Identification

Name
Chlorhexidine
Accession Number
DB00878  (APRD00545)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

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

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Chlorhexidine acetate5908ZUF22Y56-95-1WDRFFJWBUDTUCA-UHFFFAOYSA-N
Chlorhexidine gluconateMOR84MUD8E18472-51-0KUXUALPOSMRJSW-IFWQJVLJSA-N
Chlorhexidine hydrochlorideE64XL9U38K3697-42-5WJLVQTJZDCGNJN-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiseptic Skin CleanserSolution4 g/100mLTopicalCardinal Health2012-01-01Not applicableUs
ChlorhexidineSolution0.12 %BuccalEuro Pharm International Canada IncNot applicableNot applicableCanada
Chlorhexidine Alcohol FreeSolution0.12 %BuccalEuro Pharm International Canada IncNot applicableNot applicableCanada
Chlorhexidine Gluconate 0.12% Oral Rinse, USPMouthwash0.12 %OralSage Pharmaceuticals, Inc.2016-02-03Not applicableCanada
Chlorhexidine Gluconate 0.12% Oral Rinse, USPLiquid; Mouthwash0.12 %OralXttrium Laboratories, Inc.Not applicableNot applicableCanada
Chlorhexidine Gluconate Oral RinseLiquid; Mouthwash0.12 %OralColgate PalmoliveNot applicableNot applicableCanada
Denti-care Chlorhexidine Gluconate Oral Rinse 0.12%Mouthwash0.12 %Buccal; OralAmd Medicom Inc1999-11-26Not applicableCanada
E-Z Scrub 107Sponge4 %TopicalBecton DickinsonNot applicableNot applicableCanada
Gum ParoexMouthwash0.12 %BuccalSunstar Americas2012-10-01Not applicableCanada
Oro ClearMouthwash0.12 %BuccalGermiphene Corporation2016-01-25Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acclean Chlorhexidine Gluconate 0.12% Oral RinseLiquid1.2 mg/mLOralHenry Schein2009-04-01Not applicableUs
Acclean Chlorhexidine Gluconate 0.12% Oral RinseLiquid1.2 mg/mLOralHenry Schein2013-02-01Not applicableUs
Apo-chlorhexidine Oral RinseLiquid0.12 %OralApotex Corporation2000-08-29Not applicableCanada
Chlorhexidine GluconateRinse1.2 mg/mLOralXttrium Laboratories, Inc.2009-07-25Not applicableUs
Chlorhexidine GluconateRinse1.2 mg/mLOralUnit Dose Services2009-07-25Not applicableUs
Chlorhexidine GluconateRinse.12 mg/mLOralProficient Rx LP2009-08-01Not applicableUs
Chlorhexidine GluconateLiquid.12 mg/mLOralPatterson Dental2016-01-22Not applicableUs
Chlorhexidine GluconateRinse.12 mg/mLOralAtlantic Biologicals Corps.2009-08-01Not applicableUs
Chlorhexidine GluconateRinse1.2 mg/mLOralPreferreed Pharmaceuticals Inc.2014-04-21Not applicableUs
Chlorhexidine GluconateRinse1.2 mg/mLOralDen Mat Holdings, Llc2009-06-18Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiseptic Body CleanserCloth2 %TopicalSage Pharmaceuticals, Inc.2006-02-14Not applicableCanada
Antiseptic Cleanser SolutionSolution2 %TopicalNiagara Pharmaceuticals, Inc.1996-08-202016-05-12Canada
Antiseptic First Aid SprayLiquid2 %TopicalWasip Ltd.2007-06-112016-07-14Canada
Antiseptic Lotion Soap 2%Lotion2 %TopicalGOJO Industries, Inc.1997-08-132002-09-09Canada
Antiseptic Skin CleanserLiquid4 mg/100mLTopicalKinray2013-08-03Not applicableUs
Antiseptic Skin CleanserSolution4 g/100mLTopicalMckesson Medical Surgical2017-06-01Not applicableUs
Antiseptic Skin CleanserLiquid4 mg/100mLTopicalChain Drug Consortium2012-10-30Not applicableUs
Antiseptic Skin CleanserLiquid4 mg/100mLTopicalAmerisource Bergen Drug Corportaion2013-04-01Not applicableUs
Antiseptic Skin CleanserLiquid4 mg/100mLTopicalMeijer Distribution2014-01-01Not applicableUs
Antiseptic Skin CleanserLiquid4 mg/100mLTopicalMc Kesson2014-02-20Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antibacterial Protective HandLotion.07075 g/14.15gTopicalHANOVER PEN CORP dba HPC Global2013-02-01Not applicableUs
Antibacterial Protective HandLotion.0045 g/.9gTopicalHANOVER PEN CORP dba HPC Global2013-02-01Not applicableUs
Antiseptic Cleansing WipesSwab.0002 mg/mgTopicalGuangdong Comfort Medical Products Co., Ltd.2017-07-17Not applicableUs
Antiseptic Cleansing WipesSwab.0002 mg/mgTopicalFoshan Flying Medical Products Co., Ltd.2012-12-27Not applicableUs
Ezy-TMCloth2 g/100gTopicalJiangxi Sencen Hygienic Products Co., Ltd.2011-07-122016-10-13Us
KleerSightConcentrate2.36 mL/236mLIrrigationBradley Fixtures Corporation2010-03-11Not applicableUs
Oris ChxRinse1.2 mg/mLDentalDentsply Professional1999-01-01Not applicableUs
SerdaenSoap24 mg/3gTopicalBrowne Hansen Llc2013-06-01Not applicableUs
SerdaenSoap48 mg/3gTopicalBrowne Hansen Llc2013-06-01Not applicableUs
International/Other Brands
Cida-Stat (Ecolab) / Corsodyl (GlaxoSmithKline) / Dyna-Hex (Xttrium) / Exidine (Xttrium) / Hexadol (Green Cross) / Hibiscrub (AstraZeneca) / Hibispray / Hibitane (Imperial Chemical Industries) / Microderm (Johnson & Johnson) / Oro-Clense (Germiphene) / Periogard Oral Rinse (Colgate) / Pharmaseal Scrub Care (CareFusion) / Prevacare R (Johnson & Johnson) / Rotersept (Roter) / Sterilon (Emcure) / Tubulicid
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
3M AvagardChlorhexidine gluconate (8.3 mg/mL) + Ethanol (506.3 mg/mL)LotionTopical3 M Pharmaceuticals2001-06-14Not applicableUs
3m Soluprep SpongeChlorhexidine gluconate (2 %) + Isopropyl Alcohol (70 %)SpongeTopical3 M Pharmaceuticals2013-09-11Not applicableCanada
Avagard ChgChlorhexidine gluconate (1 %) + Ethanol (61 %)LotionTopical3 M Pharmaceuticals2003-07-02Not applicableCanada
Baxedin 2% - 70%Chlorhexidine gluconate (2 %) + Isopropyl Alcohol (70 %)SolutionTopicalOmega Laboratories Ltd2004-07-07Not applicableCanada
BioprepChlorhexidine gluconate (1 %) + Didecyldimethylammonium chloride (.5 %)SoapTopicalLarose & Fils Ltee1984-12-312005-03-23Canada
BioprepChlorhexidine gluconate (1 %) + Didecyldimethylammonium chloride (.5 %)SoapTopicalProduits Sani Professionel Ltee1984-12-311996-09-09Canada
Bioprep LiqChlorhexidine gluconate (.1 %) + Didecyldimethylammonium chloride (.5 %) + Isopropyl Alcohol (5 %)LiquidTopicalJ.C. Sani Care Inc.1992-12-311997-08-14Canada
Burn O Sol SprayChlorhexidine acetate (.5 %) + Benzocaine (2 %)SprayTopicalProtector Canada Inc.1992-12-312012-06-18Canada
Chlora-cleanzeChlorhexidine gluconate (20 mg/mL) + Isopropyl Alcohol (.7 mL/mL)SwabTopicalBiotronix Healthcare Industries, Inc.2017-04-18Not applicableUs
Chloraprep Liq 0.5%Chlorhexidine gluconate (0.5 %) + Isopropyl Alcohol (70 %)LiquidTopicalMedi Flex Inc.1994-12-311998-09-09Canada
Categories
UNII
R4KO0DY52L
CAS number
55-56-1
Weight
Average: 505.447
Monoisotopic: 504.203196424
Chemical Formula
C22H30Cl2N10
InChI Key
GHXZTYHSJHQHIJ-UHFFFAOYSA-N
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)
IUPAC Name
N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
SMILES
ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1

Pharmacology

Indication

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.

Structured Indications
Not Available
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.

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.

TargetActionsOrganism
ABacterial outer membrane
incorporation into and destabilization
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.

Volume of distribution
Not Available
Protein binding

87%

Metabolism
Not Available
Route of elimination

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.

Half life
Not Available
Clearance
Not Available
Toxicity

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)

Affected organisms
  • Bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not Available

References

Synthesis Reference

Rose, F.L. and Swain, G.; US. Patent 2,684,924; July 27, 1954; assigned to Imperial Chemical Industries, Ltd.

US2684924
General References
  1. McBain AJ, Bartolo RG, Catrenich CE, Charbonneau D, Ledder RG, Gilbert P: Effects of a chlorhexidine gluconate-containing mouthwash on the vitality and antimicrobial susceptibility of in vitro oral bacterial ecosystems. Appl Environ Microbiol. 2003 Aug;69(8):4770-6. [PubMed:12902270]
External Links
Human Metabolome Database
HMDB15016
KEGG Drug
D07668
KEGG Compound
C06902
PubChem Compound
9552079
PubChem Substance
46506388
ChemSpider
2612
BindingDB
50170723
ChEBI
3614
ChEMBL
CHEMBL790
Therapeutic Targets Database
DAP001326
PharmGKB
PA164776863
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chlorhexidine
ATC Codes
S03AA04 — ChlorhexidineD08AC02 — ChlorhexidineS01AX09 — ChlorhexidineS02AA09 — ChlorhexidineR02AA05 — ChlorhexidineD08AC52 — Chlorhexidine, combinationsD09AA12 — ChlorhexidineB05CA02 — ChlorhexidineA01AB03 — Chlorhexidine
AHFS Codes
  • 34:00.00 — Dental Agents
  • 52:04.92 — Miscellaneous Anti-infectives
  • 84:04.92 — Miscellaneous Local Anti-infectives
FDA label
Download (56 KB)
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingBasic ScienceCleaning Product Causing Toxic Effect1
0Not Yet RecruitingTreatmentPostoperative Flare up1
1CompletedNot AvailableSurgical Site Infections2
1CompletedPreventionPneumonia / Respiratory Tract Infections (RTI)1
1CompletedSupportive CareHead and Neck Carcinoma1
1CompletedTreatmentDentist-Patient Relations1
1RecruitingOtherChlorhexidine Allergy / Infection NOS / Rash1
1Unknown StatusPreventionDental Decay / Orthodontic Appliance Complication1
1, 2CompletedNot AvailableTopical Antisepsis1
1, 2CompletedPreventionDental Plaque1
1, 2CompletedTreatmentHealthy Volunteers3
1, 2Not Yet RecruitingPreventionBone Loss / Implant Infection1
2Active Not RecruitingTreatmentCystic Fibrosis (CF)1
2CompletedBasic ScienceStaining Effect of Chlorhexidine1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentCystic Fibrosis (CF) / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
2CompletedTreatmentDental Plaque1
2CompletedTreatmentGingival Inflammation1
2CompletedTreatmentGingival Inflammation / Mucositis1
2CompletedTreatmentHypochlorous Acid / Mouthwashes1
2CompletedTreatmentMRSA-Colonization1
2CompletedTreatmentMucositis1
2CompletedTreatmentPeri-Implantitis1
2CompletedTreatmentPeriodontitis1
2CompletedTreatmentPeriodontitis / Premature Birth of Newborn1
2RecruitingPreventionS. Aureus Oropharyngeal Colonization1
2RecruitingPreventionSurgical Site Infections1
