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Details

Stereochemistry ACHIRAL
Molecular Formula C6H12Cl3N
Molecular Weight 204.525
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICHLORMETHINE

SMILES

ClCCN(CCCl)CCCl

InChI

InChIKey=FDAYLTPAFBGXAB-UHFFFAOYSA-N
InChI=1S/C6H12Cl3N/c7-1-4-10(5-2-8)6-3-9/h1-6H2

HIDE SMILES / InChI

Molecular Formula C6H12Cl3N
Molecular Weight 204.525
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

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.
Substance Class Chemical
Record UNII
66WBM7N0NM
Record Status Validated (UNII)
Record Version