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Chlormethine information


Chlormethine
Skeletal formula of chlormethine
Space-filling model of the chlormethine molecule
Names
IUPAC name
2-Chloro-N-(2-chloroethyl)-N-methylethanamine
Other names
  • Bis(2-chloroethyl)(methyl)amine
  • mechlorethamine
  • mustine
  • HN-2
  • Ledaga[1][2]
Identifiers
CAS Number
  • 51-75-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28925 checkY
ChEMBL
  • ChEMBL427 checkY
ChemSpider
  • 3893 checkY
DrugBank
  • DB00888 checkY
ECHA InfoCard 100.000.110 Edit this at Wikidata
EC Number
  • 200-120-5
KEGG
  • D0767 ☒N
MeSH Mechlorethamine
PubChem CID
  • 4033
RTECS number
  • IA1750000
UNII
  • 50D9XSG0VR checkY
UN number 2810
CompTox Dashboard (EPA)
  • DTXSID2020975 Edit this at Wikidata
InChI
  • InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 checkY
    Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N checkY
SMILES
  • CN(CCCl)CCCl
Properties
Chemical formula
C5H11Cl2N
Molar mass 156.05 g·mol−1
Appearance Colorless liquid
Odor Fishy, ammoniacal
log P 0.91
Pharmacology
ATC code
D08AX04 (WHO) L01AA05 (WHO)
Pregnancy
category
  • AU: B3[1]
Routes of
administration
  • Intracavitary
  • Intrapericardial
  • Intravenous
  • Topical
Pharmacokinetics:
Biological half-life
<1 minute
Excretion
50% (Kidney)
Legal status
  • AU: S4 (Prescription only)[1]
  • CA: ℞-only[3]
  • EU: Rx-only[2]
  • In general: ℞ (Prescription only)
Related compounds
Related amines
  • Dimethylamine
  • Trimethylamine
  • N-Nitrosodimethylamine
  • Diethylamine
  • Triethylamine
  • Diisopropylamine
  • Dimethylaminopropylamine
  • Diethylenetriamine
  • N,N-Diisopropylethylamine
  • Triisopropylamine
  • Tris(2-aminoethyl)amine
  • HN1 (nitrogen mustard)
  • HN3 (nitrogen mustard)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chlormethine (INN, BAN), also known as mechlorethamine (USAN, USP), mustine, HN2, and (in post-Soviet states) embikhin (эмбихин), is a nitrogen mustard sold under the brand name Mustargen among others. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drugs. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.[4][5][6]

  1. ^ a b c "Ledaga". Therapeutic Goods Administration (TGA). 30 June 2021. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
  2. ^ a b "Ledaga EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 5 September 2021. Retrieved 5 September 2021.
  3. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  4. ^ Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000). "Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro". Toxicol. Sci. 54 (1): 212–21. doi:10.1093/toxsci/54.1.212. PMID 10746948.
  5. ^ "Chapter 3: Principles of Oncologic Pharmacotherapy". Cancer Management: A Multidisciplinary Approach. 2010. Archived from the original on 15 May 2009. Retrieved 8 October 2023.
  6. ^ "CDC - The Emergency Response Safety and Health Database: Blister Agent: NITROGEN MUSTARD HN-2 - NIOSH". U.S. Centers for Disease Control and Prevention (CDC). Archived from the original on 2019-06-28. Retrieved 2016-04-20.

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