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

Details

Stereochemistry ACHIRAL
Molecular Formula C4H7Cl3O
Molecular Weight 177.4567
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROBUTANOL

SMILES

CC(C)(C(Cl)(Cl)Cl)O

InChI

InChIKey=OSASVXMJTNOKOY-UHFFFAOYSA-N
InChI=1S/C4H7Cl3O/c1-3(2,8)4(5,6)7/h8H,1-2H3

HIDE SMILES / InChI

Molecular Formula C4H7Cl3O
Molecular Weight 177.4567
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

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 day
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

Funbound

ValueDoseCo-administeredAnalytePopulation
43%
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

Doses

DosePopulationAdverse 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
Light headedness
Euphoria
Sources: Page: p.376
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Is ketamine or its preservative responsible for neurotoxicity in the rabbit?
1993 Jan
Chronic tinnitus resulting from cerumen removal procedures.
2004
Management of earwax in primary care--postal survey of UK GPs and practice nurses.
2004 Aug
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
[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 Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:07:17 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:17 UTC 2021
Record UNII
HM4YQM8WRC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLOROBUTANOL
GREEN BOOK   HSDB   II   INCI   INN   MI   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
CHLOROBUTANOL [INN]
Common Name English
CHLOROBUTANOL, ANHYDROUS [WHO-IP]
Common Name English
CHLOROBUTANOL, ANHYDROUS
EP   II   WHO-IP  
Common Name English
CHLOROBUTANOL [EP MONOGRAPH]
Common Name English
CHLOROBUTANOL [GREEN BOOK]
Common Name English
CHLOROBUTANOL [MI]
Common Name English
CHLOROBUTANOL [JAN]
Common Name English
NSC-44794
Code English
TRICHLOROBUTANOL
Systematic Name English
CHLOROBUTANOL [WHO-IP]
Common Name English
CHLOROBUTANOL [HSDB]
Common Name English
CHLOROBUTANOL [INCI]
Common Name English
CHLOROBUTANOL, ANHYDROUS [EP]
Common Name English
CHLOROBUTANOL [II]
Common Name English
CHLOROBUTANOL [USP-RS]
Common Name English
CHLOROBUTANOLUM [WHO-IP LATIN]
Common Name English
CHLOROBUTANOL, ANHYDROUS [II]
Common Name English
CHLOROBUTANOL [VANDF]
Common Name English
2-PROPANOL, 1,1,1-TRICHLORO-2-METHYL-
Systematic Name English
1,1,1-TRICHLORO-2-METHYL-2-PROPANOL
Systematic Name English
ACETONE CHLOROFORM
Systematic Name English
CHLOROBUTANOL [WHO-DD]
Common Name English
ANHYDROUS CHLOROBUTANOL
Common Name English
CHLORETONE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 98896
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
WHO-ATC A04AD54
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
EPA PESTICIDE CODE 17501
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
CFR 21 CFR 310.538
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
WHO-VATC QA04AD54
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
WHO-VATC QA04AD04
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
WHO-ATC A04AD04
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
Code System Code Type Description
INN
440
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
FDA UNII
HM4YQM8WRC
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
CONCEPT Industrial Aid
DRUG CENTRAL
3092
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
NCI_THESAURUS
C65317
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
EVMPD
SUB11813MIG
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL1439973
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
HSDB
2761
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLOROBUTANOL
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
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.
ECHA (EC/EINECS)
200-317-6
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
PUBCHEM
5977
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
DRUG BANK
DB11386
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
CAS
57-15-8
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
MESH
D002724
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
USP_CATALOG
1112503
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY USP-RS
EVMPD
SUB06190MIG
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
EPA CompTox
57-15-8
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
WIKIPEDIA
CHLOROBUTANOL
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY
MERCK INDEX
M3399
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY Merck Index
RXCUI
2378
Created by admin on Fri Jun 25 21:07:18 UTC 2021 , Edited by admin on Fri Jun 25 21:07:18 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY