CHLOROBUTANOL

US Previously Marketed

First marketed in 1911

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H7Cl3O
Molecular Weight	177.457
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	177.457
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 27 Target ID: CHEMBL4187 Sources: https://www.isaponline.org/application/files/8214/7034/5599/ISAP_AM_2011_Abstracts_3.pdf	Inhibitor 8297		3.9 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.isaponline.org/application/files/8214/7034/5599/ISAP_AM_2011_Abstracts_3.pdf	Preventing		Not Provided 504	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 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
Structural elucidation of disinfection by-products in treated drinking water.	2001	11268128
Quaternary ammoniums and other preservatives' contribution in oxidative stress and apoptosis on Chang conjunctival cells.	2001 Mar	11222522
Ear drops for the removal of ear wax.	2003	12918014
Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques.	2003	12866935
Randomized clinical trial of docusate, triethanolamine polypeptide, and irrigation in cerumen removal in children.	2003 Dec	14662569
4-Chlorobutanol induces unusual reversible and irreversible thermal unfolding of ribonuclease A: thermodynamic, kinetic, and conformational characterization.	2004 Apr	15178004
Preventing exposure keratopathy in the critically ill: a prospective study comparing eye care regimes.	2005 Aug	16024871
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
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
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
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
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
Allergy to ophthalmic preservatives.	2009 Oct	19697451
[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 Dec 15 15:59:02 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:02 GMT 2023`
Record UNII	HM4YQM8WRC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLOROBUTANOL

Official Name

English

chlorobutanol [INN]

Common Name

English

CHLOROBUTANOL, ANHYDROUS [WHO-IP]

Common Name

English

CHLOROBUTANOL, ANHYDROUS

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 [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

Chlorobutanol [WHO-DD]

Common Name

English

2-PROPANOL, 1,1,1-TRICHLORO-2-METHYL-

Systematic Name

English

CHLOROBUTANOL, ANHYDROUS [EP IMPURITY]

Common Name

English

1,1,1-Trichloro-2-methyl-2-propanol

Systematic Name

English

ACETONE CHLOROFORM

Systematic Name

English

ANHYDROUS CHLOROBUTANOL

Common Name

English

CHLORETONE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

98896