M2011

Sigma-Aldrich

Melphalan

powder

Synonym(s):
L-Phenylalanine mustard, 4-[Bis(2-chloroethyl)amino]-L-phenylalanine, L-PAM
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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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.

Packaging

1 g in glass bottle
100, 250 mg in glass bottle

Biochem/physiol Actions

Melphalan is an antineoplastic agent.
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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN2811 - class 6.1 - PG 2 - RQ - Toxic solids, organic, n.o.s. HI: all

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

S Nawata et al.
The Journal of thoracic and cardiovascular surgery, 112(6), 1542-1547 (1996-12-01)
Isolated lung perfusion allows the delivery of high-dose chemotherapy to the perfused lung and is an efficacious modality in the treatment of pulmonary metastases in the rat. Melphalan activity in this model was investigated. TOXICITY STUDY: Maximum tolerated dose of...
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...
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...
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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