4757 Melphalan 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. 148-82-3 460612 C13H18Cl2N2O2 White powder. 182.5°C < 0.1 g/100 mL at 22°C Incomplete, variable, 25-89% post oral dose Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases (primarily at the N-7 position of guanine and to a lesser extent, at the N-3 position of adenine), forming monoadducts and resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Melphalan is not actively metabolised, it spontaneously degrades to mono and dihydroxy products. Route of Elimination: The 24-hour urinary excretion of parent drug in these patients was 10% Њ± 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug. Half Life: 1.5 (&plusmn;0.83) hours LD₅₀=11.2 mg/kg (orally in rat) 1, carcinogenic to humans. (L135) 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. The principal toxic effect is bone marrow suppression. Vomiting, ulceration of the mouth, diarrhea, and hemorrhage of the gastrointestinal tract. 2014-09-11T02:05:38Z 2026-05-14T16:56:34Z http://en.wikipedia.org/wiki/Melphalan C07122 28876 DB01042 true N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O C13H18Cl2N2O2 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 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 305.2 304.074533244 Exogenous Solid -0.52 HMDB15176 CHEMBL852 405297 <p><a href="http://www.drugsyn.org/Melphalan.htm">DrugSyn.org</a></p> CHEM003660 DTXSID6020804 NS00068077 (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid 66.56 78.2315 31.383697992820657 8 4 2 1.2884430296765705 9.512487752295659 0 1 -0.22 -2.93 3.58e-01 g/l