M2011
Melphalan
powder
Synonym(s):
4-[Bis(2-chloroethyl)amino]-L-phenylalanine, L-PAM, L-Phenylalanine mustard
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About This Item
Empirical Formula (Hill Notation):
C13H18Cl2N2O2
CAS Number:
Molecular Weight:
305.20
UNSPSC Code:
12352207
NACRES:
NA.32
PubChem Substance ID:
EC Number:
205-726-3
Beilstein/REAXYS Number:
2816456
MDL number:
Form:
powder
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
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
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.
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signalword
Danger
hcodes
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
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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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
Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585.
Stuhmer T
British Journal of Haematology, 149(4), 529-536 (2010)