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

• ChemBase编号: 756
• 分子式: C22H30Cl2N10
• 平均质量: 505.4466
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
• IUPAC传统名: chlorhexidine hydrochloride; chlorhexidine
• 商标名: 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
• 别名: 1,1'-己基双[5-(对氯苯基)双胍]; 氯己定; 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

登记号

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

理论计算性质

JChem

• 质子受体: 10
• 质子供体: 10
• LogD (pH = 5.5): -4.561288
• LogD (pH = 7.4): -1.3018613
• Log P: 4.5103693
• 摩尔折射率: 181.7146 cm^3
• 极化性: 51.81197 Å^3
• 极化表面积: 167.58 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 2.71
• LOG S: -4.29
• 溶解度: 2.61e-02 g/l

分子性质

理化性质

• 溶解度: 0.08%(w/v); DMSO; Water
• 外观: White Solid
• 熔点: 134-136 °C; 134-136 °C(lit.); 260-262°C (dec)
• 疏水性(logP): 3

安全信息

• 保存条件: Refrigerator
• RTECS编号: DU1925000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 36/37/38-43-50/53
• 安全公开号: 26-36/37-60-61
• GHS危险品标识: GHS07; GHS08; GHS09
• GHS警示词: Danger
• GHS危险声明: H315-H319-H334-H335-H410
• GHS警示性声明: P261-P273-P305 + P351 + P338-P342 + P311-P501
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

产品相关信息

• 纯度: ≥99.0% (HPLC); ≥99.5%; 98%
• 级别: purum
• 杂质: <1.0% water
• 线性分子式: [-(CH2)3NHC(=NH)NHC(=NH)NHC6H4Cl]2

详细说明

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

包装
25, 100 g in glass bottle

Sigma Aldrich - 282227

Application
药物分析标准品。
包装
1 g in glass bottle
5 g in poly bottle

Toronto Research Chemicals - C335050

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

参考文献

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