Melphalan
Title: Melphalan
CAS Registry Number: 148-82-3
CAS Name: 4-[Bis(2-chloroethyl)amino]-L-phenylalanine
Additional Names: p-di(2-chloroethyl)amino-L-phenylalanine; L-phenylalanine mustard; alanine nitrogen mustard; L-PAM; melfalan; L-sarcolysine
Manufacturers' Codes: NSC-8806; CB-3025
Trademarks: Alkeran (GSK); Sarcoclorin (Simes)
Molecular Formula: C13H18Cl2N2O2
Molecular Weight: 305.20
Percent Composition: C 51.16%, H 5.94%, Cl 23.23%, N 9.18%, O 10.48%
Literature References: Syntheses: Bergel, Stock, J. Chem. Soc. 1954, 2409; 1955, 1223; eidem, US 3032584; US 3032585 (both 1962 to NRDC); Larionov, Lancet 2, 169 (1955). Toxicity: W. C. J. Ross, Biochem. Pharmacol. 13, 969 (1964). Neurotoxicity study: M. G. Donelli et al., J. Pharm. Pharmacol. 18, 760 (1966). Mutation study: J. McCann et al., Proc. Natl. Acad. Sci. USA 72, 5135 (1975). Biliary excretion in rats: K. H. Byington et al., Biochem. Pharmacol. 29, 2518 (1980). Review of carcinogenicity studies: IARC Monographs 9, 167-180 (1975). Review: R. L. Furner, R. K. Brown, Cancer Treat. Rep. 64, 559-574 (1980).
Properties: Needles from methanol (monosolvate), mp 182-183° (dec). [a]D25 +7.5° (c = 1.33 in 1.0N HCl); [a]D22 -31.5° (c = 0.67 in methanol). Soluble in ethanol, propylene glycol. Practically insol in water. LD50 i.p. in rats: 14.7 mmol/kg (Ross).
Melting point: mp 182-183° (dec)
Optical Rotation: [a]D25 +7.5° (c = 1.33 in 1.0N HCl); [a]D22 -31.5° (c = 0.67 in methanol)
Toxicity data: LD50 i.p. in rats: 14.7 mmol/kg (Ross)
 
Derivative Type: D-Form
Additional Names: D-Sarcolysine; medphalan
Manufacturers' Codes: CB-3026; NSC-35051
Properties: Needles from methanol (monosolvate), mp 181.5-182° (dec). [a]D21 -7.5° (c = 1.26 in 1.0N HCl).
Melting point: mp 181.5-182° (dec)
Optical Rotation: [a]D21 -7.5° (c = 1.26 in 1.0N HCl)
 
Derivative Type: DL-Form
Additional Names: Merphalan; sarcolysine
Properties: Tiny needles from methanol, mp 180-181°.
Melting point: mp 180-181°
 
CAUTION: This substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-164.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrogen Mustards.

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