3223-07-2

Basic information

• Product Name: 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE
• Synonyms: 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE;MELPHALAN HCL;MELPHALAN HYDROCHLORIDE;3-(p-(bis(2-chloroethyl)amino)phenyl)-,monohydrochloride,l-alanin;3-(p-(bis(2-chloroethyl)amino)phenyl)-l-alaninhydrochloride;4-(bis(2-chloroethyl)amino)-l-phenylalaninmonohydrochloride;alaninenitrogenmustardhydrochloride;l-3-(p-(bis(2-chloroethyl)amino)phenyl)alaninemonohydrochloride
• CAS NO: 3223-07-2
• Molecular Formula: C13H19Cl3N2O2
• Molecular Weight: 341.66
• EINECS: 205-726-3
• Mol File: 3223-07-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 175-178 °C
• Boiling Point: 473.1°Cat760mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 9.33E-10mmHg at 25°C
• CAS DataBase Reference: 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE(3223-07-2)
• EPA Substance Registry System: 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE(3223-07-2)

Safety Data

• Hazardous Substances Data: 3223-07-2(Hazardous Substances Data)

Usage

Uses

Melphalan Hydrochloride is used in combined intravitreal chemotherapy with topotecan hydrochloride for viable vitreous seeding from retinoblastoma. Also, it is an anti-cancer chemotherapy drug.

Safety Profile

Deadly poison by intravenousroute. Human systemic effects by ingestion: nausea andvomiting. Questionable carcinogen with experimentalcarcinogenic data. When heated to decomposition it emitsvery toxic fumes of Cl-, NOx, and HCl.

InChI:InChI=1/C13H18Cl2N2O2.ClH/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);1H/t12-;/m0./s1

Upstream product

• 148-82-3 L-PAM 
• 74743-23-0 N-phthalimido-4-amino-L-phenylalanine ethyl ester 
• 792864-20-1 N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester 
• 189744-28-3 N-(tert-butyloxycarbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine ethyl ester 
• 116366-27-9 (S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester 
• 17451-67-1 N-phthalimido-4-nitro-L-phenylalanine ethyl ester 

Relevant articles and documents

Proteoglycans as target for an innovative therapeutic approach in chondrosarcoma: Preclinical proof of concept

To date, surgery remains the only option for the treatment of chondrosarcoma, which is radio- and chemoresistant due in part to its large extracellular matrix (ECM) and poor vascularity. In case of unresectable locally advanced or metastatic diseases with a poor prognosis, improving the management of chondrosarcoma still remains a challenge. Our team developed an attractive approach of improvement of the therapeutic index of chemotherapy by targeting proteoglycan (PG)-rich tissues using a quaternary ammonium (QA) function conjugated to melphalan (Mel). First of all, we demonstrated the crucial role of the QA carrier for binding to aggrecan by surface plasmon resonance. In the orthotopic model of Swarm rat chondrosarcoma, an in vivo biodistribution study of Mel and its QA derivative (Mel-QA), radiolabeled with tritium, showed rapid radioactivity accumulation in healthy cartilaginous tissues and tumor after [3H]-Mel-QA injection. The higher T/M ratio of the QA derivative suggests some advantage of QA-active targeting of chondrosarcoma. The antitumoral effects were characterized by tumor volume assessment, in vivo 99mTc-NTP 15-5 scintigraphic imaging of PGs, 1H-HRMAS NMR spectroscopy, and histology. The conjugation of a QA function to Mel did not hamper its in vivo efficiency and strongly improved the tolerability of Mel leading to a significant decrease of side effects (hematologic analyses and body weight monitoring). Thus, QA conjugation leads to a significant improvement of the therapeutic index, which is essential in oncology and enable repeated cycles of chemotherapy in patients with chondrosarcoma.

Process for the Synthesis of Melphalan and the Hydrochloride Salt

The present invention relates to an improved process for the preparation of Melphalan, more specifically the invention relates to an efficient process for the preparation of substantially pure Melphalan hydrochloride (I).

An Improved Process for the Synthesis of Melphalan and the Hydrochloride Salt

The present invention relates to an improved process for the preparation of Melphalan, more specifically the invention relates to an efficient process for the preparation of substantially pure Melphalan hydrochloride (I).