2RecruitingPreventionVentilator-Associated Pneumonia (VAP)1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedPreventionHospital Acquired Infections / Respiratory Tract Infections (RTI) / Surgical Site Infections1
2, 3CompletedPreventionSepsis1
2, 3CompletedTreatmentCatheterization1
2, 3Not Yet RecruitingTreatmentPeriapical Abscess1
2, 3WithdrawnPreventionNeonatal Mortality Rate / Neonatal Sepsis1
3Active Not RecruitingSupportive CareInfections caused by penicillinase-producing staphylococci / Infections, Bacterial / Neoplasms, Benign / Neoplasms, Malignant / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Untreated Childhood Myeloid Neoplasm1
3CompletedNot AvailableHealthy Volunteers1
3CompletedNot AvailableTopical Antisepsis1
3CompletedDiagnosticGynecologic Diseases1
3CompletedPreventionDental Decay1
3CompletedPreventionDental Plaque1
3CompletedPreventionGeneral Surgery1
3CompletedPreventionGeneral Surgery / Irritation Potential1
3CompletedPreventionInfection NOS1
3CompletedPreventionMethicillin Resistant Staphylococcus Aureus Skin Infections1
3CompletedPreventionOmphalitis1
3CompletedPreventionSurgical Site Infections1
3CompletedPreventionSurgical Skin Preparation2
3CompletedPreventionVentilator-associated Bacterial Pneumonia1
3CompletedTreatmentDental Plaque2
3CompletedTreatmentGeneralized Adult Periodontitis1
3CompletedTreatmentGingival Diseases1
3CompletedTreatmentGingival Inflammation1
3CompletedTreatmentInfections and Respiratory Infectious1
3CompletedTreatmentPharyngitis1
3Not Yet RecruitingPreventionDental Decay1
3RecruitingPreventionInfections, Bacterial1
3RecruitingTreatmentGingival Inflammation1
3RecruitingTreatmentPeri-Implantitis1
3Unknown StatusPreventionCord Care / Neonatal Mortality / Omphalitis1
3Unknown StatusPreventionInfant, Newborn, Diseases / Puerperal Infection / Sepsis1
3Unknown StatusPreventionPeristomal Wound Infection / Swallowing Disorders1
3Unknown StatusTreatmentDental Plaque / Gingival Inflammation / Inflammatory Reaction / Periodontitis1
4Active Not RecruitingTreatmentMRSA1
4CompletedNot AvailableAntimicrobial Effectiveness2
4CompletedNot AvailableThis Study Evaluated the Effectiveness of Chlorhexidine Mouthrinse on Subgingival Microbiota1
4CompletedPreventionBacteremia1
4CompletedPreventionBacteremia / Tooth Extraction Status Nos1
4CompletedPreventionCutaneous Abscess1
4CompletedPreventionDental Decay / Periodontal Diseases1
4CompletedPreventionHealthcare-Associated Pneumonia / Hospital-acquired bacterial pneumonia / Pneumonia, Aspiration / Ventilator-Associated Pneumonia (VAP)1
4CompletedPreventionMouthwash / Oral Biofilm / Periodontitis1
4CompletedPreventionNeonatal Infections1
4CompletedPreventionPeritoneal Dialysis Catheter Exit Site Infection1
4CompletedSupportive CareGingival Inflammation1
4CompletedSupportive CareOral Mucositis1
4CompletedTreatmentDental Implants / Tooth Socket1
4CompletedTreatmentDiabetes / Periodontitis1
4CompletedTreatmentNeoplasms, Hepatic1
4CompletedTreatmentPeri-Implantitis1
4CompletedTreatmentRecession, Gingival2
4Not Yet RecruitingPreventionDental Plaque1
4RecruitingOtherSurgical Preparation of the Vagina1
4RecruitingPreventionHospitalization / Infection NOS1
4RecruitingPreventionNeoplasms, Breast / Wound Infections1
4RecruitingTreatmentInfections, Bacterial1
