TIOTIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16N8S2
Molecular Weight	312.418
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(NCCSCC1=CSC(NC(N)=N)=N1)=NC#N

InChI

InChIKey=YDDXVAXDYKBWDX-UHFFFAOYSA-N

InChI=1S/C10H16N8S2/c1-14-9(16-6-11)15-2-3-19-4-7-5-20-10(17-7)18-8(12)13/h5H,2-4H2,1H3,(H2,14,15,16)(H4,12,13,17,18)

HIDE SMILES / InChI

Molecular Formula	C10H16N8S2
Molecular Weight	312.418
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12869657 | https://www.ncbi.nlm.nih.gov/pubmed/6107146 | https://www.ncbi.nlm.nih.gov/pubmed/6113920 | Testa, B. (2013) Advances in Drug Research, v.20, page 280, retrieved from: https://books.google.ru/books?id=wRMlBQAAQBAJ

Tiotidine is a controversial histamine H2 receptor ligand with negligible activity against H1- and H3- receptors. It was found that tiotidine behaves as an inverse agonist in U-937 cells, diminishing basal cAMP levels. Tiotidine showed two binding sites, one with high affinity and low capacity and the other with low affinity and high capacity. Tiotidine is currently in use as a radioligand in histamine H2-receptor binding studies. Compared to cimetidine, tiotidine appears to be approximately eight times more potent on a molar basis than cimetidine as an inhibitor of acid secretion, and the tiotidine effect is more prolonged. It was developed for the treatment of peptic ulcer.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Inverse Agonist 85		22.0 nM [IC50]

PubMed

Title	Date	PubMed
Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors.	2006-04	16354729
Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation.	2005-11	15961859
Effects of cimetidine-like drugs on recombinant GABAA receptors.	2004-10-08	15363660
Tiotidine, a histamine H2 receptor inverse agonist that binds with high affinity to an inactive G-protein-coupled form of the receptor. Experimental support for the cubic ternary complex model.	2003-08	12869657
Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells.	2003	14671421
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.	2002-06	12065605
Effects of N-alpha-methyl-histamine on human H(2) receptors expressed in CHO cells.	2002-06	12010879
Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation.	2001-04-02	11306145
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.	1997-11	9384502

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:10:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:45 GMT 2025`
Record UNII	EZU9AIZ69M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ICI 125,211

Preferred Name

English

TIOTIDINE

Official Name

English

ICI-125,211

Code

English

ICI-125211

Code

English

TIOTIDINE [USAN]

Common Name

English

2-Cyano-1-[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]ethyl]-3-methylguanidine

Systematic Name

English

GUANIDINE, N''-CYANO-N-(2-(((2-((DIAMINOMETHYLENE)AMINO)-4-THIAZOLYL)METHYL)THIO)ETHYL)-N'-METHYL-

Systematic Name

English

tiotidine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29702