CHLOROBUTANOL HEMIHYDRATE

US Previously Marketed

First marketed in 1911

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 Search

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

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

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

Description
Sources: http://www.athenstaedt.de/download/Product_Information_Chlorobutanol.pdf

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

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type II alpha subunit 26 Target ID: CHEMBL4187 Sources: https://www.isaponline.org/application/files/8214/7034/5599/ISAP_AM_2011_Abstracts_3.pdf	Inhibitor 7728		3.9 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: https://www.isaponline.org/application/files/8214/7034/5599/ISAP_AM_2011_Abstracts_3.pdf	Preventing		Not Provided 492	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376	healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376	Other AEs: Sedation, Light headedness... Other AEs: Sedation Light headedness Euphoria Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376

AEs

AE	Dose	Population
Euphoria	600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376	healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376
Light headedness	600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376	healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376
Sedation	600 mg single, oral Studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376	healthy, 20-30 n = 4 Health Status: healthy Age Group: 20-30 Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/7159691 Page: p.376

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://www.ema.europa.eu/en/documents/scientific-guideline/chmp-safety-working-partys-response-cmdh-questions-chlorobutanol_en.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY561036	https://www.001chemical.com/chem/57-15-8
3B Scientific (Wuhan) Corp	3B3-033157	http://www.3bsc.com/index/pro_info.php?id=54421
AHH Chemical co.,ltd	MT-26160	http://www.ahhchemical.com/product/MT-26160.html
Accela ChemBio Inc	SY277495	http://www.accelachem.com/cn/search.html?keyword=SY277495&attname=GoodsCode
Achemtek	0104-014893	http://www.achemtek.com/57-15-8
Acorn PharmaTech	ACN-037780	http://www.acornpharmatech.com/
Alfa Chemistry	28471-22-9	https://www.alfa-chemistry.com/cas_28471-22-9.htm
Allbio Pharm Co., Ltd	AD03646	http://www.allbiopharm.com/product/n/AD03646
Ambeed	A829380	https://www.ambeed.com/products/57-15-8.html
Ark Pharm	AK00061249	http://www.arkpharminc.com/products/57-15-8.html
Aurora Fine Chemicals LLC	K02.100.495	http://online.aurorafinechemicals.com/info?ID=K02.100.495
Aurum Pharmatech LLC	NE21463	http://www.Aurumpharmatech.com/Product/ProductDetails/NE21463
BLD Pharm	BD52008	http://www.bldpharm.com/products/57-15-8.html
BioSynth	W-105484	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-105484.html
CSNpharm	CSN21964	https://www.csnpharm.com/products/chlorobutanol.html
Chem Scene	CS-B1703	http://www.chemscene.com/57-15-8.html
ChemMol	49416380	http://www.chemmol.com/chemmol/49416380.html
ChemMol	99057858	http://www.chemmol.com/chemmol/99057858.html
Chemspace	CSSB00000210252	https://chem-space.com/CSSB00000210252
Clearsynth	CS-EB-00475	https://www.clearsynth.com/en/CSEB00475.html
Enamine	Z1259084902	https://www.enaminestore.com/catalog/Z1259084902
Finetech	FT-0612881	http://www.finetechnology-ind.com/prod/detail/pub/57-15-8.html
Finetech	FT-0605936	http://www.finetechnology-ind.com/prod/detail/pub/6001-64-5.html
Lab Network	LN00226967	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00226967
MedChem Express	HY-B1263	https://www.medchemexpress.com/chlorobutanol.html
Molcore	MC561036	https://www.molcore.com/product/57-15-8
OlainFarm JSC	Chlorobutanol Hemihydrate	http://www.olainfarm.lv/product/chlorobutanol-hemihydrate/
Otava	2848491	https://search.otavachemicals.com/#!/search?query=2848491&type=code&base=dbb
Selleck Chemicals	S3705	http://www.selleckchem.com/products/chlorobutanol.html
Smolecule	S523513	http://www.smolecule.com/products/s523513
Smolecule	S772652	https://www.smolecule.com/products/s772652
TCI (Tokyo Chemical Industry)	T0386	http://www.tcichemicals.com/eshop/en/us/commodity/T0386/index.html
THE BioTek	bt-264172	https://www.thebiotek.com/product/inhibitors/bt-264172
abcr GmbH	AB539259	http://www.abcr.com/shop/en/AB539259
iChemical	EBD2761144	http://www.ichemical.com/products/57-15-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7565024869	https://mcule.com/MCULE-7565024869/

PubMed

Title	Date	PubMed
Is ketamine or its preservative responsible for neurotoxicity in the rabbit?	1993 Jan	8424543
Chronic tinnitus resulting from cerumen removal procedures.	2004	15379348
Management of earwax in primary care--postal survey of UK GPs and practice nurses.	2004 Aug	15249529
Neurotoxicity of intra-arterial papaverine preserved with chlorobutanol used for the treatment of cerebral vasospasm after aneurysmal subarachnoid hemorrhage.	2004 Nov	15472097
Randomized, placebo-controlled evaluation of Cerumenex and Murine earwax removal products.	2004 Oct	15492164
Allergic contact dermatitis from triethanolamine polypeptide oleate condensate in eardrops and shampoo.	2005 Apr	15860001
Preventing exposure keratopathy in the critically ill: a prospective study comparing eye care regimes.	2005 Aug	16024871
Application of a capillary electrophoresis method for simultaneous determination of preservatives in pharmaceutical formulations.	2005 Feb	15754820
Assessment of corneal epitheliopathy in the critically ill.	2005 Feb	15565358
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	16209608
Cerumen removal products.	2005 Sep-Oct	16202844
Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver.	2006 Apr	16689937
Are multidose over-the-counter artificial tears adequately preserved?	2006 May	16670481
Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage.	2007	17705883
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
[Contact allergy to triethanolamine in ear drops and shampoo].	2007 Jan	17384563
Vitamin C. Biosynthesis, recycling and degradation in mammals.	2007 Jan	17222174
Conjunctival provocation test for the diagnosis of ocular hypersensitivity to chlorobutanol.	2007 Jan	17198021
Effect of ophthalmic solution components on acrylic intraocular lenses.	2007 Jan	17189806
Development and validation of a stability-indicating analytical method for the quantitation of oxytocin in pharmaceutical dosage forms.	2007 Jan 4	16920323
[Efficacy of an antiseptic dialysis of purulent wounds in the dentofacial region with hyvalix].	2007 Jul-Sep	18416174
[The treatment of hyperemesis gravidarum with chlorobutanol-caffeine rectal suppositories in Denmark: practice and evidence].	2007 May 28	17553397
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	17786546
Common cellular events occur during wound healing and organ regeneration in the sea cucumber Holothuria glaberrima.	2007 Oct 18	17945004
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells.	2008 Aug	18954319
Minimally invasive strabismus surgery for horizontal rectus muscle reoperations.	2008 Dec	18782805
Development and evaluation of a chloramphenicol hypertonic ophthalmic solution.	2008 Jan	20390083
Ototoxicity of triethanolamine polypeptide (cerumenex) in the chinchilla.	2008 Mar	18090863
DNA damage in preserved specimens and tissue samples: a molecular assessment.	2008 Oct 23	18947416
Ocular preservatives: associated risks and newer options.	2009	19505226
GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture.	2009 Apr	19406012
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	19298702
Comparative toxicity of preservatives on immortalized corneal and conjunctival epithelial cells.	2009 Apr	19284328
In vitro permeation of desmopressin across rabbit nasal mucosa from liquid nasal sprays: the enhancing effect of potassium sorbate.	2009 Apr 11	19162181
A Freshwater clam (Corbicula fluminea) extract reduces cholesterol level and hepatic lipids in normal rats and xenobiotics-induced hypercholesterolemic rats.	2009 Apr 22	19275237
Randomized, placebo-controlled evaluation of chlorobutanol, potassium carbonate, and irrigation in cerumen removal.	2009 Aug	19746751
Evidence that phosphatidylinositol 3-kinase is involved in sperm-induced tyrosine kinase signaling in Xenopus egg fertilization.	2009 Dec 17	20015408
Minimally invasive strabismus surgery (MISS) for inferior obliquus recession.	2009 Feb	18958486
Atlantic salmon eggs favour sperm in competition that have similar major histocompatibility alleles.	2009 Feb 7	18854296
Regeneration of the radial nerve cord in the sea cucumber Holothuria glaberrima.	2009 Jan 6	19126208
Methadone-associated Q-T interval prolongation and torsades de pointes.	2009 May 1	19386945
Therapeutic approaches to cerebral vasospasm complicating ruptured aneurysm.	2009 Nov 16	21577350
Interactions at human ether-à-go-go-related gene channels.	2010 Apr	20071423
Efficacy and patient tolerability of travoprost BAK-free solution in patients with open-angle glaucoma and ocular hypertension.	2010 Aug 9	20714366
Modification of cell wall properties in lettuce improves shelf life.	2010 Feb	20179011
Evaluation of acute corneal barrier change induced by topically applied preservatives using corneal transepithelial electric resistance in vivo.	2010 Jan	19770721
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	20459864
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	20507624
[Chlorobutanol poisoning: about a case].	2010 Oct	20724106
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.	2010 Sep 20	20922036

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 21:11:08 UTC 2021` Edited by `admin` on `Fri Jun 25 21:11:08 UTC 2021`
Record UNII	3X4P6271OX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLOROBUTANOL HEMIHYDRATE

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