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Details

Stereochemistry ACHIRAL
Molecular Formula 2C4H7Cl3O.H2O
Molecular Weight 372.9288
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROBUTANOL HEMIHYDRATE

SMILES

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

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
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
Effects of common ophthalmic preservatives on ocular health.
2001 Sep-Oct
Clinical inquiries. What is the best treatment for impacted cerumen?
2002 Feb
Ear drops for the removal of ear wax.
2003
Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques.
2003
Review of a randomized trial comparing 2 cerumenolytic agents.
2003 Dec
QTc interval prolongation associated with intravenous methadone.
2003 Oct
Convenient preparation of L-arabino-hexos-5-ulose derivatives from lactose.
2003 Oct 31
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
Neurotoxicity of intra-arterial papaverine preserved with chlorobutanol used for the treatment of cerebral vasospasm after aneurysmal subarachnoid hemorrhage.
2004 Nov
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Vitamin C. Biosynthesis, recycling and degradation in mammals.
2007 Jan
GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture.
2009 Apr
In vitro permeation of desmopressin across rabbit nasal mucosa from liquid nasal sprays: the enhancing effect of potassium sorbate.
2009 Apr 11
Randomized, placebo-controlled evaluation of chlorobutanol, potassium carbonate, and irrigation in cerumen removal.
2009 Aug
Regeneration of the radial nerve cord in the sea cucumber Holothuria glaberrima.
2009 Jan 6
Allergy to ophthalmic preservatives.
2009 Oct
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.
Name Type Language
CHLOROBUTANOL HEMIHYDRATE
EP   II   WHO-DD   WHO-IP  
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 [EP MONOGRAPH]
Common Name English
CHLOROBUTANOL HEMIHYDRATE [II]
Common Name English
NSC-760101
Code 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 Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY
RXCUI
1309399
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C45678
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
CONCEPT Industrial Aid
EPA CompTox
6001-64-5
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY
PUBCHEM
5284505
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY
CAS
6001-64-5
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLOROBUTANOL HEMIHYDRATE
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 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.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 Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY
FDA UNII
3X4P6271OX
Created by admin on Fri Jun 25 21:11:08 UTC 2021 , Edited by admin on Fri Jun 25 21:11:08 UTC 2021
PRIMARY