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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 of CHLOROBUTANOL

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

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:
healthy, 20-30
Health Status: healthy
Age Group: 20-30
Sex: M
Sources:
Other AEs: Sedation, Light headedness...
Other AEs:
Sedation
Light headedness
Euphoria
Sources:
AEs

AEs

AESignificanceDosePopulation
Euphoria
600 mg single, oral
Studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 20-30
Health Status: healthy
Age Group: 20-30
Sex: M
Sources:
Light headedness
600 mg single, oral
Studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 20-30
Health Status: healthy
Age Group: 20-30
Sex: M
Sources:
Sedation
600 mg single, oral
Studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 20-30
Health Status: healthy
Age Group: 20-30
Sex: M
Sources:
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
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
Allergic contact dermatitis from triethanolamine polypeptide oleate condensate in eardrops and shampoo.
2005 Apr
Application of a capillary electrophoresis method for simultaneous determination of preservatives in pharmaceutical formulations.
2005 Feb
[The treatment of hyperemesis gravidarum with chlorobutanol-caffeine rectal suppositories in Denmark: practice and evidence].
2007 May 28
In vitro permeation of desmopressin across rabbit nasal mucosa from liquid nasal sprays: the enhancing effect of potassium sorbate.
2009 Apr 11
Minimally invasive strabismus surgery (MISS) for inferior obliquus recession.
2009 Feb
Regeneration of the radial nerve cord in the sea cucumber Holothuria glaberrima.
2009 Jan 6
[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 Mon Mar 31 18:15:22 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:22 GMT 2025
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, ANHYDROUS
EP   II   WHO-IP  
Preferred Name English
chlorobutanol [INN]
Common Name English
CHLOROBUTANOL, ANHYDROUS [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 [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
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
WHO-ATC A04AD54
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
EPA PESTICIDE CODE 17501
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
CFR 21 CFR 310.538
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
WHO-VATC QA04AD54
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
WHO-VATC QA04AD04
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
WHO-ATC A04AD04
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
Code System Code Type Description
INN
440
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
FDA UNII
HM4YQM8WRC
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
SMS_ID
100000081866
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
CONCEPT Industrial Aid
DRUG CENTRAL
3092
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
NCI_THESAURUS
C65317
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
NSC
44794
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
EVMPD
SUB11813MIG
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
ChEMBL
CHEMBL1439973
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
HSDB
2761
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLOROBUTANOL
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
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 Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
PUBCHEM
5977
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
DRUG BANK
DB11386
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
CAS
57-15-8
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
RS_ITEM_NUM
1112503
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
MESH
D002724
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
EVMPD
SUB06190MIG
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID1041217
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
WIKIPEDIA
CHLOROBUTANOL
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
MERCK INDEX
m3399
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY Merck Index
RXCUI
2378
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY RxNorm
DAILYMED
HM4YQM8WRC
Created by admin on Mon Mar 31 18:15:22 GMT 2025 , Edited by admin on Mon Mar 31 18:15:22 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY