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Melphalan Hydrochloride

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

INJECTABLE;INJECTION - EQ 50MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, POWDER;INTRAVENOUS - EQ 50MG BASE/VIAL

INJECTABLE;INJECTION - EQ 50MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
POWDER;INTRAVENOUS - EQ 50MG BASE/VIAL

RELATED EXCIPIENT COMPANIES

Suppliers, 1 Gangwal Chemicals

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1 Thickeners and Stabilizers, 1 Dry Powder Inhalation, 1 Parenteral, 1 Solubilizers, 1 Taste Masking, 1 Emulsifying Agents

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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 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 Formula	C₁₃H₁₉Cl₃N₂O₂
Molecular Weight	341.7 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Exact Mass	340.051211 g/mol
Monoisotopic Mass	340.051211 g/mol
Topological Polar Surface Area	66.6 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	265
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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