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| Other Sizes |
| Targets |
Chlorobutanol acts primarily through depression of the sensory cortex, decreasing motor activity, and producing drowsiness, sedation, and hypnosis. It affects the GABAergic neurotransmission pathway by enhancing the effect of GABA, leading to chloride influx into neurons and hyperpolarization. Additionally, chlorobutanol has been found to inhibit mammalian Nav 1.2 channels at concentrations less than those used to preserve parenteral solutions. Its antimicrobial mechanism involves disruption of bacterial cell membranes and inhibition of essential metabolic processes.
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| ln Vitro |
Chlorobutanol hemihydrate demonstrates broad-spectrum antimicrobial activity in vitro against a wide variety of Gram-positive and Gram-negative bacteria, as well as several mold spores and fungi. It inhibits the aggregation and release of human platelets in vitro. The compound exhibits antibacterial and antifungal properties that make it effective as a preservative in pharmaceutical formulations. It also possesses sedative-hypnotic and weak local anesthetic actions, similar in nature to chloral hydrate.
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| ln Vivo |
In vivo, chlorobutanol hemihydrate elicits sedative-hypnotic and weak local anesthetic actions. It is active against a wide variety of bacteria and fungi in biological systems. The compound is used as an ophthalmic preservative and has been studied for its effects on the central nervous system. However, its clinical use as a sedative is limited due to its long terminal half-life and considerable accumulation following multiple dosing. It has reached a maximum clinical trial phase of IV and is indicated for nausea.
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| Enzyme Assay |
For antimicrobial susceptibility testing, chlorobutanol hemihydrate is evaluated using standard broth microdilution or agar diffusion methods against Gram-positive and Gram-negative bacteria, as well as fungal species. Serial dilutions of the compound are prepared in appropriate growth media and inoculated with standardized microbial suspensions. Minimum inhibitory concentration (MIC) values are determined after incubation. For GABAergic activity assessment, electrophysiological recordings or receptor binding assays are used to evaluate the compound's effects on GABA receptors and chloride channel function.
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| Cell Assay |
For cellular studies, various cell lines are cultured in appropriate media and treated with chlorobutanol hemihydrate at different concentrations. Antimicrobial activity is assessed using standard microbiological techniques including broth microdilution and agar diffusion methods against bacterial and fungal strains. Cytotoxicity is evaluated using mammalian cell lines with MTT or similar assays. Platelet aggregation studies are conducted using human platelets in vitro. For sedative-hypnotic activity, neuronal cell cultures or brain slice preparations may be used to assess effects on neuronal excitability and GABAergic transmission.
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| Animal Protocol |
For in vivo pharmacological studies, animal models are used to evaluate the sedative-hypnotic and anesthetic properties of chlorobutanol. Rodents are typically administered the compound via oral, intraperitoneal, or intravenous routes. Behavioral assessments including locomotor activity, righting reflex, and sedation scores are monitored. For antimicrobial efficacy, animal models of infection may be used, though chlorobutanol is primarily employed as a preservative. Toxicological studies in animals assess the compound's safety profile, accumulation potential, and organ toxicity.
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| ADME/Pharmacokinetics |
Following oral administration in healthy subjects, the plasma concentration of chlorobutanol fell by 50% within 24 hours post-administration. The mean urinary recovery accounts for 9.6%, and the volume of distribution after oral administration is approximately 233 ± 141 L. Under physiological conditions, chlorobutanol is unstable. Due to the long terminal half-life of 37 days, the use of chlorobutanol as a sedative is limited because of considerable accumulation following multiple dosing. The compound is typically administered as a preservative in topical and parenteral formulations.
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| Toxicity/Toxicokinetics |
Chlorobutanol hemihydrate is an orally toxic preservative with antimicrobial activity. It inhibits Gram-positive and Gram-negative bacteria and fungi, and inhibits the aggregation and release of human platelets in vitro. Due to its long terminal half-life of 37 days, the use of chlorobutanol as a sedative is limited because of considerable accumulation following multiple dosing. It has been found to inhibit mammalian Nav 1.2 channels at concentrations less than those used to preserve parenteral solutions. Standard safety precautions should be followed when handling this compound.
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| References |
[1]. Smoak IW, et al. Chlorobutanol: maternal serum levels and placental transfer in the mouse. Vet Hum Toxicol. 1997 Oct;39(5):287-90.
[2]. Friesen WT, et al. The antibacterial stability of chlorobutanol stored in polyethylene bottles. Am J Hosp Pharm. 1971 Jul;28(7):507-12. |
| Additional Infomation |
Chlorobutanol hemihydrate is a pharmaceutical preservative with sedative-hypnotic actions that has reached a maximum clinical trial phase of IV and is indicated for nausea. It is active against a wide variety of Gram-positive and Gram-negative bacteria, and several mold spores and fungi. The compound is widely used in food and cosmetic industries. Due to its long terminal half-life of 37 days, its use as a sedative is limited. It is also used as a chemical preservative for parenteral drugs. Chlorobutanol hemihydrate is for research and pharmaceutical use and has not been approved as a therapeutic agent for systemic indications.
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| Molecular Formula |
C4H7CL3O.1/2H2O
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|---|---|
| Molecular Weight |
186.46
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| Exact Mass |
369.923
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| CAS # |
6001-64-5
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| Related CAS # |
Chlorobutanol;57-15-8
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| PubChem CID |
5284505
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| Appearance |
White to yellow solid powder
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| Boiling Point |
167ºC
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| Melting Point |
75-79ºC
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| Flash Point |
100ºC
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| LogP |
2.063
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
17
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| Complexity |
83.8
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC(C(C([H])([H])[H])(C([H])([H])[H])O[H])(Cl)Cl
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| InChi Key |
WRWLCXJYIMRJIN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/2C4H7Cl3O.H2O/c2*1-3(2,8)4(5,6)7;/h2*8H,1-2H3;1H2
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| Chemical Name |
1,1,1-trichloro-2-methylpropan-2-ol;hydrate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 100 mg/mL (536.31 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.41 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.41 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3631 mL | 26.8154 mL | 53.6308 mL | |
| 5 mM | 1.0726 mL | 5.3631 mL | 10.7262 mL | |
| 10 mM | 0.5363 mL | 2.6815 mL | 5.3631 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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