Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C4H7Cl3O.H2O |
| Molecular Weight | 372.929 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC(C)(O)C(Cl)(Cl)Cl.CC(C)(O)C(Cl)(Cl)Cl
InChI
InChIKey=WRWLCXJYIMRJIN-UHFFFAOYSA-N
InChI=1S/2C4H7Cl3O.H2O/c2*1-3(2,8)4(5,6)7;/h2*8H,1-2H3;1H2
Chlorobutanol, or trichloro-2-methyl-2-propanol, is an analgesic and sedative hypnotic in man, and an experimental general anesthetic. It has antibacterial and antifungal properties. It is also used chemical preservative for parenteral drugs. It was found, that chlorobutanol inhibited mammalian Nav 1.2 channels at concentrations less than those used to preserve parenteral solutions. Its mechanism of inhibiting Na channels differs from that of local anesthetics in that it does not show use dependent or state dependent inhibition.
Approval Year
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7159691 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLOROBUTANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
43% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7159691 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLOROBUTANOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: Page: p.376 |
healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: Page: p.376 |
Other AEs: Sedation, Light headedness... Other AEs: Sedation Sources: Page: p.376Light headedness Euphoria |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Euphoria | 600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: Page: p.376 |
healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: Page: p.376 |
|
| Light headedness | 600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: Page: p.376 |
healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: Page: p.376 |
|
| Sedation | 600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: Page: p.376 |
healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: Page: p.376 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Is ketamine or its preservative responsible for neurotoxicity in the rabbit? | 1993 Jan |
|
| The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations. | 2000 Feb |
|
| Structural elucidation of disinfection by-products in treated drinking water. | 2001 |
|
| Quaternary ammoniums and other preservatives' contribution in oxidative stress and apoptosis on Chang conjunctival cells. | 2001 Mar |
|
| Effects of common ophthalmic preservatives on ocular health. | 2001 Sep-Oct |
|
| Clinical inquiries. What is the best treatment for impacted cerumen? | 2002 Feb |
|
| Ear drops for the removal of ear wax. | 2003 |
|
| Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. | 2003 |
|
| Review of a randomized trial comparing 2 cerumenolytic agents. | 2003 Dec |
|
| QTc interval prolongation associated with intravenous methadone. | 2003 Oct |
|
| Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes. | 2003 Sep 19 |
|
| 4-Chlorobutanol induces unusual reversible and irreversible thermal unfolding of ribonuclease A: thermodynamic, kinetic, and conformational characterization. | 2004 Apr |
|
| Neurotoxicity of intra-arterial papaverine preserved with chlorobutanol used for the treatment of cerebral vasospasm after aneurysmal subarachnoid hemorrhage. | 2004 Nov |
|
| Randomized, placebo-controlled evaluation of Cerumenex and Murine earwax removal products. | 2004 Oct |
|
| Allergic contact dermatitis from triethanolamine polypeptide oleate condensate in eardrops and shampoo. | 2005 Apr |
|
| Preventing exposure keratopathy in the critically ill: a prospective study comparing eye care regimes. | 2005 Aug |
|
| Application of a capillary electrophoresis method for simultaneous determination of preservatives in pharmaceutical formulations. | 2005 Feb |
|
| Assessment of corneal epitheliopathy in the critically ill. | 2005 Feb |
|
| An efficient synthesis of a dual PPAR alpha/gamma agonist and the formation of a sterically congested alpha-aryloxyisobutyric acid via a Bargellini reaction. | 2005 Oct 14 |
|
| Cerumen removal products. | 2005 Sep-Oct |
|
| Are multidose over-the-counter artificial tears adequately preserved? | 2006 May |
|
| Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage. | 2007 |
|
| Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
|
| [Contact allergy to triethanolamine in ear drops and shampoo]. | 2007 Jan |
|
| Effect of ophthalmic solution components on acrylic intraocular lenses. | 2007 Jan |
|
| Equimolar mixture of 2,2,2-trifluoroethanol and 4-chloro-1-butanol is a stronger inducer of molten globule state: isothermal titration calorimetric and spectroscopic studies. | 2007 Oct |
|
| Minimally invasive strabismus surgery for horizontal rectus muscle reoperations. | 2008 Dec |
|
| Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla. | 2008 Mar |
|
| Comparative toxicity of preservatives on immortalized corneal and conjunctival epithelial cells. | 2009 Apr |
|
| A Freshwater clam (Corbicula fluminea) extract reduces cholesterol level and hepatic lipids in normal rats and xenobiotics-induced hypercholesterolemic rats. | 2009 Apr 22 |
|
| Randomized, placebo-controlled evaluation of chlorobutanol, potassium carbonate, and irrigation in cerumen removal. | 2009 Aug |
|
| Atlantic salmon eggs favour sperm in competition that have similar major histocompatibility alleles. | 2009 Feb 7 |
|
| Regeneration of the radial nerve cord in the sea cucumber Holothuria glaberrima. | 2009 Jan 6 |
|
| Therapeutic approaches to cerebral vasospasm complicating ruptured aneurysm. | 2009 Nov 16 |
|
| Allergy to ophthalmic preservatives. | 2009 Oct |
|
| Interactions at human ether-à-go-go-related gene channels. | 2010 Apr |
|
| Evaluation of acute corneal barrier change induced by topically applied preservatives using corneal transepithelial electric resistance in vivo. | 2010 Jan |
|
| High gene expression of inflammatory markers and IL-17A correlates with severity of injection site reactions of Atlantic salmon vaccinated with oil-adjuvanted vaccines. | 2010 May 27 |
|
| [Chlorobutanol poisoning: about a case]. | 2010 Oct |
|
| Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines. | 2010 Sep 20 |
Sample Use Guides
It was examined chlorobutanol effect on on exocrine response and intracellular Ca2+ dynamics in isolated pancreatic acini of the rat. Chlorobutanol (1 mg ml-1) markedly inhibited the secretory response to cholecystokinin octapeptide (CCK-8), carbamylcholine chloride (carbachol), or sodium fluoride, a direct G-protein activator. However, chlorobutanol itself induced a maximal release of amylase when the dose was increased to 4 mg ml-1. Chlorobutanol inhibited 13 pM [125I]-CCK-8 or 0.5 nM [3H]-methylscopolamine chloride binding to the acinar cells in a dose-dependent manner. These results indicate that chlorobutanol produces discernible pharmacological effects on the secretory response in rat pancreatic acinar cells through changes in the Ca2+ dynamics.
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100000092147
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SUB11812MIG
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760101
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1309399
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C45678
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CONCEPT | Industrial Aid | ||
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DTXSID9022235
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3X4P6271OX
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5284505
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6001-64-5
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CHLOROBUTANOL HEMIHYDRATE
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odour, characteristic, camphoraceous.Solubility: Slightly soluble in water; very soluble in ethanol (~750 g/l) TS and ether R; soluble in glycerol R.Category: Antimicrobial preservative.Storage: Chlorobutanol should be kept in a tightly closed container.Labelling: The designation on the container of Chlorobutanol should state whether it is the hemihydrate or the anhydrous form. | ||
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C79995
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3X4P6271OX
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ACTIVE MOIETY
SUBSTANCE RECORD