4RecruitingTreatmentMRSA - Methicillin Resistant Staphylococcus Aureus Infection / Skin and Subcutaneous Tissue Bacterial Infections / Staphylococcus Aureus1
4RecruitingTreatmentMechanical Ventilation for More Than 48 Hours1
4RecruitingTreatmentPeriimplantitis1
4TerminatedTreatmentMRSA - Methicillin Resistant Staphylococcus Aureus Infection / MRSA Colonization1
4TerminatedTreatmentPeriodontitis1
4Unknown StatusBasic ScienceGingival Inflammation / Oral Biofilm / Periodontitis1
4Unknown StatusPreventionBacteriuria / Hospital Acquired Infections / Urinary Tract Infections (UTIs)1
4Unknown StatusPreventionSkin Diseases, Infectious1
4Unknown StatusTreatmentAmputation Wound / Wound Infections1
Not AvailableActive Not RecruitingTreatmentAdenocarcinoma Of Esophagus / Esophagus, Barrett / Reflux Esophagitis (RE)1
Not AvailableCompletedNot AvailableChronic Periodontitis1
Not AvailableCompletedNot AvailableDrying Time1
Not AvailableCompletedNot AvailableRespiratory Failure / Ventilator-Associated Pneumonia (VAP) / Wounds and Injuries1
Not AvailableCompletedPreventionAsepsis / Lumbar epidural anesthesia / Lumbar epidural anesthesia therapy1
Not AvailableCompletedPreventionBacteremia2
Not AvailableCompletedPreventionCaries / Dental Plaque / Oral Surgical Wound Infection / Periimplantitis / Periodontal Diseases1
Not AvailableCompletedPreventionCatheter-Related Infections / Cross Infection / Infection Due to Indwelling Urinary Catheter / Infection, Postoperative Wound / Ventilator-Associated Pneumonia (VAP)1
Not AvailableCompletedPreventionGingival Inflammation1
Not AvailableCompletedPreventionInfection NOS1
Not AvailableCompletedPreventionInfection caused by staphylococci1
Not AvailableCompletedPreventionLow Birth Weight / Neonatal Sepsis1
Not AvailableCompletedPreventionMRSA Skin Infections / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedPreventionNeonatal Mortality / Neonatal Sepsis1
Not AvailableCompletedPreventionSurgical Site Infection Following Cesarean Delivery1
Not AvailableCompletedPreventionTracheal Intubation1
Not AvailableCompletedTreatmentAbscesses / Furunculosis / MRSA Infection / Staphylococcal Skin Infections / Staphylococcus Aureus1
Not AvailableCompletedTreatmentBreath odour1
Not AvailableCompletedTreatmentChronic Periodontitis / Periodontal Diseases1
Not AvailableCompletedTreatmentContraception1
Not AvailableCompletedTreatmentGingival Inflammation1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
Not AvailableCompletedTreatmentMRSA Colonization1
Not AvailableCompletedTreatmentOral Cancers / Oral Mucositis1
Not AvailableCompletedTreatmentVentilator-associated Bacterial Pneumonia1
Not AvailableNot Yet RecruitingBasic ScienceOral Salivary Streptococcus Mutans Counts1
Not AvailableNot Yet RecruitingTreatmentGingival Hemorrhage1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingPreventionShoulder Infection1
Not AvailableRecruitingPreventionStaph Aureus Colonization / Staph Aureus Infection1
Not AvailableRecruitingPreventionSurgical Site Infections2
Not AvailableUnknown StatusPreventionCentral Line-associated Bloodstream Infection (CLABSI) / Line Insertion Site1
Not AvailableUnknown StatusPreventionLine Insertion Site1
Not AvailableUnknown StatusTreatmentHypertensive / Periodontitis1
Not AvailableWithdrawnPreventionInfection NOS1

Pharmacoeconomics

Manufacturers
  • Xttrium laboratories inc
  • Sage products inc
  • Actavis mid atlantic llc
  • Hi tech pharmacal co inc
  • John o butler co
  • Novex pharma
  • Teva pharmaceuticals usa inc
  • Wockhardt eu operations (swiss) ag
  • 3m co
  • Colgate oral pharmaceuticals inc
  • Soapco inc
  • Ecolab inc
  • Regent medical americas llc
  • Johnson and johnson medical inc
  • Matrix medical corp
  • Kw griffen co
  • Becton dickinson and co
  • Kendall co
  • Becton dickinson surgical system
  • Molnlycke health care
  • Pharmaseal div baxter healthcare corp
  • Dexcel pharma technologies ltd
Packagers
Dosage forms
FormRouteStrength
SpongeTopical
LiquidOral1.2 mg/mL
LotionTopical.0045 g/.9g
LotionTopical.07075 g/14.15g
ClothTopical2 %
SwabTopical.0002 mg/mg
SolutionTopical4 g/100mL
SolutionTopical2 g/100g
LiquidOral0.12 %
LotionTopical
DressingTopical.5 %
SpongeTopical40 mg/mL
SolutionTopical20 mg/mL
SolutionTopical40 mg/mL
SolutionTopical.5 %
SolutionTopical40 g/1000mL
SolutionTopical.04 mg/mL
SprayTopical
SolutionTopical4 %
ClothTopical500 mg/1
LiquidOral.12 mg/mL
RinseOral.12 mg/mL
RinseOral1.2 mg/mL
LiquidBuccal1.2 [iU]/mL
Liquid; mouthwashOral0.12 %
MouthwashOral0.12 %
SolutionTopical0.05 %
SolutionTopical20 %
LiquidTopical.05 %
LiquidDental.12 g/mL
LotionTopical4 %
LiquidTopical2 g/100mL
LiquidTopical4 g/100mL
LiquidTopical4.0 %
LiquidTopical2 %
LiquidOphthalmic
ClothTopical2 g/100g
CreamTopical
GelTopical2 %
GelTopical
MouthwashBuccal0.12 %
ClothTopical
LiquidTopical
GelTopical4 %
AerosolTopical
SolutionTopical213 g/1000mL
ConcentrateIrrigation2.36 mL/236mL
CreamTopical2 %
SwabTopical2 %
Kit
RinseDental1.2 mg/mL
OintmentTopical1 %
Liquid; mouthwashBuccal0.12 %
Insert, extended releasePeriodontal2.5 mg/1
MouthwashBuccal; Oral0.12 %
RinseBuccal1.2 mg/mL
SolutionBuccal0.12 %
LiquidTopical.12 %
SolutionOphthalmic
SolutionTopical1 mg/25mL
SolutionTopical
Kit; solutionDental10 %
LiquidBuccal0.12 %
LotionTopical2 %
SolutionTopical.75 mg/100mL
SolutionTopical4 mg/100mL
LiquidTopical4 mg/100mL
SolutionTopical2 g/100mL
SolutionTopical2 mg/100mL
LiquidTopical4 %
SoapTopical
LotionTopical2.0 %
SoapTopical24 mg/3g
SoapTopical48 mg/3g
Kit
LotionTopical2.25 %
Liquid; spongeTopical4 %
SpongeTopical4 %
AerosolTopical4 %
SolutionTopical2 %
SpongeTopical2 %
SpongeTopical0.05 %
Solution; spongeTopical
SwabTopical
ShampooTopical
AerosolTopical0.5 %
SprayTopical0.5 %
LiquidTopical.5 %
SprayTopical2 %
LiquidTopical20 %
LiquidDental.12 g/100mL
Prices
Unit descriptionCostUnit
Peridex 0.12% Solution 473ml Bottle23.99USD bottle
Periogard 0.12% Solution 473ml Bottle15.99USD bottle
Chlorhexidine Gluconate 0.12% Solution 473ml Bottle14.0USD bottle
Biopatch dressing4.21USD each
Hibistat towelette0.43USD each
Chlorhexidine gluc 20% soln0.16USD ml
Hibiclens 4% liquid0.04USD ml
Peridex 0.12% liquid0.04USD ml
Chlorhexidine 2% scrub0.03USD ml
Chlorhexidine 0.12% rinse0.02USD ml
Dynahex 4% liquid0.02USD ml
Dynahex 2% liquid0.01USD ml
Periogard 0.12% oral rinse0.01USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7422388No2007-04-252027-04-25Us
US6536975No2000-11-102020-11-10Us
US6729786No2003-03-142023-03-14Us
US7241065No2003-03-142023-03-14Us
US5690958No1996-09-302016-09-30Us
US6991394No2004-01-312024-01-31Us
US7182536No2003-12-302023-12-30Us
US5538353No1995-08-252015-08-25Us
US5772346No1997-04-222017-04-22Us
US7081246No1996-08-032016-08-03Us
US5897031No1996-06-212016-06-21Us
USD468424No1997-01-072017-01-07Us
US7066916No2004-02-172024-02-17Us
US7595021No2003-05-122023-05-12Us
US7717889No2005-02-272025-02-27Us
US7935093No2007-10-022027-10-02Us
US7427574No2006-04-252026-04-25Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)258-260Rose, F.L. and Swain, G.; US. Patent 2,684,924; July 27, 1954; assigned to Imperial Chemical Industries, Ltd.
water solubility800 mg/L (at 20 °C)MERCK INDEX (1996)
logP0.08HANSCH,C ET AL. (1995), ionized pH 5
pKa10.8 (at 25 °C)HANSCH,C & LEO,AJ (1985)
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 Count9ChemAxon
Refractivity181.71 m3·mol-1ChemAxon
Polarizability54.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8984
Blood Brain Barrier+0.7872
Caco-2 permeable+0.5231
P-glycoprotein substrateSubstrate0.6016
P-glycoprotein inhibitor INon-inhibitor0.5733
P-glycoprotein inhibitor IIInhibitor0.9175
Renal organic cation transporterInhibitor0.7955
CYP450 2C9 substrateNon-substrate0.7033
CYP450 2D6 substrateNon-substrate0.6218
CYP450 3A4 substrateNon-substrate0.6532
CYP450 1A2 substrateInhibitor0.8025
CYP450 2C9 inhibitorNon-inhibitor0.6847
CYP450 2D6 inhibitorInhibitor0.927
CYP450 2C19 inhibitorNon-inhibitor0.5065
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.59
Ames testNon AMES toxic0.6532
CarcinogenicityNon-carcinogens0.857
BiodegradationNot ready biodegradable0.9896
Rat acute toxicity1.7711 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5579
hERG inhibition (predictor II)Non-inhibitor0.5661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ufr-2900000000-77fb2c1a85c1b39d8e91
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00yi-2912000000-109a5810a9e5d36f3105

