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Details

Stereochemistry ACHIRAL
Molecular Formula 2C17H27Cl2N5.2ClH.H2O
Molecular Weight 835.609
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLANEXIDINE HYDROCHLORIDE

SMILES

O.Cl.Cl.CCCCCCCCNC(=N)NC(=N)NCC1=CC=C(Cl)C(Cl)=C1.CCCCCCCCNC(=N)NC(=N)NCC2=CC=C(Cl)C(Cl)=C2

InChI

InChIKey=PMKCJSVTNJUCGR-UHFFFAOYSA-N
InChI=1S/2C17H27Cl2N5.2ClH.H2O/c2*1-2-3-4-5-6-7-10-22-16(20)24-17(21)23-12-13-8-9-14(18)15(19)11-13;;;/h2*8-9,11H,2-7,10,12H2,1H3,(H5,20,21,22,23,24);2*1H;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 C17H27Cl2N5
Molecular Weight 372.336
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Olanexidine [1-(3,4-dichlorobenzyl)-5-octylbiguanide] (formerly OPB-2045), an antimicrobial agent exhibited antimicrobial activity against a wide range of bacteria, especially Gram-positive bacteria, was synthesized in 1997. To optimize its use as a topical antiseptic, olanexidine was converted to the gluconate salt. The resulting formulation (OPB) had more potent bactericidal activity against methicillin-resistant S. aureus and vancomycin-resistant enterococci in both in vitro and in vivo animal models than chlorhexidine and PVP-I. The mechanism of action was considered to be follows: olanexidine binds to the cell membrane, disrupts membrane integrity, and exerts its bacteriostatic and bactericidal activities by causing the irreversible leakage of intracellular components. At relatively high concentrations, olanexidine aggregates the cells through a protein-denaturing effect.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: bacterial cell membrane
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Olanedine

Approved Use

Unknown

Launch Date

2015
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

antiseptic
Route of Administration: Topical
In Vitro Use Guide
olanexidine interacts with the bacterial surface molecules, such as lipopolysaccharide and lipoteichoic acid, disrupts the cell membranes of liposomes, which are artificial bacterial membrane models, (iii) enhances the membrane permeability of Escherichia coli, (iv) disrupts the membrane integrity of S. aureus, and (v) denatures proteins at relatively high concentrations (>160 g/ml)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:33:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:33:38 GMT 2023
Record UNII
R296398ALN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLANEXIDINE HYDROCHLORIDE
USAN  
USAN  
Official Name English
OLANEXIDINE HYDROCHLORIDE [USAN]
Common Name English
OPB-2045
Code English
IMIDODICARBONIMIDIC DIAMIDE, N-((3,4-DICHLOROPHENYL)METHYL)-N'-OCTYL-, HYDROCHLORIDE, HYDRATE (2:2:1)
Systematic Name English
OLANEXIDINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
IMIDODICARBONIMIDIC DIAMIDE, N-((3,4-DICHLOROPHENYL)METHYL)-N'-OCTYL-, MONOHYDROCHLORIDE, HYDRATE (2:1)
Common Name English
OLANEXIDINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
1-(3,4-Dichlorobenzyl)-5-octylbiguanide monohydrochloride hemihydrate
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID80176237
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
USAN
LL-28
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
CAS
218282-71-4
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
FDA UNII
R296398ALN
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1190262
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
PUBCHEM
636390
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
NCI_THESAURUS
C170244
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
SMS_ID
300000032699
Created by admin on Fri Dec 15 15:33:38 GMT 2023 , Edited by admin on Fri Dec 15 15:33:38 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY