TIARAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18ClN3O3S
Molecular Weight	355.84
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCN1CCN(CC1)C(=O)CN2C(=O)SC3=C2C=C(Cl)C=C3

InChI

InChIKey=HTJXMOGUGMSZOG-UHFFFAOYSA-N

InChI=1S/C15H18ClN3O3S/c16-11-1-2-13-12(9-11)19(15(22)23-13)10-14(21)18-5-3-17(4-6-18)7-8-20/h1-2,9,20H,3-8,10H2

HIDE SMILES / InChI

Description
Sources: https://www.astellas.com/en/csr/pdf/astellas_csr2011v3_eg.pdf | http://image.packageinsert.jp/pdf.php?mode=1&yjcode=1148001F1059

Tiaramide is an anti-inflammatory and analgesic drug, which was developed by Fujisawa Pharmaceutical (now Astellas pharma) and used in Japan under the name Solantol for the treatment of different pain and inflammatory disorders. Later on, Astellas recalled the product by reasons other than safety. The mechanism of tiaramide action is unknown.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://image.packageinsert.jp/pdf.php?mode=1&yjcode=1148001F1059	Primary		Approved 8429	SOLANTAL Approved Use Pain management after surgery, tooth extraction and trauma, pain relief in arthritis, low back pain, cervical shoulder arm syndrome, pelvic inflammation, birth canal injuries, breast engorgement, herpes zoster, polymorphic exudative erythema, cystitis, epididymitis, uveitis, pericoronitis, acute upper respiratory tract inflammation. Launch Date 1974
Inflammatory diseases 12 Sources: http://image.packageinsert.jp/pdf.php?mode=1&yjcode=1148001F1059	Palliative		Approved 8429	SOLANTOL Approved Use Pain management after surgery, tooth extraction and trauma, pain relief in arthritis, low back pain, cervical shoulder arm syndrome, pelvic inflammation, birth canal injuries, breast engorgement, herpes zoster, polymorphic exudative erythema, cystitis, epididymitis, uveitis, pericoronitis, acute upper respiratory tract inflammation. Launch Date 1974

PubMed

Title	Date	PubMed
Strategy for structure elucidation of drug metabolites derived from protonated molecules and (MS)n fragmentation of zotepine, tiaramide and their metabolites.	2002	15618683
Synthesis and anti-inflammatory activity of certain piperazinylthienylpyridazine derivatives.	2007 Jul	17703729
Safety of selective cyclooxygenase-2 inhibitors and a basic non-steroidal anti-inflammatory drug (NSAID) in Japanese patients with NSAID-induced urticaria and/or angioedema: Comparison of meloxicam, etodolac and tiaramide.	2007 Mar	17291297
Evaluation of the interaction between nonsteroidal anti-inflammatory drugs and methotrexate using human organic anion transporter 3-transfected cells.	2008 Oct 31	18789319

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 1 tablet (100 mg) once daily. In patients with acute upper respiratory tract inflammation the dose may be increased up to 3 tablets.

Route of Administration: Oral

In Vitro Use Guide

Tiaramide in 10(-4) and 10(-5)M inhibited effectively the platelet aggregation caused by ADP.

Name

Type

Language

TIARAMIDE

Official Name

English

RHC 2592A

Code

English

1-PIPERAZINEETHANOL, 4-((5-CHLORO-2-OXO-3(2H)-BENZOTHIAZOLYL)ACETYL)

Common Name

English

2(3H)-BENZOTHIAZOLONE, 5-CHLORO-3-(2-(4-(2-HYDROXYETHYL)-1-PIPERAZINYL)-2-OXOETHYL)-

Systematic Name

English

TIARAMIDE [MI]

Common Name

English

Tiaramide [WHO-DD]

Common Name

English

RHC-2592A

Code

English

tiaramide [INN]

Common Name

English

TIALAMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319