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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 of TIOTIDINE

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
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

Targets

Primary TargetPharmacologyConditionPotency
22.0 nM [IC50]
PubMed

PubMed

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

Patents

Name Type Language
TIOTIDINE
INN   USAN  
INN   USAN  
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
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152643
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
EVMPD
SUB11093MIG
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046341
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
SMS_ID
100000077255
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
MESH
C023990
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
CAS
69014-14-8
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
PUBCHEM
50287
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
FDA UNII
EZU9AIZ69M
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
INN
4895
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL269646
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
PRIMARY