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    Also known as: 3223-07-2, Melphalan hcl, Alkeran hydrochloride, Cb 3025 hydrochloride, Phenylalanine mustard hydrochloride, L-sarcolysine hydrochloride
    Molecular Formula
    C13H19Cl3N2O2
    Molecular Weight
    341.7  g/mol
    InChI Key
    OUUYBRCCFUEMLH-YDALLXLXSA-N
    FDA UNII
    1VXP4V453T
    Melphalan Hydrochloride
    Melphalan Hydrochloride is a bifunctional alkylating agent and phenylalanine derivative of nitrogen mustard. Melphalan hydrochloride is converted into highly reactive ethylenimmonium intermediates that induce covalent guanine N7-N7 intra- and inter-crosslinks and alkylation of adenine N3 of DNA. This agent also alkylates RNA and protein structures. As a result RNA transcription and protein synthesis are inhibited, ultimately leading to cell growth arrest and/or death.
    1 2D Structure

    Melphalan Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid;hydrochloride
    2.1.2 InChI
    InChI=1S/C13H18Cl2N2O2.ClH/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);1H/t12-;/m0./s1
    2.1.3 InChI Key
    OUUYBRCCFUEMLH-YDALLXLXSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC=C1CC(C(=O)O)N)N(CCCl)CCCl.Cl
    2.1.5 Isomeric SMILES
    C1=CC(=CC=C1C[C@@H](C(=O)O)N)N(CCCl)CCCl.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    1VXP4V453T
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 3223-07-2

    2. Melphalan Hcl

    3. Alkeran Hydrochloride

    4. Cb 3025 Hydrochloride

    5. Phenylalanine Mustard Hydrochloride

    6. L-sarcolysine Hydrochloride

    7. Sarcolysin Hydrochloride, L-

    8. Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, Monohydrochloride, L-

    9. 1vxp4v453t

    10. Cb-3025 Hydrochloride

    11. Evomela

    12. (2s)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic Acid;hydrochloride

    13. L-phenylalanine Mustard Hydrochloride

    14. 4-bis(2-chlorethyl)-amino-l-phenylalanine Hydrochloride

    15. Alanine Nitrogen Mustard

    16. Alkeran (tn)

    17. L-phenylalanine, 4-(bis(2-chloroethyl)amino)-, Monohydrochloride

    18. (s)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanoic Acid Hydrochloride

    19. Nsc8806

    20. Wln: Qvyz1r Dn2g2g &gh

    21. Evomela (tn)

    22. Melfalan Hydrochloride

    23. Alkeran (glaxosmith)

    24. L-alanine, Hydrochloride

    25. Unii-1vxp4v453t

    26. Schembl41335

    27. Chembl1200863

    28. Dtxsid60872785

    29. L-phenylalanine, Monohydrochloride

    30. Mfcd01674304

    31. Alanine Nitrogen Mustard Hydrochloride

    32. Akos025401785

    33. Melphalan Hydrochloride [vandf]

    34. Melphalan Hydrochloride [usp-rs]

    35. Melphalan Hydrochloride [who-dd]

    36. Ac-25549

    37. Ai3-26377

    38. Melphalan Hydrochloride [orange Book]

    39. D08173

    40. 223m072

    41. Q27252967

    42. 4-[bis(2-chloroethyl)-amino]-phenylalanine Hydrochloride

    43. 4-[bis(2-chloroethyl)-amino]-l-phenylalanine Hydrochloride

    44. L-3-(p-(bis(2-chloroethyl)amino)phenyl)alanine Monohydrochloride

    45. L-alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, Hydrochloride

    46. L-phenylalanine, 4-(bis(2-chloroethyl)amino)-, Hydrochloride (1:1)

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 341.7 g/mol
    Molecular Formula C13H19Cl3N2O2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count8
    Exact Mass340.051211 g/mol
    Monoisotopic Mass340.051211 g/mol
    Topological Polar Surface Area66.6 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity265
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    High-dose of Phelinun used alone or in combination with other cytotoxic medicinal products and/or total body irradiation is indicated in the treatment of:

    - multiple myeloma,

    - malignant lymphoma (Hodgkin, non-Hodgkin lymphoma),

    - acute lymphoblastic and myeloblastic leukemia,

    - childhood neuroblastoma,

    - ovarian cancer ,

    - mammary adenocarcinoma.

    Phelinun in combination with other cytotoxic medicinal products is indicated as reduced intensity conditioning (RIC) treatment prior to allogeneic haematopoietic stem cell transplantation (allo-HSCT) in malignant haematological diseases in adults.

    Phelinun in combination with other cytotoxic medicinal products is indicated as conditioning regimen prior to allogeneic haematopoietic stem cell transplantation in haematological diseases in the paediatric population as:

    - Myeloablative conditioning (MAC) treatment in case of malignant haematological diseases

    - RIC treatment in case of non-malignant haematological diseases.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L01AA03

    API Reference Price

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    12-May-2021
    03-Aug-2023
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