PENTOXYVERINE CITRATE

First approved in 1955

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H31NO3.C6H8O7
Molecular Weight	525.5886
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CC)CCOCCOC(=O)C1(CCCC1)C2=CC=CC=C2

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

Description
Sources: http://www.rxwiki.com/pentoxyverine
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sigma-1 receptor 6 Target ID: CHEMBL4153 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14691051	Agonist 2678		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: http://www.drugsupdate.com/generic/view/1197/Pentoxyverine	Preventing		Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/3371222	healthy, infant n = 1 Health Status: healthy Age Group: infant Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3371222	Disc. AE: Respiratory failure... AEs leading to discontinuation/dose reduction: Respiratory failure (acute, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3371222
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: https://pubmed.ncbi.nlm.nih.gov/32164969	unhealthy Health Status: unhealthy Condition: productive cough Sources: https://pubmed.ncbi.nlm.nih.gov/32164969	Sources: https://pubmed.ncbi.nlm.nih.gov/32164969

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/3371222	healthy, infant n = 1 Health Status: healthy Age Group: infant Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3371222

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://pubmed.ncbi.nlm.nih.gov/19034038/ Page: 1.0

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0170	http://www.3bsc.com/index/pro_info.php?id=19526
AA Blocks	AA008NGW	https://www.aablocks.com/goods/Goods/detail?id=AA008NGW
AHH Chemical co.,ltd	API-1156	http://www.ahhchemical.com/product/API-1156.html
AK Scientific, Inc. (AKSCI)	K344	http://www.aksci.com/item_detail.php?cat=K344
Achemtek	0104-021321	http://www.achemtek.com/77-23-6
Alichem	19117081	http://www.alichem.com/en/products/77-23-6.html
Ambinter	Amb15692761	http://www.ambinter.com/reference/15692761
BLD Pharm	BD119984	http://www.bldpharm.com/products/77-23-6.html
BioSynth	W-104325	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/W-104325.html
ChemMol	49401505	http://www.chemmol.com/chemmol/49401505.html
ChemMol	49425998	http://www.chemmol.com/chemmol/49425998.html
Chemspace	CSSB00020617750	https://chem-space.com/CSSB00020617750
Debye Scientific	DB-056191	http://www.debyesci.com/cas_77-23-6.html
Finetech	FT-0603066	http://www.finetechnology-ind.com/prod/detail/pub/77-23-6.html
Hairui	HR129976	http://www.hairuichem.com/en/product/77-23-6.html
Lab Network	LN00200057	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00200057
MolPort	MolPort-006-110-223	https://www.molport.com/shop/molecule-link/MolPort-006-110-223
Parchem	28451	http://www.parchem.com/chemical-supplier-distributor/Carbetapentane-018451.aspx
Selleck Chemicals	S0869	https://www.selleckchem.com/products/carbetapentane.html
Smolecule	S591881	https://www.smolecule.com/products/s591881
THE BioTek	bt-315140	https://www.thebiotek.com/product/others/bt-315140
eNovation Chemicals	Y1079688	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1079688
iChemical	EBD21767	http://www.ichemical.com/chemicals/cas-77-23-6

PubMed

Title	Date	PubMed
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.	2000 May	10888308
A non-potentiometric sensing method for the determination of pentoxyverine with PQC sensors based on ion-pair complexes.	2001 Dec	11783787
Capacitive sensors using electropolymerized o-phenylenediamine film doped with ion-pair complex as selective elements for the determination of pentoxyverine.	2004 Jun 17	18969481
Study on the enhancement of Ru(bpy)3(2+) electrochemiluminescence by nanogold and its application for pentoxyverine detection.	2005 Dec	16315173
Anti-proliferative activity of haloperidol in B16 mouse and human SK-MEL-28 melanoma cell lines.	2005 Oct	16142328
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	18064767
Effects of common antitussive drugs on the hERG potassium channel current.	2008 Dec	19034038
[Quantification of pentoxyverine citrate in human plasma by LC-ESI/MS method and its application].	2009 Dec	21351477

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

PENTOXYVERINE CITRATE

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

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

2-(2-(DIETHYLAMINO)ETHOXY)ETHYL 1-PHENYLCYCLOPENTANECARBOXYLATE CITRATE (1:1)

Systematic Name

English

Pentoxyverine citrate [WHO-DD]

Common 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