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Substance Name: Melphalan [USAN:USP:INN:BAN:JAN]
RN: 148-82-3
UNII: Q41OR9510P
InChIKey: SGDBTWWWUNNDEQ-LBPRGKRZSA-N

Note

  • 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.

Molecular Formula

  • C13-H18-Cl2-N2-O2

Molecular Weight

  • 305.2032
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Myeloablative Agonists
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1
  • Reportable Quantity (RQ) = 1 lb

Names and Synonyms

Name of Substance

  • Melphalan
  • Melphalan [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Melphalan

Synonyms

  • 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine
  • 3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine
  • 3025 C.B.
  • 4-(Bis(2-chloroethyl)amino)-L-phenylalanine
  • 4-14-00-01689 (Beilstein Handbook Reference)
  • Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-
  • Alkeran
  • AT-290
  • BRN 2816456
  • CB 3025
  • CCRIS 374
  • EINECS 205-726-3
  • Evomela
  • HSDB 3234
  • L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine
  • L-3-(para-(Bis(2-chloroethyl)amino)phenyl)alanine
  • L-PAM
  • L-Phenylalanine mustard
  • L-Phenylalanine, 4-(bis(2-chloroethyl)amino)-
  • L-Sarcolysin
  • L-Sarcolysine
  • L-Sarkolysin
  • Levofalan
  • Levofolan
  • Levopholan
  • Melfalan
  • Melfalano
  • Melfalano [INN-Spanish]
  • Melphalan
  • Melphalanum
  • Melphalanum [INN-Latin]
  • NCI-C04853
  • NSC 241286
  • NSC 8806
  • NSC-8806
  • p-Bis(beta-chloroethyl)aminophenylalanine
  • p-Di-(2-chloroethyl)amino-L-phenylalanine
  • p-L-Sarcolysin
  • p-N-Bis(2-chloroethyl)amino-L-phenylalanine
  • Phenylalanine mustard
  • Phenylalanine nitrogen mustard
  • RCRA waste number U150
  • SK 15673
  • UNII-Q41OR9510P

Systematic Names

  • Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-
  • L-Phenylalanine, 4-(bis(2-chloroethyl)amino)-
  • Melphalan

Superlist Names

  • L-Phenylalanine, 4-(bis(2-chloroethyl)amino)-
  • Melphalan
  • RCRA waste no. U150

Registry Numbers

CAS Registry Number

  • 148-82-3

FDA UNII

  • Q41OR9510P

Other Registry Number

  • 8057-25-8

System Generated Number

  • 0000148823

Structure Descriptors

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

Smiles

c1cc(ccc1C[C@@H](C(=O)O)N)N(CCCl)CCCl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo intravenous 4500mg/kg (4500mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: AGRANULOCYTOSIS
New Zealand Medical Journal. Vol. 97, Pg. 816, 1984.
dog LDLo intravenous 3mg/kg (3mg/kg) BLOOD: NORMOCYTIC ANEMIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
National Technical Information Service. Vol. PB88-133921,
human TDLo oral 1200ug/kg/5D- (1.2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 369, 1973.
human TDLo oral 700mg/kg/7D (700mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 367, 1969.
infant TDLo intravenous 28mg/kg (28mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: THROMBOCYTOPENIA

BLOOD: AGRANULOCYTOSIS
Lancet. Vol. 2, Pg. 1048, 1984.
man LDLo intravenous 8140mg/kg (8140mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

BLOOD: AGRANULOCYTOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
New Zealand Medical Journal. Vol. 97, Pg. 816, 1984.
mouse LD10 subcutaneous 32mg/kg (32mg/kg)   European Journal of Cancer. Vol. 10, Pg. 667, 1974.
mouse LD50 intravenous 20800ug/kg (20.8mg/kg) BLOOD: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
National Technical Information Service. Vol. PB88-133921,
mouse LD50 parenteral 6mg/kg (6mg/kg)   Cancer Research. Vol. 47, Pg. 62, 1987.
mouse LD50 unreported 29600ug/kg (29.6mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
rat LD50 intracrebral 200ug/kg (0.2mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966.
rat LD50 intraperitoneal 4484ug/kg (4.484mg/kg)   Biochemical Pharmacology. Vol. 13, Pg. 969, 1964.
rat LD50 intravenous 4100ug/kg (4.1mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 710, 1979.
rat LD50 oral 11200ug/kg (11.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 710, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 182.5 deg C   EXP
log P (octanol-water) -0.52 (none)   EXP
Water Solubility 45.7 mg/L 25 EST
Vapor Pressure 3.00E-10 mm Hg 25 EST
Henry's Law Constant 4.20E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.25E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.