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 |
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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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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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Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes. | 2003 Sep 19 |
|
Chronic tinnitus resulting from cerumen removal procedures. | 2004 |
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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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Randomized, placebo-controlled evaluation of Cerumenex and Murine earwax removal products. | 2004 Oct |
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Preventing exposure keratopathy in the critically ill: a prospective study comparing eye care regimes. | 2005 Aug |
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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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Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage. | 2007 |
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[Contact allergy to triethanolamine in ear drops and shampoo]. | 2007 Jan |
|
Vitamin C. Biosynthesis, recycling and degradation in mammals. | 2007 Jan |
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[Efficacy of an antiseptic dialysis of purulent wounds in the dentofacial region with hyvalix]. | 2007 Jul-Sep |
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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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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 |
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Common cellular events occur during wound healing and organ regeneration in the sea cucumber Holothuria glaberrima. | 2007 Oct 18 |
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Minimally invasive strabismus surgery for horizontal rectus muscle reoperations. | 2008 Dec |
|
Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla. | 2008 Mar |
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GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture. | 2009 Apr |
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Comparative toxicity of preservatives on immortalized corneal and conjunctival epithelial cells. | 2009 Apr |
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Randomized, placebo-controlled evaluation of chlorobutanol, potassium carbonate, and irrigation in cerumen removal. | 2009 Aug |
|
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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Methadone-associated Q-T interval prolongation and torsades de pointes. | 2009 May 1 |
|
Modification of cell wall properties in lettuce improves shelf life. | 2010 Feb |
|
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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[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
Wed Jul 05 23:27:18 UTC 2023
by
admin
on
Wed Jul 05 23:27:18 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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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
98896
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WHO-ATC |
A04AD54
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admin on Wed Jul 05 23:27:18 UTC 2023 , Edited by admin on Wed Jul 05 23:27:18 UTC 2023
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EPA PESTICIDE CODE |
17501
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admin on Wed Jul 05 23:27:18 UTC 2023 , Edited by admin on Wed Jul 05 23:27:18 UTC 2023
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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 Wed Jul 05 23:27:18 UTC 2023 , Edited by admin on Wed Jul 05 23:27:18 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 |