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M2011

Sigma-Aldrich

Melphalan

powder

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Synonym(s):
4-[Bis(2-chloroethyl)amino]-L-phenylalanine, L-PAM, L-Phenylalanine mustard
Empirical Formula (Hill Notation):
C13H18Cl2N2O2
CAS Number:
Molecular Weight:
305.20
Beilstein/REAXYS Number:
2816456
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

form

powder

Quality Level

color

white

SMILES string

N[C@@H](Cc1ccc(cc1)N(CCCl)CCCl)C(O)=O

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

InChI key

SGDBTWWWUNNDEQ-LBPRGKRZSA-N

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1 of 4

This Item
359807338338BP391
vibrant-m

M2011

Melphalan

vibrant-m

359807

Z-Phe-OH

vibrant-m

338338

Fmoc-Phe-OH

vibrant-m

BP391

Melphalan

form

powder

form

-

form

-

form

-

color

white

color

-

color

-

color

-

General description

Melphalan also known as L-phenylalanine mustard is an alkylating agent. It belongs to the class of nitrogen mustards, which act as chemotherapeutic agents.

Application

Melphalan has been used as a drug along with HDAC-inhibitor JNJ-26481585 to treat multiple myeloma (MM) in cell lines and as a chemotherapeutic agent for breast cancer cell line.

Biochem/physiol Actions

In rat, melphalan in isolated lung perfusion (ILP) functions as a potent therapeutics for sarcomatous pulmonary metastases. It forms DNA intrastrand crosslinks by bifunctional alkylation in 5′-GGC sequences. Melphalan acts as a bone-marrow depressant and is implicated in the treatment of multiple myeloma and ovarian cancer.
Melphalan is an antineoplastic agent.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Carc. 1A - Muta. 1B - Repr. 2 - Skin Sens. 1

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585.
Stuhmer T
British Journal of Haematology, 149(4), 529-536 (2010)
G B Bauer et al.
Nucleic acids research, 25(6), 1211-1218 (1997-03-15)
Previous work showed that melphalan-induced mutations in the aprt gene of CHO cells are primarily transversions and occur preferentially at G-G-C sequences, which are potential sites for various bifunctional alkylations involving guanine N-7. To identify the DNA lesion(s) which may
Niels Wcj van de Donk et al.
The Lancet. Haematology, 5(10), e479-e492 (2018-10-07)
In patients with recently diagnosed multiple myeloma, the HOVON-50 phase 3 trial showed improved event-free survival for thalidomide-containing induction and maintenance regimens (in conjunction with high-dose melphalan and autologous stem cell transplantation [auto-SCT]) after a median of 52 months of
L Orlandi et al.
British journal of cancer, 74(12), 1924-1928 (1996-12-01)
We previously reported that combined treatment with melphalan and mild hyperthermia (1 h at 42 degrees C) caused a synergistic cytotoxic effect in JR8 melanoma cells, paralleled by a stabilisation of a melphalan-induced G2-phase cell block. In this study, we
Patrizia Falco et al.
Expert review of anticancer therapy, 7(7), 945-957 (2007-07-14)
Melphalan is an alkylating agent approved for the treatment of multiple myeloma and ovarian cancer. The combination of oral melphalan and prednisone was first introduced in the 1960s and remains the standard therapy for elderly multiple myeloma patients. High-dose melphalan

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

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