5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide
chlorhexidine
CAS: 55-56-1
Molecular Formula: C22H30Cl2N10
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide - Names and Identifiers
| Name | chlorhexidine |
| Synonyms | fimeil hexadol chlorhexidin chlorhexidine Chlor hexidine Chlorhexidine Base Chlorohexidine base chlorocyclohexatriene 1,6-bis(p-chlorophenyldiguanido)hexane 1,6-di(4'-chlorophenyldiguanido)hexane 1,6-bis(5-(p-chlorophenyl)biguandino)hexane 1,1'-hexamethylenebis(5-(p-chlorophenyl)-biguanid 5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide 2,4,11,13-tetraazatetradecanediimidamide,n,n''-bis(4-chlorophenyl)-3,12-diim |
| CAS | 55-56-1 |
| EINECS | 200-238-7 |
| 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 |
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide - Physico-chemical Properties
| Molecular Formula | C22H30Cl2N10 |
| Molar Mass | 505.45 |
| Density | 1.1555 (rough estimate) |
| Melting Point | 134-136 °C (lit.) |
| Boling Point | 641.45°C (rough estimate) |
| Flash Point | 27.987°C |
| Water Solubility | 0.08 g/100 mL (20 ºC) |
| Solubility | water: soluble0.08% at 20°C |
| Vapor Presure | 13.402mmHg at 25°C |
| Appearance | White powder |
| Merck | 13,2108 |
| BRN | 2826432 |
| pKa | pKa 10.78 (Uncertain) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.6300 (estimate) |
| MDL | MFCD00009673 |
| Physical and Chemical Properties | Melting Point: 132-136°C Boiling Point: 127.658°C at 760 mmHg flash point: 27.987°C water solubility: 0.08g/100 mL (20°C) |
| Use | For the surface active form of fungicides, with a strong broad-spectrum antibacterial, bactericidal effect, gram-positive bacteria and negative bacteria are effective |
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R43 - May cause sensitization by skin contact R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| RTECS | DU1925000 |
| FLUKA BRAND F CODES | 10-34 |
| HS Code | 29215900 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 5000 mg/kg |
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide - Reference
| Reference Show more | 1. Dong Sheng LIANG, LI Huanying LI, Xiao Hu XU, et al. Design, screening and evaluation of antimicrobial activity of polypeptides against Streptococcus mutans [J]. Journal of Southern Medical University, 2019, 39(7). 2. Feng, Xiao, et al. "Equilibrum solution, solvent effect and preferred solution of chlorhexidine in aquatic co-solvent solutions of (methanol, ethanol, N, N-dimethylformamide and 1, 4-dioxane)." The Journal of Chemical Thermodynamics 129 (2019): 148- |
5,5-bis(4-chlorophenyl)-1,1-hexamethylenedibiguanide - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| pharmacological effects | chlorhexidine, also known as chlorhexidine, is a cationic surfactant with a strong broad-spectrum antibacterial and bactericidal effects. it is a good bactericidal and disinfectant, and has a stronger antibacterial effect on gram-positive and negative bacteria than benzalkonium bromide. It is positively charged, and it is adsorbed on the surface of the negatively charged plaque and oral mucosa when the mouth is gargled, and then the adsorbed drug is dispersed from these parts, and gradually precipitated to produce a continuous effect, until the concentration in the saliva decreases after 24 hours. The product is adsorbed on the osmotic barrier of the bacterial cytoplasmic membrane, causing the cell contents to leak out, showing antibacterial effect at low concentration, and bactericidal effect at high concentration. It is still effective even when there is serum, blood, etc. Not effective against spores, acid-fast bacilli, fungi and viruses. It is clinically used for washing hands before surgery, soaking hands, skin disinfection in the operation area; oral cavity, throat infection, wound flushing, instrument disinfection, ward or operating room and other environmental disinfection. Cream or ointment for infantile eczema, small area burns, scalds and impetigo; powder for prickly heat, eczema dermatitis erythema stage. The coating is used for mild burns and scalds. Chlorhexidine is combined with hydrochloric acid, acetic acid, and gluconic acid to form salts to form chlorhexidine hydrochloride, chlorhexidine acetate and chlorhexidine gluconate respectively. At present, chlorhexidine acetate is commonly used clinically in China, but chlorhexidine gluconate is mainly used clinically in the United States and Europe. Especially in the last 10 years, international research reports on chlorhexidine mainly focus on chlorhexidine gluconate. Chlorhexidine hydrochloride has low solubility in water, and its preparation is mainly ointment and film coating agent, which has been basically eliminated in actual use. |
| Physical and chemical properties | Chlorhexidine, the chemical name is 1,6-bis (n-p-chlorobenzene biguanide) hexane, also known as dichlorobenzene biguanide hexane. The so-called guanidine can be regarded as a compound formed by the substitution of the oxygen atom in the urea molecular structure (-NH-CO-NH-) by imino (= NH). The group in the guanidine molecule after removing a hydrogen atom is called guanidine group, guanidine Group is the characteristic functional group of chlorhexidine. It can be seen from the structural formula of Figure 1 that due to the presence of the imine group, chlorhexidine itself is an alkaline substance. Because it is difficult to ionize, it is difficult to dissolve in water. It can form salts with inorganic acids or organic acids. Soluble in water. Chlorhexidine reacts with different acids to obtain different salts, such as reacting with acetic acid to obtain chlorhexidine acetate (ChlorhexidineAcetate,CHA); React with hydrochloric acid to obtain chlorhexidine hydrochloride (Chlorhexidinehydrochloride); React with gluconic acid to obtain chlorhexidine gluconate (ChlorhexidineGluconate, CHG). Figure 1 shows chlorhexidine gluconate, chlorhexidine acetate and chlorhexidine hydrochloride after the structural formula of chlorhexidine gluconate is a neutral substance. Among them, chlorhexidine gluconate has the largest water solubility (20%), followed by chlorhexidine acetate (1.8%) and chlorhexidine hydrochloride (0.06%). |
| pharmacokinetics | this product is kept in the oral cavity about 30% after gargling, and then slowly released into oral saliva. Studies in humans and animals have shown that gastrointestinal absorption is very poor. After oral administration of 300mg of this product for 30 minutes, the average peak plasma concentration is 0.206 μg/g. About 90% is excreted from feces,<1% is excreted from urine, and cannot be detected in plasma after 12 hours. |
| use | for gingivitis (acute necrotizing ulcerative gingivitis), oral infections after dental surgery, prevention and treatment of oral infections in patients with cancer and leukemia, stomatitis, follicular stomatitis, and reduction of dental plaque caused by bacterial or fungal oral infections caused by denture wear. It is also used as a disinfectant for instruments and skin and as a preservative for eye drops. it is a surface active dosage form fungicide, which has quite strong broad-spectrum antibacterial and bactericidal effects, and is effective against gram-positive and negative bacteria |
| precautions | 1. avoid contact with eyes. 2. In case of cork (plug), drug activity can be lost. 3. It cannot be mixed with soap, alkali, iodine tincture, potassium permanganate, mercury oxide or washing powder. Because it has antagonistic effect with anionic surfactant, it is not suitable for sterilization. 4. It cannot be used for aseptic treatment of surgical instruments. 5. Because it cannot kill hepatitis B virus, Mycobacterium tuberculosis and spores, it cannot be used for disinfection of feces, sputum and other excreta and secretions. 6. Avoid using high-concentration drugs. 7. Allergic to this product, anterior teeth filling (permanent coloring) and periodontitis (can increase the gingival stones) disabled. Patients aged 10 to 18 years should not use gargle medicine. 8. The needle and barrel soaked with this product must be rinsed with clear water before spinal puncture. 9.1% Chlorhexidine acetate aqueous solution is unstable, white precipitate will be precipitated after being placed. Generally, acetate of this product is used to prepare ointment and gluconate can be used to prepare solution. |
| adverse reactions | occasionally can cause allergic reactions such as contact dermatitis. The high concentration solution has strong irritation to the conjunctiva, and can also soften the oral epithelium and cause ulcers. Can cause vaginal ulcer. Occasionally hematuria has been reported during bladder lavage. This product gargle can stain teeth (50%) when used in oral cavity. Heavy coloring is 10%. Among them, those with more tooth spots and precipitation are more prominent, and those with dentures can cause permanent coloring. It can also cause transient taste changes. (2016-01-22) |
| drug interaction | 1. this product has incompatibility with potassium iodide and cannot be used together. 2.3. When the concentration is above 0.05%, it shall not be compatible with borate, bicarbonate, carbonate, chloride, citrate, phosphate and sulfate, otherwise low solubility salts will be generated, and precipitation will be precipitated after 24 hours. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral administration-rat LD50: 9200 mg/kg; Oral administration-mouse LDL0: 2515 mg/kg |
| stimulation data | skin-human 1.5 mg/72 h mild |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxides, chloride smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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