Dequalinium

Dequalinium is a quaternary ammonium cation and bolaamphiphile commonly available as the dichloride salt. The bromide, iodide, acetate, and undecenoate salts are known as well. Dequalinium chloride is the active ingredient of several medications:

Dequalinium chloride
Names
IUPAC name
1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium) decyl]-2-methyl-4-quinolin-1-iumamine dichloride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.575
MeSH Dequalinium
PubChem CID
UNII
InChI
  • InChI=1S/C30H38N4/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3/p+2 Y
    Key: PCSWXVJAIHCTMO-UHFFFAOYSA-P Y
  • InChI=1/C30H38N4/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3/p+2
    Key: PCSWXVJAIHCTMO-SKRXCDHZAO
SMILES
  • c12ccccc1c(cc([n+]2CCCCCCCCCC[n+]4c3ccccc3c(N)cc4C)C)N
Properties
Chemical formula
 C30H40N4
Molar mass 456.678 g·mol−1
Pharmacology
D08AH01 (WHO) G01AC05 (WHO), R02AA02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Dequadin an antiseptic and disinfectant. It is a topical bacteriostat. It is used in wound dressings and mouth infections and may also have antifungal action. It may cause skin ulceration.

Fluomizin, vaginal tablets containing 10 mg dequalinium chloride, are used for treating vaginal bacterial conditions (i.e. Bacterial Vaginosis and aerobic vaginitis).

The dequalinium dication is symmetrical, containing two quaternary quinolinium units linked by an N-decylene chain.

Applications

Dequalinium salts may be used to treat malaria.[1][2] As dequalinium chloride, it can be used in lozenges to cure tonsillitis, but this is not effective in cases of streptococci infections.[3]

References
  1. Tischer, Maximilian; Pradel, Gabriele; Ohlsen, Knut; Holzgrabe, Ulrike (2012-01-02). "Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions?". ChemMedChem. 7 (1): 22–31. doi:10.1002/cmdc.201100404. ISSN 1860-7187. PMID 22113995. S2CID 26326417.
  2. "US Patent 4946849". United States Patents and Trademarks Office (USPTO). 10 October 1989. Retrieved 2008-03-15.
  3. Krämer W. (1977). "[Treatment of tonsilitis with dequalinium chloride]". Fortschr. Med. (in German). 95 (16): 1108–10. PMID 856702.

Further reading
  • Gamboa-Vujicic, Gisela; Emma, Dennis A.; Liao, Shu Y.; Fuchtner, Carlos; Manetta, Alberto (1993). "Toxicity of the mitochondrial poison dequalinium chloride in a murine model system". Journal of Pharmaceutical Sciences. 82 (3): 231–5. doi:10.1002/jps.2600820302. PMID 8450414.


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