Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H7Cl3O |
Molecular Weight | 177.457 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(O)C(Cl)(Cl)Cl
InChI
InChIKey=OSASVXMJTNOKOY-UHFFFAOYSA-N
InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3
Molecular Formula | C4H7Cl3O |
Molecular Weight | 177.457 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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Is ketamine or its preservative responsible for neurotoxicity in the rabbit? | 1993 Jan |
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Effects of common ophthalmic preservatives on ocular health. | 2001 Sep-Oct |
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Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. | 2003 |
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Review of a randomized trial comparing 2 cerumenolytic agents. | 2003 Dec |
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Randomized clinical trial of docusate, triethanolamine polypeptide, and irrigation in cerumen removal in children. | 2003 Dec |
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Epithelial activity of hexokinase and glucose-6-phosphate dehydrogenase in cultured bovine lenses recovering from pharmaceutical-induced optical damage. | 2003 Nov 3 |
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Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose. | 2003 Oct 31 |
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Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes. | 2003 Sep 19 |
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Chronic tinnitus resulting from cerumen removal procedures. | 2004 |
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4-Chlorobutanol induces unusual reversible and irreversible thermal unfolding of ribonuclease A: thermodynamic, kinetic, and conformational characterization. | 2004 Apr |
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Management of earwax in primary care--postal survey of UK GPs and practice nurses. | 2004 Aug |
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A randomised controlled study of the efficacy of hypromellose and Lacri-Lube combination versus polyethylene/Cling wrap to prevent corneal epithelial breakdown in the semiconscious intensive care patient. | 2004 Jun |
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Neurotoxicity of intra-arterial papaverine preserved with chlorobutanol used for the treatment of cerebral vasospasm after aneurysmal subarachnoid hemorrhage. | 2004 Nov |
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Randomized, placebo-controlled evaluation of Cerumenex and Murine earwax removal products. | 2004 Oct |
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Allergic contact dermatitis from triethanolamine polypeptide oleate condensate in eardrops and shampoo. | 2005 Apr |
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Preventing exposure keratopathy in the critically ill: a prospective study comparing eye care regimes. | 2005 Aug |
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Application of a capillary electrophoresis method for simultaneous determination of preservatives in pharmaceutical formulations. | 2005 Feb |
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Assessment of corneal epitheliopathy in the critically ill. | 2005 Feb |
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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 |
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Cerumen removal products. | 2005 Sep-Oct |
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Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver. | 2006 Apr |
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Are multidose over-the-counter artificial tears adequately preserved? | 2006 May |
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Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
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[Contact allergy to triethanolamine in ear drops and shampoo]. | 2007 Jan |
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Vitamin C. Biosynthesis, recycling and degradation in mammals. | 2007 Jan |
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Conjunctival provocation test for the diagnosis of ocular hypersensitivity to chlorobutanol. | 2007 Jan |
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Effect of ophthalmic solution components on acrylic intraocular lenses. | 2007 Jan |
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Development and validation of a stability-indicating analytical method for the quantitation of oxytocin in pharmaceutical dosage forms. | 2007 Jan 4 |
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[The treatment of hyperemesis gravidarum with chlorobutanol-caffeine rectal suppositories in Denmark: practice and evidence]. | 2007 May 28 |
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Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells. | 2008 Aug |
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Development and evaluation of a chloramphenicol hypertonic ophthalmic solution. | 2008 Jan |
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Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla. | 2008 Mar |
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DNA damage in preserved specimens and tissue samples: a molecular assessment. | 2008 Oct 23 |
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Ocular preservatives: associated risks and newer options. | 2009 |
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GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture. | 2009 Apr |
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Randomized, placebo-controlled evaluation of chlorobutanol, potassium carbonate, and irrigation in cerumen removal. | 2009 Aug |
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Evidence that phosphatidylinositol 3-kinase is involved in sperm-induced tyrosine kinase signaling in Xenopus egg fertilization. | 2009 Dec 17 |
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Minimally invasive strabismus surgery (MISS) for inferior obliquus recession. | 2009 Feb |
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Regeneration of the radial nerve cord in the sea cucumber Holothuria glaberrima. | 2009 Jan 6 |
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Methadone-associated Q-T interval prolongation and torsades de pointes. | 2009 May 1 |
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Therapeutic approaches to cerebral vasospasm complicating ruptured aneurysm. | 2009 Nov 16 |
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Allergy to ophthalmic preservatives. | 2009 Oct |
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Interactions at human ether-à-go-go-related gene channels. | 2010 Apr |
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Efficacy and patient tolerability of travoprost BAK-free solution in patients with open-angle glaucoma and ocular hypertension. | 2010 Aug 9 |
|
Modification of cell wall properties in lettuce improves shelf life. | 2010 Feb |
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Evaluation of acute corneal barrier change induced by topically applied preservatives using corneal transepithelial electric resistance in vivo. | 2010 Jan |
|
The world's richest tadpole communities show functional redundancy and low functional diversity: ecological data on Madagascar's stream-dwelling amphibian larvae. | 2010 May 12 |
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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 |
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[Chlorobutanol poisoning: about a case]. | 2010 Oct |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7689400
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:59:02 UTC 2023
by
admin
on
Fri Dec 15 15:59:02 UTC 2023
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Record UNII |
HM4YQM8WRC
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
98896
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WHO-ATC |
A04AD54
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EPA PESTICIDE CODE |
17501
Created by
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CFR |
21 CFR 310.538
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WHO-VATC |
QA04AD54
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WHO-VATC |
QA04AD04
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WHO-ATC |
A04AD04
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440
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HM4YQM8WRC
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100000081866
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C45678
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CONCEPT | Industrial Aid | ||
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3092
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C65317
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44794
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SUB11813MIG
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CHEMBL1439973
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2761
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CHLOROBUTANOL
Created by
admin on Fri Dec 15 15:59:02 UTC 2023 , Edited by admin on Fri Dec 15 15:59:02 UTC 2023
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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. | ||
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200-317-6
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5977
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DB11386
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57-15-8
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1112503
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D002724
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SUB06190MIG
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DTXSID1041217
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CHLOROBUTANOL
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m3399
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PRIMARY | Merck Index | ||
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2378
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PRIMARY | RxNorm | ||
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HM4YQM8WRC
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |