CLOFOCTOL

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H26Cl2O
Molecular Weight	365.337
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)CC(C)(C)C1=CC(CC2=CC=C(Cl)C=C2Cl)=C(O)C=C1

InChI

InChIKey=HQVZOORKDNCGCK-UHFFFAOYSA-N

InChI=1S/C21H26Cl2O/c1-20(2,3)13-21(4,5)16-7-9-19(24)15(11-16)10-14-6-8-17(22)12-18(14)23/h6-9,11-12,24H,10,13H2,1-5H3

HIDE SMILES / InChI

Molecular Formula	C21H26Cl2O
Molecular Weight	365.337
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.mims.com/india/drug/info/clofoctol?mtype=generic

Clofoctol [2-(2,4-dichlorobenzyl)-4-(tetramethyl-1,1,3,3-butyl)phenol] is a synthetic antibacterial agent with bactericidal activity on various Gram-positive (especially S. pyogenes and S. pneumoniae, but also Corynebacterium spp. and Propionibacterium acnes) and some Gram-negative bacteria (including Haemophilus influenzae, Bordetella spp., Neisseria meningitides, and Neisseria gonorrhea). A peculiar property of clofoctol is the rapidity of the antimicrobial effect, similar to that of antiseptic compounds, which makes the development of resistance less likely. Following rectal administration of clofoctol, absorption is rapid and nearly complete (about 98%), with a good penetration in the lung tissue. Clofoctol is primarily metabolized by hepatic glucuronidation and excreted through the biliary system; renal elimination is negligible. Clofoctol compound has been used mainly in France (under the trade name Octoplus ) and Italy (as Gramplus) for the treatment of mild upper respiratory tract infections, especially in pediatric patients

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Streptococcus pyogenes 6 Target ID: CHEMBL356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23040683	Inhibitor 8504
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23040683	Inhibitor 8504
Haemophilus influenzae 10 Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23040683	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Upper respiratory tract infections 12 Sources: https://www.torrinomedica.it/farmaci/schedetecniche/GRAMPLUS.asp	Curative		Approved 8583	Gramplus Approved Use Acute and chronic infections of the upper respiratory tract and their appendages. Tracheobronchial infections. Anti-infective treatment after otorhinolaryngology.

C_max

Value	Dose	Co-administered	Analyte	Population
38.07 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3610901/	1.5 g single, rectal dose: 1.5 g route of administration: Rectal experiment type: SINGLE co-administered:		CLOFOCTOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
80.91 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3610901/	1.5 g single, rectal dose: 1.5 g route of administration: Rectal experiment type: SINGLE co-administered:		CLOFOCTOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3610901/	1.5 g single, rectal dose: 1.5 g route of administration: Rectal experiment type: SINGLE co-administered:		CLOFOCTOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
750 mg 2 times / day multiple, rectal Recommended Dose: 750 mg, 2 times / day Route: rectal Route: multiple Dose: 750 mg, 2 times / day Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	Disc. AE: Coma, Respiratory depression... Other AEs: Hypotension, Hypothermia... AEs leading to discontinuation/dose reduction: Coma Respiratory depression Other AEs: Hypotension Hypothermia Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic

AEs

AE	Significance	Dose	Population
Hypotension		750 mg 2 times / day multiple, rectal Recommended Dose: 750 mg, 2 times / day Route: rectal Route: multiple Dose: 750 mg, 2 times / day Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic
Hypothermia		750 mg 2 times / day multiple, rectal Recommended Dose: 750 mg, 2 times / day Route: rectal Route: multiple Dose: 750 mg, 2 times / day Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic
Coma	Disc. AE	750 mg 2 times / day multiple, rectal Recommended Dose: 750 mg, 2 times / day Route: rectal Route: multiple Dose: 750 mg, 2 times / day Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic
Respiratory depression	Disc. AE	750 mg 2 times / day multiple, rectal Recommended Dose: 750 mg, 2 times / day Route: rectal Route: multiple Dose: 750 mg, 2 times / day Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/philippines/drug/info/clofoctol?mtype=generic

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150 inducer 1087	inhibitor 2438	inhibitor 2507	substrate 9

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OATP1B1 1079 CYP2C19 2057 CYP1A2 2153 CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 19.0	inconclusive [IC50 17.3768 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 212.0	no
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTQ3NjYwNSJ9fQ==	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 222.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 2.0	yes [IC50 1.7377 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 16.0	yes [IC50 15.4871 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 4.0	yes [IC50 3.0901 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 5.0	yes [IC50 6.1655 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE0NzY2MDUifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE0NzY2MDUifX0=	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 28 \| 222	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	substrate 9 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2799#section=BioAssay-Results Page: 35.0

PubMed

Title	Date	PubMed
Identification by automated screening of a small molecule that selectively eliminates neural stem cells derived from hESCs but not dopamine neurons.	2009-09-23	19774075

Patents

Sample Use Guides

In Vivo Use Guide

750 mg bid.

Route of Administration: Other

In Vitro Use Guide

In vitro experiments were performed with 226 bacterial strains clinically isolated between 2005 and 2009. The strains and numbers used were: penicillin-susceptible S. pneumoniae (n553), penicillin-resistant S. pneumoniae, S. pyogenes, methicillin-susceptible S. aureus., methicillin-resistant S. aureus., and H. influenzae. Mueller–Hinton (MH) agar plates broth media containing serial twofold dilutions of clofoctol, amoxicillin, or erythromycin at concentrations ranging from 0.125 to 32 mg/ml were prepared and placed in a 96-well microplate. A bacterial suspension of approximately 56105 CFU/ml was inoculated into each well and the MICs were recorded after 24 hours of incubation at 37C in ambient air.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:57:07 GMT 2025` Edited by `admin` on `Wed Apr 02 09:57:07 GMT 2025`
Record UNII	704083NI0R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOFOCTOL

Official Name

English

OCTOFENE

Preferred Name

English

Clofoctol [WHO-DD]

Common Name

English

clofoctol [INN]

Common Name

English

CLOFOCTOL [MI]

Common Name

English

CLOFOCTOL [MART.]

Common Name

English

.ALPHA.-(2,4-DICHLOROPHENYL)-4-(1,1,3,3-TETRAMETHYLBUTYL)-O-CRESOL

Common Name

English

NSC-758389

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C52588