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Merck

M2011

Sigma-Aldrich

Melphalan

powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C13H18Cl2N2O2
Número de CAS:
Peso molecular:
305.20
Beilstein/REAXYS Number:
2816456
EC Number:
MDL number:
UNSPSC Code:
12352207
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.

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


Certificados de análisis (COA)

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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
Melphalan in the Treatment of Myelomatosis
Dorothy E. Speed
British Medical Journal, 1(5399), 1664-1669 (1964)
Use of the comet assay technique for quick and reliable prediction of in vitro response to chemotherapeutics in breast and colon cancer
Apostolou P
Journal of biological research (Thessalonike?, Greece), 21(1)14 (2014)
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
Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585.
Stuhmer T
British Journal of Haematology, 149(4), 529-536 (2010)

Artículos

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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