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Details

Stereochemistry ACHIRAL
Molecular Formula C20H31NO3.C6H8O7
Molecular Weight 525.5896
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTOXYVERINE CITRATE

SMILES

CCN(CC)CCOCCOC(=O)C1(CCCC1)c2ccccc2.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=AKJDEXBCRLOVTH-UHFFFAOYSA-N
InChI=1S/C20H31NO3.C6H8O7/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H31NO3
Molecular Weight 333.4658
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created using several sources including: http://www.ncbi.nlm.nih.gov/pubmed/3768695 | http://www.ncbi.nlm.nih.gov/pubmed/8057277 | https://www.drugs.com/cdi/solotuss-suspension.html | http://www.drugsupdate.com/generic/view/1197/Pentoxyverine

Pentoxyverine is a non-opioid antitussive used to prevent cough caused by common cold. It is used as an active ingredient of several oral over-the-counter cough suppressants alone or in combination with other medications, especially decongestants. Certuss is a combination of pentoxyverine and guaifenesin. Pentoxyverine is FDA pregnancy category C drug. Known as anticonvulsant, and spasmolytic agent.

CNS Activity

Curator's Comment:: Carbetapentane bindinding with high affinity to the in the brain of rats potentiated the effects of the prototypic antiepileptic drug diphenylhydantoin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
75.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
30 mg 3 times / day multiple, oral (mother), breasteeding (infant)
Overdose
Dose: 30 mg, 3 times / day
Route: oral (mother), breasteeding (infant)
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
healthy, infant
n = 1
Health Status: healthy
Age Group: infant
Population Size: 1
Sources:
Disc. AE: Respiratory failure...
AEs leading to
discontinuation/dose reduction:
Respiratory failure (acute, 1 patient)
Sources:
100 mg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: productive cough
Sources:
AEs

AEs

AESignificanceDosePopulation
Respiratory failure acute, 1 patient
Disc. AE
30 mg 3 times / day multiple, oral (mother), breasteeding (infant)
Overdose
Dose: 30 mg, 3 times / day
Route: oral (mother), breasteeding (infant)
Route: multiple
Dose: 30 mg, 3 times / day
Sources:
healthy, infant
n = 1
Health Status: healthy
Age Group: infant
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.
2000 May
A non-potentiometric sensing method for the determination of pentoxyverine with PQC sensors based on ion-pair complexes.
2001 Dec
Capacitive sensors using electropolymerized o-phenylenediamine film doped with ion-pair complex as selective elements for the determination of pentoxyverine.
2004 Jun 17
Study on the enhancement of Ru(bpy)3(2+) electrochemiluminescence by nanogold and its application for pentoxyverine detection.
2005 Dec
Anti-proliferative activity of haloperidol in B16 mouse and human SK-MEL-28 melanoma cell lines.
2005 Oct
Cold, cough, allergy, bronchodilator, and antiasthmatic drug products for over-the-counter human use; final rule for over-the-counter antitussive drug products; technical amendment. Final rule, technical amendment.
2007 Nov 30
Effects of common antitussive drugs on the hERG potassium channel current.
2008 Dec
[Quantification of pentoxyverine citrate in human plasma by LC-ESI/MS method and its application].
2009 Dec
Patents

Sample Use Guides

Pentoxyverine citrate or hydrochloride salts for adults up to 180 mg/day can be prescribed in divided doses. Pentoxyverine should be taken with food
Route of Administration: Oral
In Vitro Use Guide
1-5 mg/kg inhibited citric-acid-induced cough in guinea-pigs
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:08:45 UTC 2021
Edited
by admin
on Fri Jun 25 21:08:45 UTC 2021
Record UNII
4SH0MFJ5HJ
Record Status Validated (UNII)
Record Version
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Name Type Language
PENTOXYVERINE CITRATE
JAN   MART.   WHO-DD  
Common Name English
LOUCARBATE
Brand Name English
PENTOXYVERINE CITRATE [JAN]
Common Name English
TOCLASE
Brand Name English
PENTOXYVERINE CITRATE [MART.]
Common Name English
CARBETAPENTANE CITRATE
MI   VANDF  
Common Name English
CYCLOPENTANECARBOXYLIC ACID, 1-PHENYL-, 2-(2-(DIETHYLAMINO)ETHOXY)ETHYL ESTER, CITRATE (1:1)
Common Name English
ETHANOL, 2-(2-(DIETHYLAMINO)ETHOXY)-, 1-PHENYLCYCLOPENTANECARBOXYLATE (ESTER) CITRATE
Common Name English
PENTOXYVERINE HYDROGEN CITRATE [EP MONOGRAPH]
Common Name English
CARBETAPENTANE CITRATE [MI]
Common Name English
PENTOXYVERINE CITRATE [WHO-DD]
Common Name English
2-(2-(DIETHYLAMINO)ETHOXY)ETHYL 1-PHENYLCYCLOPENTANECARBOXYLATE CITRATE (1:1)
Systematic Name English
PENTOXYVERINE HYDROGEN CITRATE
Common Name English
NSC-757833
Code English
CARBETAPENTANE CITRATE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66917
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
Code System Code Type Description
RXCUI
283547
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
245-449-5
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
CAS
23142-01-0
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
DRUG BANK
DBSALT001543
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL73234
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
EVMPD
SUB03695MIG
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
FDA UNII
4SH0MFJ5HJ
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
NCI_THESAURUS
C76472
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
MERCK INDEX
M3065
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY Merck Index
MESH
C018861
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
EPA CompTox
23142-01-0
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
PUBCHEM
90010
Created by admin on Fri Jun 25 21:08:45 UTC 2021 , Edited by admin on Fri Jun 25 21:08:45 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY