N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide

• ChemBase ID: 756
• Molecular Formular: C22H30Cl2N10
• Molecular Mass: 505.4466
• Monoisotopic Mass: 504.20319637
• SMILES: c1(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(cc2)Cl)ccc(cc1)Cl
• Canonical SMILES: N=C(NC(=N)Nc1ccc(cc1)Cl)NCCCCCCNC(=N)NC(=N)Nc1ccc(cc1)Cl
• 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)
• InChIKey: GHXZTYHSJHQHIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
• IUPAC Traditional name: chlorhexidine hydrochloride; chlorhexidine
• Brand Name: Bioscrub; Brian Care; Cida-Stat; Dyna-Hex; Exidine; Fimeil; Hexadol; Hibiclens; Hibidil; Hibiscrub; Hibisol; Hibispray; Hibistat; Hibitane; Microderm; Nolvasan; Oro-Clense; Peridex; Periochip; Periogard; Pharmaseal Scrub Care; Prevacare R; Rotersept; Savloclens; Savlon Babycare; Sodium Houttuyfonamide; Soretol; Steri-Stat; Sterido; Sterilon; Superspray; Tubulicid
• Synonyms: N,N’’-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide Dihydrochloride; Lisium; Chlorhexidine Dihydrochloride; Chlorhexidin [Czech]; Chlorhexidine Base; Chlorhexidine Gluconate; Chlorhexidinum [INN-Latin]; Cloresidina [DCIT]; Clorhexidina [INN-Spanish]; Decanoylacetaldehyde Sodium Sulfide; Chlorhexidine; 1,1′-Hexamethylenebis[5-(4-chlorophenyl)biguanide]; Chlorhexidine; 1,1'-己基双[5-(对氯苯基)双胍]; 氯己定

Database IDs

• CAS Number: 3697-42-5; 55-56-1
• EC Number: 200-238-7
• MDL Number: MFCD00009673
• Beilstein Number: 2826432
• PubChem SID: 24857031; 160964219; 24854905; 24861545
• PubChem CID: 9552079

CALCULATED PROPERTIES

JChem

• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): -4.561288
• LogD (pH = 7.4): -1.3018613
• Log P: 4.5103693
• Molar Refractivity: 181.7146 cm^3
• Polarizability: 51.81197 Å^3
• Polar Surface Area: 167.58 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.71
• LOG S: -4.29
• Solubility (Water): 2.61e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.08%(w/v); DMSO; Water
• Apperance: White Solid
• Melting Point: 134-136 °C; 134-136 °C(lit.); 260-262°C (dec)
• Hydrophobicity(logP): 3

Safety Information

• Storage Condition: Refrigerator
• RTECS: DU1925000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-43-50/53
• Safety Statements: 26-36/37-60-61
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H334-H335-H410
• GHS Precautionary statements: P261-P273-P305 + P351 + P338-P342 + P311-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥99.0% (HPLC); ≥99.5%; 98%
• Grade: purum
• Impurities: <1.0% water
• Linear Formula: [-(CH2)3NHC(=NH)NHC(=NH)NHC6H4Cl]2

DETAILS

DrugBank - DB00878

• Drug Groups: approved
• Description: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque. [PubChem]
• 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.
• Pharmacology: 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.
• 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
• 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: 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.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 348031

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 282227

Application
Analytical standard for pharmaceuticals.
Packaging
1 g in glass bottle
5 g in poly bottle

Toronto Research Chemicals - C335050

It is a bisbiguanide with bacteriostatic activity. Antiseptic; disinfectant.

REFERENCES

• Davies, G.E., et al.: Br. J. Pharmacol., 9, 192 (1954)
• Foulkes, D.M., et al.: J. Periodontal Res., 8, 55 (1954)