U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C30H40N4.2C11H19O2
Molecular Weight 823.2001
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEQUALINIUM UNDECENATE

SMILES

[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C.CC1=[N+](CCCCCCCCCC[N+]2=C(C)C=C(N)C3=C2C=CC=C3)C4=C(C=CC=C4)C(N)=C1

InChI

InChIKey=ADVZBZHXUINOFY-UHFFFAOYSA-N
InChI=1S/C30H38N4.2C11H20O2/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;2*1-2-3-4-5-6-7-8-9-10-11(12)13/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*2H,1,3-10H2,(H,12,13)

HIDE SMILES / InChI

Molecular Formula C11H20O2
Molecular Weight 184.2753
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C30H38N4
Molecular Weight 454.6495
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dequalinium is a quaternary ammonium cation commonly available as the dichloride salt. Dequalinium chloride has an antiseptic effect against a wide range of bacteria, yeasts, and some fungi and viruses. It kills the micro-organisms associated with various mild infections of the mouth and throat. Also, Dequalinium chloride is active against the bacteria which cause bacterial vaginosis. Dequalinium Chloride (DECA) is a PKC inhibitor and high-affinity blocker CNGA1 channel, and nearly as effective on heteromeric CNGA1+CNGB1 channels. Common side effects are: vaginal discharge; vaginal itching or vaginal burning; vaginal yeast infection (thrush); tender tongue.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.5 µM [Ki]
14.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Fluomizin
Curative
Dequadin lozenges
Curative
Dequadin lozenges
Curative
Dequadin lozenges

PubMed

Sample Use Guides

In Vivo Use Guide
1 vaginal tablet (10 mg) daily for 6 days
Route of Administration: Other
In Vitro Use Guide
multidrug-resistant lines were less sensitive than parental cell lines to the intrinsic growth inhibitory effects of dequalinium (IC50, 4.4 versus 0.3 microM in multidrug-resistant and sensitive P388 cells, respectively).
Substance Class Chemical
Record UNII
89J4L3V7VP
Record Status Validated (UNII)
Record Version