U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of SARCOLYSIN

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
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

PubMed

TitleDatePubMed
[Synthesis and properties of fluorescently-labelled triglyceride, derivative of the antineoplastic agent sarcolysin].
2004 Jan-Feb
[A clinical analysis of 25 cases of multiple myeloma complicated by extramedullary plasmacytomas].
2009 May
Patents

Patents

Sample Use Guides

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
Name Type Language
SARCOLYSIN
INN  
INN  
Official Name English
MELPHALAN DL-FORM [MI]
Common Name English
ALANINE, 3-(P-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-, DL-
Common Name English
MELPHALAN DL-FORM
MI  
Common Name English
sarcolysin [INN]
Common Name English
Sarcolysin [WHO-DD]
Common Name English
MERPHALAN
WHO-DD  
Brand 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
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL429405
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
PUBCHEM
4053
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID9031569
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
NCI_THESAURUS
C61936
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
INN
2143
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
FDA UNII
A960M0G5TP
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
MERCK INDEX
m7166
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY Merck Index
EVMPD
SUB10448MIG
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
SMS_ID
100000084075
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY
CAS
531-76-0
Created by admin on Fri Dec 15 16:05:49 GMT 2023 , Edited by admin on Fri Dec 15 16:05:49 GMT 2023
PRIMARY