MELPHALAN

Synonyms. Melphalan; 4-(Bis(2-chloroethyl)amino)-L-phenylalanine; L-PAM; L-Phenylalanine mustard; p-Di(2-chloroethyl)amino-L-phenylalanine; Alanine nitrogen mustard; Melfalan; L-Sarcolysine; Alkeran; Sarcoclorin; 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine; Levofolan; Melphalanum; 3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine; L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine; L-3-(para-(Bis(2-chloroethyl)amino)phenyl)alanine; L-Sarkolysin; Levofalan; Melfalano;

MELPHALAN

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

148-82-3

EINECS RN

205-726-3

FORMULA

 C13H18Cl2N2O2

MOLE WEIGHT

305.20

H.S CODE

 2922.49.3700

SMILES

 c1(N(CCCl)CCCl)ccc(C[C@@H](C(=O)O)N)cc1

CLASSIFICATION

Alkylating agent, Antineoplastic agent, Nitrogen Mustard, Immunosuppressive agent, Myeloablative agonist

EXTRA NOTES

 An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen. (MeSH)
Overall Carcinogenic Evaluation: Group 1
Other RN: 8057-25-8

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white to off-white crystalline powder

MELTING POINT

182 ~ 183 C (Decomposes)

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Practically insoluble (46 mg/l)

SOLVENT SOLUBILITY Soluble in ethanol, propylene glycol

VAPOR DENSITY

 

log P(octanol-water)

 -0.52

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pK

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Melphalan

Google Scholar Search - Melphalan

Drug Information Portal (U.S. National Library of Medicine) - Melphalan

PubChem Compound Summary - Melphalan

Drug Bank -  Melphalan

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Melphalan

http://www.ebi.ac.uk/ - Melphalan

http://www.ncbi.nlm.nih.gov/ - Melphalan

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank - Melphalan

http://www.mims.com/
Mechanism of Action: Melphalan, a mechlorethamine derivative, is an alkylating antineoplastic agent. It forms carbonium ions, resulting in DNA and RNA synthesis inhibition. It cross-links DNA strands and acts on both resting and rapidly dividing tumour cells. Absorption: Variable absorption from the GI tract; absorption reduced by food (oral). Distribution: Rapid throughout body water. Protein-binding: 50-60%, mainly to albumin. Metabolism: Inactivated by hydrolysis. Excretion: Via urine (10%, as unchanged drug); 30-150 min (terminal half-life). MIMS Class: Cytotoxic Chemotherapy. ATC Classification: L01AA03 - Melphalan ; Belongs to the class of alkylating agents, nitrogen mustard analogues. Used in the treatment of cancer.

 

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98.5% min

MELTING POINT

182 ~ 183 C
IMPURITY

1.0% max (total), 0.5% max (individual)

LOSS ON DRYING

1.0% max

HEAVY METALS

20ppm max

OPTICAL ROTATION

+6.5°~ +8.5°(c = 1.26 in 1.0N HCl)

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

2811

HAZARD CLASS

 6.1
PACKING GROUP II

 

SAFETY INFORMATION

HAZARD OVERVIEW

Fatal if swallowed or in contact with skin. Causes mild skin irritation. Fatal if inhaled. May cause cancer. Suspected of damaging fertility or the unborn child. OSHA Hazards: Carcinogen, Highly toxic by inhalation, Highly toxic by ingestion, Highly toxic by skin absorption, Teratogen. Target Organs:Bone marrow, Reproductive system.

GHS

  

SIGNAL WORD

Danger

PICTOGRAMS

HAZARD STATEMENTS

H300-H310-H330-H350-H361

P STATEMENTS

P201-P260-P264-P280-P284-P302 + P350

EC DIRECTIVES

 

HAZARD CODES

T+

RISK PHRASES

45-46-61-25-36/37/38

SAFETY PHRASES

 53-26-37/39-45

 

PACKING