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

Details

Stereochemistry ACHIRAL
Molecular Formula C15H17NS2.C14H10O4
Molecular Weight 517.659
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIPEPIDINE HIBENZATE

SMILES

CN1CCCC(C1)=C(C2=CC=CS2)C3=CC=CS3.OC(=O)C4=C(C=CC=C4)C(=O)C5=CC=C(O)C=C5

InChI

InChIKey=KEEAAKGKVVTPOM-UHFFFAOYSA-N
InChI=1S/C15H17NS2.C14H10O4/c1-16-8-2-5-12(11-16)15(13-6-3-9-17-13)14-7-4-10-18-14;15-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)14(17)18/h3-4,6-7,9-10H,2,5,8,11H2,1H3;1-8,15H,(H,17,18)

HIDE SMILES / InChI

Molecular Formula C14H10O4
Molecular Weight 242.2268
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H17NS2
Molecular Weight 275.432
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Doses

AEs

PubMed

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
Record UNII
78578GFU8W
Record Status Validated (UNII)
Record Version