U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H17NS2.C6H8O7
Molecular Weight 467.556
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIPEPIDINE CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1CCCC(C1)=C(C2=CC=CS2)C3=CC=CS3

InChI

InChIKey=WQOYJMWVNIGIQR-UHFFFAOYSA-N
InChI=1S/C15H17NS2.C6H8O7/c1-16-8-2-5-12(11-16)15(13-6-3-9-17-13)14-7-4-10-18-14;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-4,6-7,9-10H,2,5,8,11H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.journalmc.org/index.php/JMC/article/viewFile/1564/916

Tipepidine (INN) also known as tipepidine hibenzate (JAN), is a synthetic, non-opioid antitussive and expectorant of the thiambutene class. The drug was discovered in the 1950s, and was developed in Japan in 1959. It is used as the hibenzate and citrate salts. The safety of tipepidine in children and adults has already been established. It is reported that tipepidine inhibits G-protein-coupled inwardly rectifying potassium (GIRK)-channel currents. The inhibition of GIRK channels by tipepidine is expected to modulate the level of monoamines in the brain. Tipepidine can improve attention deficit/hyperactivity disorder (ADHD) symptoms by modulating monoaminergic neurotransmission through the inhibition of GIRK channels. Tipepidine also is being investigated in depression, obsessive-compulsive disorder, and attention-deficit hyperactivity disorder (ADHD). As it acts on the central nervous system, overdose can cause altered mental status and other neurological symptoms; however, there have been few reports of tipepidine intoxication, including six cases in children and no cases in adults.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The preparation of rapidly disintegrating tablets in the mouth.
2001 Nov
The centrally acting non-narcotic antitussive tipepidine produces antidepressant-like effect in the forced swimming test in rats.
2009 Dec 14
Fixed drug eruption induced by tipepidine hibenzate.
2010 May
[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats].
2010 May
Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test.
2010 Sep 13
Patents

Patents

Sample Use Guides

tipepidine hibenzate taken orally at 30 mg/day for 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Submaximal contractions of bronchial muscle evoked by exogenous acetylcholine, ACh (1-30 microM) were inhibited by tipepidine (10-100 microM)
Name Type Language
TIPEPIDINE CITRATE
JAN   WHO-DD  
Common Name English
ASVERIN CITRATE
Common Name English
TIPEPIDINE CITRATE [JAN]
Common Name English
ASVERINE CITRATE
Common Name English
TIPEPIDINE MONOCITRATE
Common Name English
PIPERIDINE, 3-(DI-2-THIENYLMETHYLENE)-1-METHYL-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
1-METHYL-3-(DI-2-THIENYLMETHYLENE)PIPERIDINE CITRATE
Systematic Name English
Tipepidine citrate [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50163553
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY
SMS_ID
100000089906
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY
CAS
14698-07-8
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY
PUBCHEM
203585
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY
EVMPD
SUB25689
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY
FDA UNII
IPZ5GQ4MX4
Created by admin on Sat Dec 16 05:58:04 GMT 2023 , Edited by admin on Sat Dec 16 05:58:04 GMT 2023
PRIMARY