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148-82-3 molecular structure
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2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid

ChemBase ID: 914
Molecular Formular: C13H18Cl2N2O2
Molecular Mass: 305.20022
Monoisotopic Mass: 304.07453319
SMILES and InChIs

SMILES:
ClCCN(c1ccc(CC(N)C(=O)O)cc1)CCCl
Canonical SMILES:
ClCCN(c1ccc(cc1)CC(C(=O)O)N)CCCl
InChI:
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)
InChIKey:
SGDBTWWWUNNDEQ-UHFFFAOYSA-N

Cite this record

CBID:914 http://www.chembase.cn/molecule-914.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
IUPAC Traditional name
sarcolysin
Brand Name
Alkeran
L-PAM
L-Phenylalanine mustard
L-Sarcolysin
L-Sarcolysine
L-Sarkolysin
Levofalan
Melfalan
Mephalan
Phenylalanine mustard
Phenylalanine nitrogen mustard
Sarcolysine
Sarkolysin
Synonyms
4-[bis)2-Chloroethyl)amino-L-phenylalanine
Melphalan
CAS Number
148-82-3
EC Number
205-726-3
PubChem SID
160964377
PubChem CID
4053

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
MP Biomedicals
02155345 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.2884431  H Acceptors
H Donor LogD (pH = 5.5) 0.25192413 
LogD (pH = 7.4) 0.2493237  Log P 0.25219622 
Molar Refractivity 78.2315 cm3 Polarizability 30.09238 Å3
Polar Surface Area 66.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.22  LOG S -2.93 
Solubility (Water) 3.58e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
< 0.1 g/100 mL at 22°C expand Show data source
Melting Point
175-185°C expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
Storage Condition
Room Temperature (15-30°C), Protect from light expand Show data source
RTECS
AY3675000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
II expand Show data source
Australian Hazchem
2XE expand Show data source
Risk Statements
R:28-45 expand Show data source
Safety Statements
S:28-36/37/39-45-53 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank
MP Biomedicals - 02155345 external link
(4-[bis)2-Chloroethyl)amino-L-phenylalanine) Purity: 95% Light yellow powder.
DrugBank - DB01042 external link
Item Information
Drug Groups approved
Description 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. [PubChem]
Indication For the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. Has also been used alone or as part of various chemotherapeutic regimens as an adjunct to surgery in the treatment of breast cancer, alone or in combination regimens for palliative treatment of locally recurrent or unresectable in-transit metastatic melanoma of the extremities, as well as for the treatment of amyloidosis with prednisone.
Pharmacology Melphalan is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
Toxicity Vomiting, ulceration of the mouth, diarrhea, and hemorrhage of the gastrointestinal tract; The principal toxic effect is bone marrow suppression. LD50=11.2 mg/kg (orally in rat)
Affected Organisms
Humans and other mammals
Biotransformation Melphalan is not actively metabolised, it spontaneously degrades to mono and dihydroxy products.
Absorption Incomplete, variable, 25-89% post oral dose
Half Life 1.5 (±0.83) hours
Protein Binding Moderate to high (60 to 90%), primarily to albumin and, to a lesser extent, alpha 1-acid glycoprotein. 30% is irreversibly bound.
Elimination The 24-hour urinary excretion of parent drug in these patients was 10% ± 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug.
Distribution * 0.5 L/kg
References
Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. Epub 2008 Feb 14. [Pubmed]
Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. Pubmed
  • • Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. Epub 2008 Feb 14. Pubmed
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PATENTS

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