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.
In the Vinony graph
Within Vinony's link graph, chlornaphazine is referenced by 4 other articles, and connects out to adaptive radiation therapy, cytostasis and red blood cell.
It is catalogued under topics including 2-Naphthyl compounds, Alkylating antineoplastic agents and Chembox image size set.
Its subject is documented across 8 Wikipedia language editions.
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Withdrawn- Max clinical phase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.