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
A non-potentiometric sensing method for the determination of pentoxyverine with PQC sensors based on ion-pair complexes.	2001 Dec	11783787
Effects of common antitussive drugs on the hERG potassium channel current.	2008 Dec	19034038

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