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Merck

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:
148-82-3
Molecular Weight:
305.20
UNSPSC Code:
12352207
NACRES:
NA.32
PubChem Substance ID:
24278538
EC Number:
205-726-3
Beilstein/REAXYS Number:
2816456
MDL number:
MFCD00057717

Key Documents

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Product Name

Melphalan, powder

InChI key

SGDBTWWWUNNDEQ-LBPRGKRZSA-N

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

SMILES string

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

form

powder

color

white

Quality Level

200

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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.

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

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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Certificates of Analysis (COA)

Lot/Batch Number
059M4091V
088M4065V
127M4139V
019M4069V
106M4017V

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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)
Melphalan in the Treatment of Myelomatosis
Dorothy E. Speed
British Medical Journal, 1(5399), 1664-1669 (1964)
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
Marc G Stevenson et al.
Journal of surgical oncology, 117(7), 1447-1454 (2018-02-28)
This feasibility study presents the results of a new intensive treatment regimen for locally advanced extremity soft tissue sarcomas (ESTS), consisting of hyperthermic isolated limb perfusion (HILP), preoperative external beam radiotherapy (EBRT), and surgical resection. From 2011 to 2016, 11
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