METAMELFALAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H18Cl2N2O2
Molecular Weight	305.2
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CC1=CC(=CC=C1)N(CCCl)CCCl)C(O)=O

InChI

InChIKey=QDGAVODICPCDMU-LBPRGKRZSA-N

InChI=1S/C13H18Cl2N2O2/c14-4-6-17(7-5-15)11-3-1-2-10(8-11)9-12(16)13(18)19/h1-3,8,12H,4-7,9,16H2,(H,18,19)/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H18Cl2N2O2
Molecular Weight	305.2
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://pubs.rsc.org/en/content/articlelanding/1954/jr/jr9540002409#!divAbstract | https://www.ncbi.nlm.nih.gov/pubmed/14174040 | https://medkoo.com/products/20742 | https://link.springer.com/book/10.1007/978-1-4757-2085-3#about

Metamelfalan is an antineoplastic agent. Metamelfalan is the meta form of the levo isomer melphalan. Metamelfalan causes crosslinking of DNA, thereby preventing DNA replication and eventually cellular proliferation.

Approval Year

PubMed

Title	Date	PubMed
POTENTIAL ANTICANCER AGENTS. LXXX. ALKYLATING AGENTS RELATED TO PHENYLALANINE MUSTARD. VI. ENANTIOMERIC META-PHENYLALANINE MUSTARDS.	1963-01	14174040

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:29:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:29:30 GMT 2025`
Record UNII	3B30XBE7S2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METAMELFALAN

Official Name

English

NSC-67781

Preferred Name

English

ALANINE, 3-(M-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-, L-

Systematic Name

English

L-M-SARCOLYSIN

Common Name

English

3-(M-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-L-ALANINE

Systematic Name

English

Metamelfalan [WHO-DD]

Common Name

English

L-PHENYLALANINE, 3-(BIS(2-CHLOROETHYL)AMINO)-

Systematic Name

English

3-(BIS(2-CHLOROETHYL)AMINO)-L-PHENYLALANINE

Systematic Name

English

metamelfalan [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697