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Merck

M2011

Sigma-Aldrich

Melphalan

powder

Synonym(e):

4-[Bis-(2-chlorethyl)-amino]-L-phenylalanin, L-PAM, L-Phenylalanin-Mustard

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About This Item

Empirische Formel (Hill-System):
C13H18Cl2N2O2
CAS-Nummer:
Molekulargewicht:
305.20
Beilstein:
2816456
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352207
PubChem Substanz-ID:
NACRES:
NA.32

Form

powder

Qualitätsniveau

Farbe

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

InChIKey

SGDBTWWWUNNDEQ-LBPRGKRZSA-N

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Allgemeine Beschreibung

Melphalan also known as L-phenylalanine mustard is an alkylating agent. It belongs to the class of nitrogen mustards, which act as chemotherapeutic agents.

Anwendung

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. Wirkung

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.

Piktogramme

Skull and crossbonesHealth hazard

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 2 Oral - Carc. 1A - Muta. 1B - Repr. 2 - Skin Sens. 1

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585.
Stuhmer T
British Journal of Haematology, 149(4), 529-536 (2010)
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
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

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