Structure via PubChem · Public domain (PubChem)
chlornaphazine
Sign in to saveAlso known as N,N-Bis(2-chloroethyl)-2-naphthylamine
Chlornaphazine, a derivative of 2-naphthylamine, is a nitrogen mustard that was developed in the 1950s for the treatment of polycythemia and Hodgkin's disease. However, a high incidence of bladder cancers in patients receiving treatment with chlornaphthazine led to use of the drug being discontinued.
Chemical data
- Formula
- C14H15Cl2N
- Molecular weight
- 268.2 g/mol
- IUPAC name
- N,N-bis(2-chloroethyl)naphthalen-2-amine
- SMILES
- C1=CC=C2C=C(C=CC2=C1)N(CCCl)CCCl
- InChIKey
- XCDXSSFOJZZGQC-UHFFFAOYSA-N
- XLogP
- 4.5
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 267.058
Show 4 more facts
- chemical formula
- C₁₄H₁₅Cl₂N
- canonical SMILES
- C1=CC=C2C=C(C=CC2=C1)N(CCCl)CCCl
- Commons category
- Chlornaphazine
- subject has role
- carcinogen
via Wikidata · CC0
~11 min read
Encyclopedic overview
11 sectionsContents
- History
- Medical use
- Discontinued use
- Mechanism of action
- Reactivity
- Metabolism
- Efficacy
- Adverse effects
- Toxicity
- Effects on animals
- References
Chlornaphazine, a derivative of 2-naphthylamine, is a nitrogen mustard that was developed in the 1950s for the treatment of polycythemia and Hodgkin's disease. However, a high incidence of bladder cancers in patients receiving treatment with chlornaphthazine led to use of the drug being discontinued.
The International Agency for Research on Cancer has listed chlornaphazine as a human carcinogen.
Excerpted from Wikipedia’s “chlornaphazine” article, available under the CC BY-SA 4.0 licence.