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Details

Stereochemistry ACHIRAL
Molecular Formula 2C4H7Cl3O.H2O
Molecular Weight 372.929
Optical Activity NONE
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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Quaternary ammoniums and other preservatives' contribution in oxidative stress and apoptosis on Chang conjunctival cells.
2001 Mar
Effects of common ophthalmic preservatives on ocular health.
2001 Sep-Oct
Epithelial activity of hexokinase and glucose-6-phosphate dehydrogenase in cultured bovine lenses recovering from pharmaceutical-induced optical damage.
2003 Nov 3
Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes.
2003 Sep 19
Management of earwax in primary care--postal survey of UK GPs and practice nurses.
2004 Aug
Allergic contact dermatitis from triethanolamine polypeptide oleate condensate in eardrops and shampoo.
2005 Apr
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
Vitamin C. Biosynthesis, recycling and degradation in mammals.
2007 Jan
Conjunctival provocation test for the diagnosis of ocular hypersensitivity to chlorobutanol.
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
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
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
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
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
Efficacy and patient tolerability of travoprost BAK-free solution in patients with open-angle glaucoma and ocular hypertension.
2010 Aug 9
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
[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 Dec 15 15:47:13 UTC 2023
Edited
by admin
on Fri Dec 15 15:47:13 UTC 2023
Record UNII
3X4P6271OX
Record Status Validated (UNII)
Record Version
  • Download
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
SMS_ID
100000092147
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
EVMPD
SUB11812MIG
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
NSC
760101
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
RXCUI
1309399
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
CONCEPT Industrial Aid
EPA CompTox
DTXSID9022235
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
DAILYMED
3X4P6271OX
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
PUBCHEM
5284505
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
CAS
6001-64-5
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLOROBUTANOL HEMIHYDRATE
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
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 Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
FDA UNII
3X4P6271OX
Created by admin on Fri Dec 15 15:47:13 UTC 2023 , Edited by admin on Fri Dec 15 15:47:13 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY