Chlorhexidine

Synonyms :
1,1′-Hexamethylene bis(5-(P-chlorophenyl)biguanide), Chlorhexidin, Chlorhexidine, Chlorhexidinum, Cloresidina, Clorhexidina, N,N’-bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide

Status : approved

Category

Anti-Infective Agents

Therapeutic Classification

STOMATOLOGICAL PREPARATIONS

ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Anti-Infective Agents, Local

Description

A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque. [PubChem]

Used

For reduction of pocket depth in patients with adult periodontitis, used as an adjunct to scaling and root planing procedures. Also for prevention of dental caries, oropharyngeal decontamination in critically ill patients, hand hygiene in health-care personnel, general skin cleanser, and catheter site preparation and care.

Mechanism Of Action

Chlorhexidine’s antimicrobial effects are associated with the attractions between chlorhexidine (cation) and negatively charged bacterial cells. After chlorhexidine is absorpted onto the organism’s cell wall, it disrupts the integrity of the cell membrane and causes the leakage of intracellular components of the organisms.

Dosage

Form Route Strength
Lotion topical 8.3; 506.3 mg/mL; mg/mL
Sponge topical (hospital/hc facilities) 2 %
Liquid oral .12 mg/mL
Wipe topical 2 %
Solution topical 2 %
Solution topical 4 g/100mL
Solution topical 2 g/100g
Solution topical 2 g/100mL
Liquid oral 0.12 %
Dressing topical .5 %
Sponge topical 40 mg/mL
Solution topical 20 mg/mL
Solution topical 40 mg/mL
Liquid topical 0.05 %
Liquid topical 20 %
Solution topical .5 %
Solution topical 40 g/1000mL
Solution topical .04 mg/mL
Spray topical .5 %
Solution topical 20; .7 mg/mL; mL/mL
Liquid topical .5 %
Pad topical 0.5 %
Swab topical 0.5 %
Cloth topical 500 mg
Rinse oral .12 mg/mL
Rinse oral 1.2 mg/mL
Liquid buccal 1.2 [iU]/mL
Liquid; mouthwash/gargle oral 0.12 %
Solution topical 0.05 %
Solution topical 20 %
Liquid topical .05 %
Liquid topical 0.5 mg
Liquid; mouthwash/gargle buccal; oral 0.12 %
Liquid dental .12 g/mL
Lotion topical 4 %
Liquid topical 0.5 %
Liquid topical 2 %
Liquid topical 4 %
Liquid topical 2 g/100mL
Sponge topical 4 %
Liquid topical 4.0 %
Cream topical 2 mg
Liquid topical 2 %
Liquid topical 4 %
Liquid topical 4 g/100mL
Gel topical 2 %
Gel topical 4 %
Gel topical 0.5 %
Mouthwash/gargle buccal 0.12 %
Solution topical (household) 4 %
Solution topical 213 g/1000mL
Solution topical .525; 70 g/5mL; g/5mL
Solution topical 4 %
Gel topical .5 %
Gel topical 2 %
Cream topical 2 %
Swab topical 2.0 %
Pad topical (household) 2 %
Solution topical (household) 2 %
Wipe topical (household) 2 %
Liquid buccal 0.12 %
Ointment topical 1 %
Liquid; mouthwash/gargle buccal 0.12 %
Insert, extended release periodontal 2.5 mg
Liquid buccal; oral 0.12 %
Liquid oral 1.2 mg/mL
Solution buccal 0.12 %
Liquid topical .12 %
Solution topical 1 mg/25mL
Solution topical 31.5; .7 mg/mL; mL/mL
Solution; kit dental 10 %
Lotion topical 2 %
Solution topical .7; .01 g/mL; g/mL
Solution topical .75 mg/100mL
Solution topical 4 mg/100mL
Liquid topical 4 mg/100mL
Soap bar topical 4 %
Lotion topical 2.0 %
Lotion topical 2.25 %
Liquid; sponge topical 4 %
Solution topical (hospital/hc facilities) 2.0 %
Sponge topical (hospital/hc facilities) 4 %
Aerosol topical 4 %
Solution topical (hospital/hc facilities) 2 %
Sponge topical (hospital/hc facilities) 2 %
Swab topical (hospital/hc facilities) 2 %
Wipe topical (hospital/hc facilities) 2 %
Sponge topical (hospital/hc facilities) 0.05 %
Solution; sponge topical (hospital/hc facilities) 0.5 %
Swab topical (hospital/hc facilities) 0.5 %
Wipe topical (hospital/hc facilities) 0.5 %
Swab topical (hospital/hc facilities) 2 %
Wipe topical (hospital/hc facilities) 2 %
Aerosol topical 0.5 %
Spray topical 0.5 %
Solution topical 2 %
Solution topical 4 %
Liquid topical .5 %
Spray topical (household) 2 %
Liquid dental .12 g/100mL

