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Details

Stereochemistry ACHIRAL
Molecular Formula C5H11Cl2NO.ClH
Molecular Weight 208.514
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECHLORETHAMINE OXIDE HYDROCHLORIDE

SMILES

Cl.C[N+]([O-])(CCCl)CCCl

InChI

InChIKey=SYNHCENRCUAUNM-UHFFFAOYSA-N
InChI=1S/C5H11Cl2NO.ClH/c1-8(9,4-2-6)5-3-7;/h2-5H2,1H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00888 and http://chemocare.com/chemotherapy/drug-info/Mechlorethamine.aspx

Mechlorethamine Oxide was approved by the FDA in 1949 for the treatment of hematologic malignancies, alkylating agents are the oldest class of anticancer agents. A biologic alkylating agent exerts its cytotoxic effects by forming DNA adducts and DNA interstrand crosslinks, thereby inhibiting rapidly proliferating cells. Mechlorethamine Oxide is an antineoplastic agent used to treat Hodgkin desease and Lymphoma. Known under the brand names of Mustargen and Valchlor in USA. The FDA granted marketing approval for the orphan drug Valchlor (mechlorethamine) gel on August 23, 2013 for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma (CTCL) in patients who have received prior skin-directed therapy. Each tube of Valchlor contains 0.016% of mechlorethamine which is equivalent to 0.02% mechlorethamine HCL.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Mustargen

Approved Use

Mustargen, administered intravenously, is indicated for the palliative treatment of Hodgkin’s disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Mustargen, administered intrapleurally, intraperitoneally, or intrapericardially, is indicated for the palliative treatment of metastatic carcinoma resulting in effusion.

Launch Date

1949
Palliative
Mustargen

Approved Use

Mustargen, administered intravenously, is indicated for the palliative treatment of Hodgkin’s disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Mustargen, administered intrapleurally, intraperitoneally, or intrapericardially, is indicated for the palliative treatment of metastatic carcinoma resulting in effusion.

Launch Date

1949
Palliative
Mustargen

Approved Use

Mustargen, administered intravenously, is indicated for the palliative treatment of Hodgkin’s disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Mustargen, administered intrapleurally, intraperitoneally, or intrapericardially, is indicated for the palliative treatment of metastatic carcinoma resulting in effusion.

Launch Date

1949
PubMed

PubMed

TitleDatePubMed
In vitro neurotoxic and DNA-damaging properties of nitrogen mustard.
2000 Dec
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
2014 Jun 12
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Mustargen, administered intrapleurally, intraperitoneally, or intrapericardially, is indicated for the palliative treatment of metastatic carcinoma resulting in effusion.
A total dose of 0.4 mg/kg of body weight for each course usually is given either as a single dose or in divided doses of 0.1 to 0.2 mg/kg per day.
Route of Administration: Intravenous
Extensive cell loss (>90%) was observed in rat neuronal and SY5Y neuroblastoma cell cultures treated with 10 uM Mechlorethamine oxide
Name Type Language
MECHLORETHAMINE OXIDE HYDROCHLORIDE
MI  
Common Name English
CHLORMETHINE OXIDE HYDROCHLORIDE
WHO-DD  
Common Name English
NITROGEN MUSTARD N-OXIDE HYDROCHLORIDE [JAN]
Common Name English
METHYLBIS(.BETA.-CHLOROETHYL)AMINE N-OXIDE HYDROCHLORIDE
Systematic Name English
2-CHLORO-N-(2-CHLOROETHYL)-N-METHYLETHANAMINE-N-OXIDE HYDROCHLORIDE
Systematic Name English
NITROMIN
Brand Name English
NITROGEN MUSTARD N-OXIDE HYDROCHLORIDE [HSDB]
Common Name English
N-METHYLBIS(2-CHLOROETHYL)AMINE N-OXIDE HYDROCHLORIDE
Systematic Name English
MITOMEN
Brand Name English
N-METHYL-2,2'-DICHLORODIETHYLAMINE N-OXIDE HYDROCHLORIDE
Common Name English
ETHANAMINE, 2-CHLORO-N-(2-CHLOROETHYL)-N-METHYL-, N-OXIDE, HYDROCHLORIDE
Systematic Name English
2,2'-DICHLORO-N-METHYLDIETHYLAMINE N-OXIDE HYDROCHLORIDE
Common Name English
MUSTRON
Brand Name English
NITROGEN MUSTARD N-OXIDE HYDROCHLORIDE
HSDB   JAN  
Common Name English
METHYLDI(2-CHLOROETHYL)AMINE N-OXIDE HYDROCHLORIDE
Systematic Name English
NITROMIN HYDROCHLORIDE
Common Name English
METHYLBIS(.BETA.-CHLOROETHYL)AMINE OXIDE HYDROCHLORIDE
Systematic Name English
MECHLORETHAMINE OXIDE HYDROCHLORIDE [MI]
Common Name English
MECHLORETHAMINE OXIDE HCL
Common Name English
DIETHYLAMINE, 2,2'-DICHLORO-N-METHYL-, N-OXIDE, COMPD. WITH HYDROCHLORIC ACID
Common Name English
Chlormethine oxide hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C628
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
CAS
302-70-5
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
EVMPD
SUB01221MIG
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
PUBCHEM
9334
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
SMS_ID
100000084712
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL427
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
HSDB
5106
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
FDA UNII
009L92D6OC
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY
MERCK INDEX
m7117
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID0023375
Created by admin on Fri Dec 15 18:32:21 GMT 2023 , Edited by admin on Fri Dec 15 18:32:21 GMT 2023
PRIMARY