SARCOLYSIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H18Cl2N2O2
Molecular Weight	305.2
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O

InChI

InChIKey=SGDBTWWWUNNDEQ-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C13H18Cl2N2O2
Molecular Weight	305.2
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/014691s029lbl.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207155s000lbl.pdf

Sarcolysin is the isomeric form of melphalan with alkylating activity. Sarcolysin is a bifunctional alkylating agent. The cytotoxicity of sarcolysin appears to be related to the extent of its interstrand cross-linking with DNA, probably by binding at the N7 position of guanine. Like other bifunctional alkylating agents, it is active against both resting and rapidly dividing tumor cells. The levo-isomer - melphalan (L-sarcolysin) is approved under the brand name ALKERAN for the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. In addition, the drug was approved under the trade name Evomela. Evomela is indicated for use as a high-dose conditioning treatment prior to hematopoietic progenitor (stem) cell transplantation in patients with multiple myeloma. In addition, for the palliative treatment of patients with multiple myeloma for whom oral therapy is not appropriate.

Approval Year

PubMed

Title	Date	PubMed
[A clinical analysis of 25 cases of multiple myeloma complicated by extramedullary plasmacytomas].	2009-05	19615158
[Synthesis and properties of fluorescently-labelled triglyceride, derivative of the antineoplastic agent sarcolysin].	2004-03-26	15040307

Patents

Sample Use Guides

In Vivo Use Guide

Multiple Myeloma: The usual oral dose is 6 mg (3 tablets) daily. The entire daily dose may be given at one time. Epithelial Ovarian Cancer: at a dose of 0.2 mg/kg daily for 5 days as a single course. Courses are repeated every 4 to 5 weeks depending upon hematologic tolerance. For Conditioning Treatment: the recommended dose of Evomela is 100 mg/m2 /day administered over 30 minutes by intravenous infusion for 2 consecutive days (Day -3 and Day -2) prior to autologous stem cell transplantation (ASCT, Day 0). For Palliative Treatment: the recommended dose of Evomela is 16 mg/m2 administered as a single intravenous infusion over 15-20 minutes at 2-week intervals for 4 doses, then, after adequate recovery from toxicity, at 4-week intervals

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:51 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:51 GMT 2025`
Record UNII	A960M0G5TP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SARCOLYSIN

Official Name

English

MERPHALAN

Preferred Name

English

MELPHALAN DL-FORM [MI]

Common Name

English

ALANINE, 3-(P-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-, DL-

Common Name

English

MELPHALAN DL-FORM

Common Name

English

sarcolysin [INN]

Common Name

English

Sarcolysin [WHO-DD]

Common Name

English

DL-PHENYLALANINE, 4-(BIS(2-CHLOROETHYL)AMINO)-

Systematic Name

English

PHENYLALANINE, 4-(BIS(2-CHLOROETHYL)AMINO)-

Systematic Name

English

SARCOLYSIN, DL-

Common Name

English

MERPHALAN [IARC]

Common Name

English

DL-PHENYLALANINE MUSTARD

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697