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 The FDA withdrew its approval for the use of chlorhexidine gluconate topical tincture 0.5%, due to a significant number of reports concerning chemical and thermal burns associated with the use of this product.19,20 Other formulations of chlorhexidine continue to be available.
- Accession Number
- DBSALT000023
- Structure
Structure for Chlorhexidine gluconate (DBSALT000023)
- 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
- External Links
- KEGG Compound
- C08038
- PubChem Compound
- 9939931
- ChemSpider
- 4514538
- ChEBI
- 28312
- ChEMBL
- CHEMBL4297088
- Wikipedia
- Chlorhexidine
- Predicted Properties
Property Value Source Water Solubility 0.0261 mg/mL ALOGPS logP 2.71 ALOGPS logP 4.51 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) 10.52 Chemaxon Physiological Charge 4 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 10 Chemaxon Polar Surface Area 167.58 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 181.71 m3·mol-1 Chemaxon Polarizability 53.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon