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