TIPEPIDINE CITRATE

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 Search

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

Molecular Formula	C15H17NS2
Molecular Weight	275.432
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24493927
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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GIRK channels 4 Target ID: GIRK channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/18825343	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Attention deficit hyperactivity disorder 70 Sources: http://www.ncbi.nlm.nih.gov/pubmed/24493927	Primary		Phase II 1147	Unknown Approved Use Unknown
Treatment-resistant depression 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26189506	Primary		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
30 mg 2 times / day multiple, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33247483/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33247483/	Sources: https://pubmed.ncbi.nlm.nih.gov/33247483/
100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, CHILD Health Status: unknown Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	Disc. AE: Deliria, Excitement... AEs leading to discontinuation/dose reduction: Deliria Excitement Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/
11 mg/kg single, oral Overdose Dose: 11 mg/kg Route: oral Route: single Dose: 11 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, UNKNOWN Health Status: unknown Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	Disc. AE: Deliria, Hallucination... AEs leading to discontinuation/dose reduction: Deliria Hallucination Confusion Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/

AEs

AE	Significance	Dose	Population
Deliria	Disc. AE	100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, CHILD Health Status: unknown Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/
Excitement	Disc. AE	100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, CHILD Health Status: unknown Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/
Confusion	Disc. AE	11 mg/kg single, oral Overdose Dose: 11 mg/kg Route: oral Route: single Dose: 11 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, UNKNOWN Health Status: unknown Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/
Deliria	Disc. AE	11 mg/kg single, oral Overdose Dose: 11 mg/kg Route: oral Route: single Dose: 11 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, UNKNOWN Health Status: unknown Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/
Hallucination	Disc. AE	11 mg/kg single, oral Overdose Dose: 11 mg/kg Route: oral Route: single Dose: 11 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/	unknown, UNKNOWN Health Status: unknown Age Group: UNKNOWN Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21955016/

PubMed

Title	Date	PubMed
Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test.	2010-09-13	20621160
Fixed drug eruption induced by tipepidine hibenzate.	2010-05	20536661
[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats].	2010-05	20460867
The centrally acting non-narcotic antitussive tipepidine produces antidepressant-like effect in the forced swimming test in rats.	2009-12-14	19616036
The preparation of rapidly disintegrating tablets in the mouth.	2001-11	11775950

Patents

Sample Use Guides

In Vivo Use Guide

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)

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:34:59 GMT 2025` Edited by `admin` on `Mon Mar 31 21:34:59 GMT 2025`
Record UNII	IPZ5GQ4MX4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIPEPIDINE CITRATE

Common Name

English

ASVERIN CITRATE

Preferred 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