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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
Form:
powder
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form

powder

Quality Level

200

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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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
0000514286
0000514286
0000145940
0000458779
0000458779

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Articles

DNA Damage and Repair

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.

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
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