TRICHLORMETHINE

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Quantitation of biomarkers of exposure to nitrogen mustards in urine from rats dosed with nitrogen mustards and from an unexposed human population.	2004 Jul-Aug	15239850
An infinite water chain passes through an array of Zn(II) metallocycles built with a podand bearing terminal carboxylates.	2005 Feb 21	15859250
Trichloromethyl ketones as synthetically versatile donors: application in direct catalytic mannich-type reactions and the stereoselective synthesis of azetidines.	2006 May 5	16596693
Development of a liquid chromatography-multiple reaction monitoring procedure for concurrent verification of exposure to different forms of mustard agents.	2008 Jan-Feb	18269793
Sulfur mustard research--strategies for the development of improved medical therapy.	2008 Jun 10	18615149
Poly[[{μ(3)-tris-[2-(4-phenyl-1,2,3-triazol-1-yl)eth-yl]amine}silver(I)] hexa-fluorido-phosphate].	2008 Sep 13	21201012
Amplitude-modulated electromagnetic fields for the treatment of cancer: discovery of tumor-specific frequencies and assessment of a novel therapeutic approach.	2009 Apr 14	19366446
Development history and concept of an oral anticancer agent S-1 (TS-1): its clinical usefulness and future vistas.	2009 Jan	19052037
[Study on the influence factors of human peripheral blood B lymphocyte transformation by Epstein-Barr virus].	2009 Sep	19877506
Chemotherapy for early-stage breast cancer: a brief history.	2009 Sep	19756003
The role of funding and policies on innovation in cancer drug development.	2010	22276026
Biology-driven cancer drug development: back to the future.	2010 Apr 12	20385032
Ameliorative effect of DRDE 07 and its analogues on the systemic toxicity of sulphur mustard and nitrogen mustard in rabbit.	2010 Sep	20164158

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 Created by `admin` on `Fri Dec 15 15:57:21 GMT 2023` Edited by `admin` on `Fri Dec 15 15:57:21 GMT 2023`
Record UNII	66WBM7N0NM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRICHLORMETHINE

Official Name

English

NSC-260424

Code

English

TRIMUSTINE

Common Name

English

TRICHLORMETHINE [HSDB]

Common Name

English

TRICHLORMETHINE [MI]

Common Name

English

TRICHLORMETHINE [IARC]

Common Name

English

2,2',2''-TRICHLOROTRIETHYLAMINE

Common Name

English

trichlormethine [INN]

Common Name

English

Trichlormethine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697