TRICHLORMETHINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H12Cl3N.ClH
Molecular Weight	240.986
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TRICHLORMETHINE HYDROCHLORIDE

Structure Search

SMILES

Cl.ClCCN(CCCl)CCCl

InChI

InChIKey=VEAUDLLZYJVHRI-UHFFFAOYSA-N

InChI=1S/C6H12Cl3N.ClH/c7-1-4-10(5-2-8)6-3-9;/h1-6H2;1H

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Description
Sources: http://www.inchem.org/documents/iarc/vol50/06-trichlormethine.html
Curator's Comment: The description was created based on several sources, including https://monographs.iarc.fr/ENG/Monographs/vol50/mono50-11.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2615874 | https://www.ncbi.nlm.nih.gov/pubmed/6188044

Trichlormethine is a nitrogen mustard vesicant that has application in chemical warfare and has been used as a cytostatic alkylating agent in leukemia and lymphoma therapy. Trichlormethine was tested for carcinogenicity by subcutaneous injection in mice and rats. The study in mice was inadequate for evaluation. In rats, trichlormethine induced a high incidence of sarcomas (mostly spindle-cell type) in animals of each sex at the site of subcutaneous injection, as well as a few intestinal adenocarcinomas; neither tumor type was seen in controls. Trichlormethine caused vomiting, anorexia and blood-containing feces in dogs a few hours after a single intravenous injection of 1 mg/kg BW. Decreased peripheral lymphocyte counts were observed in rabbits injected intravenously and in mice injected subcutaneously with trichlormethine. Trichlormethine was tested for carcinogenicity by subcutaneous injection in mice and rats. ln rats, trichlormethine induced a high incidence of sarcomas (mostly spindle-cell type) in animals of each sex at the site of subcutaneous injection, as well as a few intestinal adenocarcinomas; neither tumor type was seen in controls. Trichlormethine is possibly carcinogenic to humans (Group 2B).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA synthesis involved in DNA replication 7 Target ID: GO:0090592 Sources: https://monographs.iarc.fr/ENG/Monographs/vol50/mono50-11.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lymphoma 58 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2615874	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

A group of 20 mice (age, strain and sex unspeified) received weekly subcutaneous injections of trichlormethine (purity unspeified) at 1mg/kg bw in aqueous solution for ten weeks, afer which time only four mice were alive and treatment was terminated.

Route of Administration: Other

In Vitro Use Guide

About 2 x 10^6 exponentially growing V79 cells (3.5 x l0^4 cells/cm 2) were treated with 0-10 mkg TS160/ml. (TSl60 was diluted in complete medium, in a medium without serum or in PBS buffer.) Then the cells were washed, resuspended by means of 0.025% trypsin in 0.02% EDTA and tested for their growth activity, plating efficiency, the course of macromolecular syntheses and for the presence of 6-thioguanine-resistant (6-TGr) mutants. The treated cells were plated on a series of Petri dishes, diameter 5 cm (4 x 10^4 cells per dish) and incubated at 37°C. At 24-h intervals, the cells were removed from individual Petri dishes and the numbers of cells/dish were counted. The cytostatic agent TSt60 inhibited DNA synthesis in V79 cells while the course of RNA synthesis and protein synthesis were not changed significantly.

Name

Type

Language

TRICHLORMETHINE HYDROCHLORIDE

Common Name

English

NSC-30211

Code

English

TRICHLORMETHINE HCL

Common Name

English

TRICHLORMETHINE HYDROCHLORIDE [MI]

Common Name

English

NSC-759837

Code

English

TRIMUSTINE HYDROCHLORIDE

Common Name

English

Trichlormethine hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

MERCK INDEX

m11060