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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Is ketamine or its preservative responsible for neurotoxicity in the rabbit? | 1993 Jan |
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The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations. | 2000 Feb |
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Clinical inquiries. What is the best treatment for impacted cerumen? | 2002 Feb |
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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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Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver. | 2006 Apr |
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Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage. | 2007 |
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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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Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla. | 2008 Mar |
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Comparative toxicity of preservatives on immortalized corneal and conjunctival epithelial cells. | 2009 Apr |
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A Freshwater clam (Corbicula fluminea) extract reduces cholesterol level and hepatic lipids in normal rats and xenobiotics-induced hypercholesterolemic rats. | 2009 Apr 22 |
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Therapeutic approaches to cerebral vasospasm complicating ruptured aneurysm. | 2009 Nov 16 |
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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 |
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Modification of cell wall properties in lettuce improves shelf life. | 2010 Feb |
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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
Fri Dec 15 15:59:02 GMT 2023
by
admin
on
Fri Dec 15 15:59:02 GMT 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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EPA PESTICIDE CODE |
17501
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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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PRIMARY | |||
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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
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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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PRIMARY | |||
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SUB06190MIG
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PRIMARY | |||
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DTXSID1041217
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PRIMARY | |||
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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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PRIMARY |
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 |