U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula 2C4H7Cl3O.H2O
Molecular Weight 372.929
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROBUTANOL HEMIHYDRATE

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

HIDE SMILES / InChI

Description

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.9 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PubMed

PubMed

TitleDatePubMed
Is ketamine or its preservative responsible for neurotoxicity in the rabbit?
1993 Jan
Chronic tinnitus resulting from cerumen removal procedures.
2004
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
Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver.
2006 Apr
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
Vitamin C. Biosynthesis, recycling and degradation in mammals.
2007 Jan
Conjunctival provocation test for the diagnosis of ocular hypersensitivity to chlorobutanol.
2007 Jan
Effect of ophthalmic solution components on acrylic intraocular lenses.
2007 Jan
Development and validation of a stability-indicating analytical method for the quantitation of oxytocin in pharmaceutical dosage forms.
2007 Jan 4
[Efficacy of an antiseptic dialysis of purulent wounds in the dentofacial region with hyvalix].
2007 Jul-Sep
[The treatment of hyperemesis gravidarum with chlorobutanol-caffeine rectal suppositories in Denmark: practice and evidence].
2007 May 28
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
Common cellular events occur during wound healing and organ regeneration in the sea cucumber Holothuria glaberrima.
2007 Oct 18
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells.
2008 Aug
Minimally invasive strabismus surgery for horizontal rectus muscle reoperations.
2008 Dec
Development and evaluation of a chloramphenicol hypertonic ophthalmic solution.
2008 Jan
Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla.
2008 Mar
DNA damage in preserved specimens and tissue samples: a molecular assessment.
2008 Oct 23
Ocular preservatives: associated risks and newer options.
2009
GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture.
2009 Apr
Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - a potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals.
2009 Apr
Comparative toxicity of preservatives on immortalized corneal and conjunctival epithelial cells.
2009 Apr
In vitro permeation of desmopressin across rabbit nasal mucosa from liquid nasal sprays: the enhancing effect of potassium sorbate.
2009 Apr 11
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
Evidence that phosphatidylinositol 3-kinase is involved in sperm-induced tyrosine kinase signaling in Xenopus egg fertilization.
2009 Dec 17
Minimally invasive strabismus surgery (MISS) for inferior obliquus recession.
2009 Feb
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
Methadone-associated Q-T interval prolongation and torsades de pointes.
2009 May 1
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
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
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
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
Patents

Sample Use Guides

In Vitro Use Guide
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.
Name Type Language
CHLOROBUTANOL HEMIHYDRATE
EP   II   WHO-DD   WHO-IP  
Common Name English
CHLOROBUTANOL HEMIHYDRATE [EP]
Common Name English
2-PROPANOL, 1,1,1-TRICHLORO-2-METHYL-, HEMIHYDRATE
Common Name English
1,1,1-TRICHLORO-2-METHYL-2-PROPANOL HEMIHYDRATE
Common Name English
CHLOROBUTANOL HEMIHYDRATE [II]
Common Name English
CHLOROBUTANOL HEMIHYDRATE [WHO-DD]
Common Name English
CHLOROBUTANOL HEMIHYDRATE [WHO-IP]
Common Name English
Code System Code Type Description
EVMPD
SUB11812MIG
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY
RXCUI
1309399
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C45678
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
CONCEPT Industrial Aid
EPA CompTox
6001-64-5
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY
PUBCHEM
5284505
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY
CAS
6001-64-5
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLOROBUTANOL HEMIHYDRATE
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
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.
NCI_THESAURUS
C79995
Created by admin on Tue Oct 22 00:37:10 UTC 2019 , Edited by admin on Tue Oct 22 00:37:10 UTC 2019
PRIMARY