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

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 80		22.0 nM [IC50]

PubMed

Title	Date	PubMed
Heterologous expression of rat epitope-tagged histamine H2 receptors in insect Sf9 cells.	1997 Nov	9384502
Inhibition of effects of endogenously synthesized histamine disturbs in vitro human dendritic cell differentiation.	2001 Apr 2	11306145
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.	2002 Jun	12065605
Effects of N-alpha-methyl-histamine on human H(2) receptors expressed in CHO cells.	2002 Jun	12010879
Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells.	2003	14671421
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 Aug	12869657
Effects of cimetidine-like drugs on recombinant GABAA receptors.	2004 Oct 8	15363660
Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation.	2005 Nov	15961859
Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors.	2006 Apr	16354729

Patents

Name

Type

Language

TIOTIDINE

Official Name

English

ICI-125,211

Code

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