Chlorhexidine gluconateProduct ingredient for Chlorhexidine

Name
Chlorhexidine gluconate
Drug Entry
Chlorhexidine

Chlorhexidine is a broad-spectrum antimicrobial biguanide used as a topical antiseptic and in dental practice for the treatment of inflammatory dental conditions caused by microorganisms.11 It is one of the most common skin and mucous membrane antiseptic agents in use today.2 The molecule itself is a cationic bis-guanide consisting of two 4-chlorophenyl rings and two biguanide groups joined by a central hexamethylene chain.7 Topical chlorhexidine for disinfection, as well as oral rinses for dental use, carries activity against a broad range of pathogens including bacteria, yeasts, and viruses.12,11,7

Chlorhexidine was developed in the UK by Imperial Chemical Industries in the early 1950s9 and was introduced to the US in the 1970s.18

Accession Number
DBSALT000023
Structure
Thumb
Synonyms
Not Available
UNII
MOR84MUD8E
CAS Number
18472-51-0
Weight
Average: 897.76
Monoisotopic: 896.3198019
Chemical Formula
C34H54Cl2N10O14
InChI Key
YZIYKJHYYHPJIB-UUPCJSQJSA-N
InChI
InChI=1S/C22H30Cl2N10.2C6H12O7/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18;2*7-1-2(8)3(9)4(10)5(11)6(12)13/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*2-5,7-11H,1H2,(H,12,13)/t;2*2-,3-,4+,5-/m.11/s1
IUPAC Name
bis((2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid); N-(4-chlorophenyl)-1-{N'-[6-(N-{[N'-(4-chlorophenyl)carbamimidamido]methanimidoyl}amino)hexyl]carbamimidamido}methanimidamide
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1
KEGG Compound
C08038
PubChem Compound
9939931
ChemSpider
4514538
ChEBI
28312
ChEMBL
CHEMBL4297088
Wikipedia
Chlorhexidine
Predicted Properties
PropertyValueSource
Water Solubility0.0261 mg/mLALOGPS
logP2.71ALOGPS
logP4.51ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area167.58 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity181.71 m3·mol-1ChemAxon
Polarizability53.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon