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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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 11 Target ID: GO:0090592 Sources: https://monographs.iarc.fr/ENG/Monographs/vol50/mono50-11.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lymphoma 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2615874	Primary		Approved 8583	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153 Nav1.5 116	CYP2B6 776 CYP2C8 810 P-gp 2052 CYP2A6 626 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 2.0	inconclusive [IC50 0.1096 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 13.0	inconclusive [IC50 30.9008 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 88.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 135.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 126.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 127.0	no

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	likely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	major
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	minor
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results Page: 107 \| 109	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	weak
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	weak
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	weak
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12584152/	weak

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 119	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/22024336/
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5561#section=Biological-Test-Results \| https://pubmed.ncbi.nlm.nih.gov/16647228/ Page: 134.0

PubMed

Title	Date	PubMed
Ameliorative effect of DRDE 07 and its analogues on the systemic toxicity of sulphur mustard and nitrogen mustard in rabbit.	2010-09	20164158
Biology-driven cancer drug development: back to the future.	2010-04-12	20385032
The role of funding and policies on innovation in cancer drug development.	2010	22276026
[Study on the influence factors of human peripheral blood B lymphocyte transformation by Epstein-Barr virus].	2009-09	19877506
Chemotherapy for early-stage breast cancer: a brief history.	2009-09	19756003
Amplitude-modulated electromagnetic fields for the treatment of cancer: discovery of tumor-specific frequencies and assessment of a novel therapeutic approach.	2009-04-14	19366446
Development history and concept of an oral anticancer agent S-1 (TS-1): its clinical usefulness and future vistas.	2009-01	19052037
Poly[[{μ(3)-tris-[2-(4-phenyl-1,2,3-triazol-1-yl)eth-yl]amine}silver(I)] hexa-fluorido-phosphate].	2008-09-13	21201012
Sulfur mustard research--strategies for the development of improved medical therapy.	2008-06-10	18615149
Development of a liquid chromatography-multiple reaction monitoring procedure for concurrent verification of exposure to different forms of mustard agents.	2008-02-14	18269793
Trichloromethyl ketones as synthetically versatile donors: application in direct catalytic mannich-type reactions and the stereoselective synthesis of azetidines.	2006-05-05	16596693
An infinite water chain passes through an array of Zn(II) metallocycles built with a podand bearing terminal carboxylates.	2005-02-21	15859250
Quantitation of biomarkers of exposure to nitrogen mustards in urine from rats dosed with nitrogen mustards and from an unexposed human population.	2004-07-09	15239850

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 `Mon Mar 31 19:21:19 GMT 2025` Edited by `admin` on `Mon Mar 31 19:21:19 GMT 2025`
Record UNII	00238AP6R9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-30211

Preferred Name

English

TRICHLORMETHINE HYDROCHLORIDE

Common Name

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