Pharmacodynamics

Chlorhexidine, a topical antimicrobial agent, is bactericidal. Because of its positive charge, the chlorhexidine molecule reacts with the microbial cell surface to destroy the integrity of the cell membrane. This novel mechanism of action makes it highly unlikely for the development of bacterial resistance.

Toxic Effect

LD50= 2g/kg (human, oral); LD50= 3 g/kg (rat, oral); LD50= 2.5 g/kg (mice, oral); LD50= 21 mg/kg (male rat, IV); LD50= 23 mg/kg (female rat, IV); LD50= 25 mg/kg (male mice, IV); LD50= 24 mg/kg (female mice, IV); LD50= 1g/kg (rat, subcutaneous); LD50= 637 mg/kg (male mice, subcutaneous); LD50= 632 mg/kg (female mice, subcutaneous)

Absorption

Absorption of chlorhexidine from the gastrointestinal tract is very poor. Additionally, an in vivo study in 18 adult patients found no detectable plasma or urine chlorhexidine concentrations following insertion of four periodontal implants under clinical conditions.

Protein Binding

87%

Elimination Route

Excretion of chlorhexidine gluconate occurred primarily through the feces (~90%). Less than 1% of the chlorhexidine gluconate ingested by these subjects was excreted in the urine.

Chemical Classification

This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.

Chlorobenzenes

Organic compounds

Benzenoids

Benzene and substituted derivatives

Halobenzenes

Salt : Chlorhexidine acetate

Chemical Name

1,1′-Hexamethylene bis(5-(P-chlorophenyl)biguanide)

Brands

name Dosage form Country
3m Avagard lotion US
3m Soluprep Sponge sponge Canada
Acclean Chlorhexidine Gluconate 0.12% Oral Rinse liquid US
Acclean Chlorhexidine Gluconate 0.12% Oral Rinse liquid US
Antiseptic Body Cleanser wipe Canada
Antiseptic Cleanser Solution solution Canada
Antiseptic First Aid Spray liquid Canada
Antiseptic Lotion Soap 2% lotion Canada
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser solution US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid Canada
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Antiseptic Skin Cleanser liquid US
Aplicare Antiseptic Chlorhexidine Gluconate solution US
Aplicare Antiseptic Chlorhexidine Gluconate solution US
Aplicare Antiseptic Chlorhexidine Gluconate solution US
Aplicare Antiseptic Chlorhexidine Gluconate solution US
Aplicare Chlorhexidine Gluconate 2% Solution solution US
Apo-chlorhexidine Oral Rinse liquid Canada
Avidene Surgical Scrub liquid Canada
Bacti-stat Chg liquid Canada
Bactigras dressing Canada
Bactoshield sponge US
Bactoshield Chg solution US
Bactoshield Chg solution US
Bactoshield Chg 2% liquid Canada
Bactoshield Chg 4% liquid Canada
Baxedin 2% – 70% solution Canada
Baxedin Liq 0.05% liquid Canada
Baxedin Liq 20% liquid Canada
Baxedin Pre-op solution Canada
Bd E-z Scrub solution US
Bd E-z Scrub solution US
Bd E-z Scrub 107 solution US
Betasept solution US
Burn O Sol Spray spray Canada
Calgon Vestal 2% Chg Antimicrob.skin Cleans. liquid Canada
Calgon Vestal 4% Chg Antimicrob.skin Cleans. liquid Canada
Cardinal Health liquid US
Chloraprep Liq 0.5% liquid Canada
Chloraprep One-step solution Canada
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chloraprep One-step solution US
Chlorhexidine 0.5% Liq liquid Canada
Chlorhexidine 2% Antiseptic Hand Wash solution Canada
Chlorhexidine 4% Antiseptic Hand Wash solution Canada
Chlorhexidine and Isopropyl Alcohol Prep Pads pad Canada
Chlorhexidine and Isopropyl Alcohol Swabsticks swab Canada
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate cloth US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate rinse US
Chlorhexidine Gluconate 0.12% Oral Rinse liquid US
Chlorhexidine Gluconate 0.12% Oral Rinse, USP liquid; mouthwash/gargle Canada
Chlorhexidine Gluconate 0.12% Oral Rinse, USP liquid; mouthwash/gargle Canada
Chlorhexidine Gluconate Solution 0.05% solution Canada
Chlorhexidine Gluconate Solution USP 20% solution Canada
Chlorhexidine Liq 0.05% liquid Canada
Chlorhexidine Solution solution Canada
Chlorhexseptic-liq 0.5mg/ml liquid Canada
Cida-stat Foam liquid Canada
Cida-stat Liq liquid Canada
Denti-care Chlorhexidine Gluconate Oral Rinse 0.12% liquid; mouthwash/gargle Canada
Denti-care Denti-rinse Chlorhexidine Gluconate Oral Rinse liquid US
Dermsafe Chlorhexidine Gluconate Hand Sanitizer Lotion lotion Canada
Dermsafe Pc lotion Canada
Dexidin 0.5 Solution liquid Canada
Dexidin 2 Detergent liquid Canada
Dexidin 2 Solution liquid Canada
Dexidin 20 Sol 20mg liquid Canada
Dexidin Liq 4% liquid Canada
Dyna-hex 2 liquid US
Dyna-hex 4 solution US
Dyna-hex 75 solution US
E-z Scrub 107 sponge Canada
E-z Scrub 747 4% liquid Canada
E-z Scrub Antimicrobial Foam Solution Containing 4% Chg liquid Canada
Endure 400 Scrub-stat 4 liquid Canada
Endure 420 Cida-stat liquid Canada
First Aid Antiseptic Skin Cleanser liquid Canada
Flamazine C cream Canada
Foam Care Chg Surgical Hand Scrub liquid Canada
Foam Care Chg Surgical Hand Scrub liquid Canada
Foam Safe liquid US
Germi Stat Gel 2% gel Canada
Germi Stat Gel 4% gel Canada
Germi-stat 0.5% Antiseptic Prep Gel gel Canada
Germi-stat 2% Foaming Liquid liquid Canada
Germi-stat Prep Gel liquid Canada
Gum Paroex mouthwash/gargle Canada
Henry Schein Antimicrobial Skin Cleanser gel Canada
Hexirex Antiseptic Skin Cleanser solution Canada
Hibiclens solution US
Hibiclens solution US
Hibiclens solution US
Hibiclens solution US
Hibiclens Antiseptic/antimicrobial Skin Cleanser liquid Canada
Hibidil solution Canada
Hibistat solution US
Hibistat Germicidal Hand Rinse liquid Canada
Hibitane Skin Cleanser solution Canada
Hibitane Skin Cleanser 2% liquid Canada
Hibitane Skin Cleanser 4% liquid Canada
Hibitane Skin Cleanser Liq 4% liquid Canada
Hygenipak 2% Chg Skin Cleanser liquid Canada
Hygienipak 2% Chg Foaming Skin Cleanser liquid Canada
Hygienipak 4% Chg Foaming Skin Cleanser liquid Canada
Hygienipak 4% Chg Skin Cleanser liquid Canada
Ic-gel gel Canada
Instillagel gel Canada
Laura Line Antibacterial Cream Soap 2% cream Canada
Laura Line Chlorhexidine Antiseptic Soap liquid Canada
Loris – I.V. swab Canada
Loris 2% Chg Body Cleanser/nettoyant Pour Le Corps pad Canada
Loris 2% Chg Solution solution Canada
Loris 2% Chg Wipe/serviette wipe Canada
Oro-clear liquid Canada
Oro-clense Oral Rinse – Liq 0.12% liquid Canada
Oronine H Ointment 1% ointment Canada
Ostar Antimicrobial Hand Soap 2% – Liquid liquid Canada
Paroex rinse US
Perichlor liquid Canada
Peridex rinse US
Peridex Oral Rinse liquid; mouthwash/gargle Canada
Peridex Oral Rinse 0.12% liquid; mouthwash/gargle Canada
Periochip insert, extended release US
Periochip insert, extended release US
Periogard liquid Canada
Periogard liquid US
Periogard Alcohol Free solution Canada
Perioselect Antimicrobial Sol 0.12% liquid Canada
Pre-scrub Ii Surgical Hand Scrub solution US
Prevantics Maxi Swabstick solution US
Prevantics Maxi Swabstick solution US
Prevantics Swab solution US
Prevantics Swab solution US
Prevantics Swabstick solution US
Prevantics Swabstick solution US
Prevantics Swabstick solution US
Prevora Stage 1 solution; kit Canada
Pro-dentx Chlorhexidene Oral Rinse liquid Canada
Provon Antiseptic Lotion Soap With 2% Chg lotion Canada
Purmist solution US
Purmist solution US
Purmist solution US
Purmist solution US
Rougier Clean Derm solution Canada
Rougier Vap-chlorhexidine Gluconate 2% W/V solution Canada
Rouhex G 20% liquid Canada
Rouhex G 4% liquid Canada
Rouhex G Liq 2% liquid Canada
Scrub solution US
Scrub Care solution US
Scrub Care Exidine -4 CHG liquid US
Scrub Care Exidine -4 CHG liquid US
Scrub Care Exidine -4 CHG liquid US
Scrub Care Surgical Scrub Brush/nail Cleaner With Exidine 4 solution Canada
Scrub Stat 4 Foam Liq liquid Canada
Scrub-stat solution US
Scrub-stat solution US
Scrub-stat IV 4% soap bar Canada
Seaqua X lotion Canada
Skinvisible Chlorhexidine Formula Hand Sanitizer Lotion lotion Canada
Soft Care 2% Chg Antimicrobial Skin Cleanser liquid Canada
Solunet C Brosse 4% liquid; sponge Canada
Soluprep solution Canada
Soluprep Antiseptic Skin Cleanser sponge Canada
Soluprep Antiseptic Skin Cleanser Preoperative Kit aerosol Canada
Soluprep Applicator solution Canada
Soluprep Aq solution Canada
Soluprep Aq Applicator solution Canada
Soluprep Aq Sponge sponge Canada
Soluprep Aq Swab swab Canada
Soluprep Aq Wipe wipe Canada
Soluprep Ld Sponge sponge Canada
Soluprep Qd Solution solution; sponge Canada
Soluprep Qd Swab swab Canada
Soluprep Qd Wipe wipe Canada
Soluprep Swab swab Canada
Soluprep Wipe wipe Canada
Spectro Gram 2 Skin Cleanser liquid Canada
Spray On Plastic Bandage Aerosol aerosol Canada
Spray On Plastic Bandage Non-aerosol spray Canada
Stanhexidine 2% With Isopropyl Alcohol 4% solution Canada
Stanhexidine 20% liquid Canada
Stanhexidine 4% With Isopropyl Alcohol 4% solution Canada
Stanhexidine Aqueous 2% With 4% Isopropyl Alcohol solution Canada
Stanhexidine Red Tincture 0.5% liquid Canada
Stat Touch 2 Antimicrobial Skin Cleanser liquid Canada
Steri-clean spray Canada
Steri-stat Liq 2.0% liquid Canada
Steri-stat Liq 20% liquid Canada
Steri-stat Liq 4.0% liquid Canada
Steri-stat Tincture (tinted) Antis Prep Gel gel Canada
Sterixin 0.05% solution Canada
Superdent Chlorhexidine Gluconate Oral Rinse liquid US
X-pur Chlorhexidine liquid Canada

Calculated Property

kind Value Source
logP 2.71 ALOGPS
logS -4.3 ALOGPS
Water Solubility 2.61e-02 g/l ALOGPS
logP 4.51 ChemAxon
IUPAC Name N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide ChemAxon
Traditional IUPAC Name chlorhexidine ChemAxon
Molecular Weight 505.447 ChemAxon
Monoisotopic Weight 504.203196424 ChemAxon
SMILES ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1 ChemAxon
Molecular Formula C22H30Cl2N10 ChemAxon
InChI InChI=1S/C22H30Cl2N10/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/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34) ChemAxon
InChIKey InChIKey=GHXZTYHSJHQHIJ-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 167.58 ChemAxon
Refractivity 181.71 ChemAxon
Polarizability 54.6 ChemAxon
Rotatable Bond Count 9 ChemAxon
H Bond Acceptor Count 10 ChemAxon
H Bond Donor Count 10 ChemAxon
pKa (strongest basic) 10.52 ChemAxon
Physiological Charge 4 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Bacteria

Target within organism

  • Bacterial outer membrane : in