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Details

Stereochemistry ACHIRAL
Molecular Formula C5H11Cl2NO
Molecular Weight 172.053
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECHLORETHAMINE OXIDE

SMILES

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

InChI

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

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
MI  
Common Name English
2,2'-DICHLORO-N-METHYLDIETHYLAMINE-N-OXIDE
Systematic Name English
MECHLORETHAMINE OXIDE [MI]
Common Name English
NMO
Common Name English
NITROGEN MUSTARD N-OXIDE [IARC]
Common Name English
NSC-141949
Code English
NITROGEN MUSTARD N-OXIDE
Common Name English
ETHANAMINE, 2-CHLORO-N-(2-CHLOROETHYL)-N-METHYL-, N-OXIDE
Systematic Name English
METHYLBIS(.BETA.-CHLOROETHYL)AMINE N-OXIDE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID7020976
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY
NSC
141949
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY
PUBCHEM
9335
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY
FDA UNII
2Q86QAR1PN
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY
CAS
126-85-2
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY
MERCK INDEX
m7117
Created by admin on Fri Dec 15 18:20:31 GMT 2023 , Edited by admin on Fri Dec 15 18:20:31 GMT 2023
PRIMARY Merck Index