes of
administration
By mouth, intravenous, intra-arterial
ATC code
  • L01AA03 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • US: WARNING[1]Rx-only[3][4][5]
  • EU: Rx-only[6]
Pharmacokinetic data
Bioavailability25–89% (By mouth)
MetabolismHydrolysis to inactive metabolites
Elimination half-life1.5 ± 0.8 hours
ExcretionKidney (IV: 5.8–21.3%)
Identifiers
IUPAC name
  • 4-[bis(2-Chloroethyl)amino]-L-phenylalanine
CAS Number
  • 148-82-3 checkY
PubChem CID
  • 460612
IUPHAR/BPS
  • 7620
DrugBank
  • DB01042 checkY
ChemSpider
  • 405297 checkY
UNII
  • Q41OR9510P
KEGG
  • D00369 checkY
ChEBI
  • CHEBI:28876 checkY
ChEMBL
  • ChEMBL852 checkY
CompTox Dashboard (EPA)
  • DTXSID6020804 Edit this at Wikidata
ECHA InfoCard100.005.207 Edit this at Wikidata
Chemical and physical data
FormulaC13H18Cl2N2O2
Molar mass305.20 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 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
  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.

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treatment for multiple myeloma in combination with dexamethasone or with melphalan and prednisone to treat acute episodes of erythema nodosum leprosum, as...

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transplantation. For these people, the standard of care has been chemotherapy with melphalan and prednisone. Recent studies among this population suggest improved...

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chemotherapy similar to that used in multiple myeloma. A combination of melphalan and dexamethasone has been found effective in those who are ineligible...

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[citation needed] Melphalan is a bifunctional alkylating agent frequently used in chemotherapy. Meiotic inter-strand DNA damages caused by melphalan can escape...

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Alkylating antineoplastic agent

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longer time than some of the other alkylating agents. Examples include melphalan and chlorambucil. The following three groups are almost always considered...

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bortezomib plus lenalidomide plus dexamethasone as well as bortezomib plus melphalan and prednisone may result in a large increase in the progression-free...

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IARC group 1 Carcinogens

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Fluoro-edenite fibrous amphibole Formaldehyde Gallium arsenide Lindane Melphalan Methoxsalen (8-Methoxypsoralen) plus ultraviolet A radiation 4...

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Administration (FDA) approved daratumumab for use in combination with bortezomib, melphalan and prednisone to include the treatment of people with newly diagnosed...

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Chemotherapy

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agents. Nitrogen mustards include mechlorethamine, cyclophosphamide, melphalan, chlorambucil, ifosfamide and busulfan. Nitrosoureas include N-Nitroso-N-methylurea...

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Lenalidomide

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received thalidomide or lenalidomide in conjunction with dexamethasone, melphalan, or doxorubicin. In March 2008, the US Food and Drug Administration (FDA)...

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Nitrogen mustard

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mustards developed include cyclophosphamide, chlorambucil, uramustine, melphalan, and bendamustine. Bendamustine has recently re-emerged as a viable chemotherapeutic...

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Cardiac amyloidosis

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abnormal cells that are producing them. Chemotherapeutic agents such as melphalan or bortezomib can be used to kill off the abnormal cell line that is producing...

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Spermatozoon

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spermatozoa-derived chromosomal aberrations. Treatment of male mice with melphalan, a bifunctional alkylating agent frequently employed in chemotherapy,...

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ATC code L01

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L01AA03 Melphalan L01AA05 Chlormethine L01AA06 Ifosfamide L01AA07 Trofosfamide L01AA08 Prednimustine L01AA09 Bendamustine L01AA10 Melphalan flufenamide...

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Sperm

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sperm cell-derived chromosomal aberrations. Treatment of male mice with melphalan, a bifunctional alkylating agent frequently employed in chemotherapy,...

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such as melphalan. Dosage regimens are selected on the basis of patient tolerance. Hematological response rates to the dexamethasone/melphalan regimens...

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Aspen Pharmacare

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from the United States. In 2009, Aspen purchased the rights to market Melphalan and several other cancer drugs from GSK, such as levothyroxine, azathioprine...

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Carmustine

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the recipient. Use under this protocol, usually with fludarabine and melphalan, was developed by oncologists at the University of Texas MD Anderson Cancer...

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history of exposure to chemotherapy (especially alkylating agents such as melphalan, cyclophosphamide, busulfan, and chlorambucil) or radiation (therapeutic...

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