Taxonomy

Description
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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Chlorobenzenes
Alternative Parents
Biguanides / Aryl chlorides / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Organochlorides / Imines / Hydrocarbon derivatives
Substituents
Biguanide / Chlorobenzene / Aryl chloride / Aryl halide / Guanidine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Organohalogen compound / Imine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monochlorobenzenes, biguanides (CHEBI:3614)

Targets

1. Bacterial outer membrane
Kind
Group
Organism
Not Available
Pharmacological action
Yes
Actions
Incorporation into and destabilization
References
  1. Zorko M, Jerala R: Alexidine and chlorhexidine bind to lipopolysaccharide and lipoteichoic acid and prevent cell activation by antibiotics. J Antimicrob Chemother. 2008 Oct;62(4):730-7. doi: 10.1093/jac/dkn270. Epub 2008 Jul 16. [PubMed:18635521]
  2. Kuyyakanond T, Quesnel LB: The mechanism of action of chlorhexidine. FEMS Microbiol Lett. 1992 Dec 15;100(1-3):211-5. [PubMed:1335944]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Histamine n-methyltransferase activity
Specific Function
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name
HNMT
Uniprot ID
P50135
Uniprot Name
Histamine N-methyltransferase
Molecular Weight
33294.765 Da
References
  1. Harle DG, Baldo BA: Structural features of potent inhibitors of rat kidney histamine N-methyltransferase. Biochem Pharmacol. 1988 Feb 1;37(3):385-8. [PubMed:3337739]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Chloramphenicol o-acetyltransferase activity
Specific Function
This enzyme is an effector of chloramphenicol (Cm) resistance in bacteria. Acetylates Cm but not 1-acetoxy-Cm.
Gene Name
cat
Uniprot ID
P26841
Uniprot Name
Chloramphenicol acetyltransferase
Molecular Weight
23524.385 Da
References
  1. Solov'eva NN, Belousova II, Tereshin IM: [Effect of biologically active substances on Escherichia coli chloramphenicol acetyltransferase activity]. Antibiotiki. 1979 Jun;24(6):436-40. [PubMed:378112]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13