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Identification
NameMetiamide
Accession NumberDB08805
TypeSmall Molecule
GroupsExperimental
Description

Metiamide is a histamine H2-receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine.

Structure
Thumb
Synonyms
Methiamide
Metiamida
Metiamidum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3K7670861M
CAS number34839-70-8
WeightAverage: 244.38
Monoisotopic: 244.081637912
Chemical FormulaC9H16N4S2
InChI KeyInChIKey=FPBPLBWLMYGIQR-UHFFFAOYSA-N
InChI
InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)
IUPAC Name
3-methyl-1-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea
SMILES
CNC(=S)NCCSCC1=C(C)NC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as imidazoles. These are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Imidazole
  • Thiourea
  • Thiocarbonic acid derivative
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationPotential in the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
PharmacodynamicsMetiamide is a histamine H2-receptor antagonist. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin. Metiamide inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Metiamide include an increase in gastric bacterial flora such as nitrate-reducing organisms.
Mechanism of actionMetiamide binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Metiamide Action PathwayDrug actionSMP00735
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9321
Blood Brain Barrier+0.8686
Caco-2 permeable-0.56
P-glycoprotein substrateSubstrate0.7606
P-glycoprotein inhibitor INon-inhibitor0.8835
P-glycoprotein inhibitor IINon-inhibitor0.9829
Renal organic cation transporterNon-inhibitor0.5167
CYP450 2C9 substrateNon-substrate0.8006
CYP450 2D6 substrateNon-substrate0.8241
CYP450 3A4 substrateNon-substrate0.6444
CYP450 1A2 substrateNon-inhibitor0.6219
CYP450 2C9 inhibitorNon-inhibitor0.7993
CYP450 2D6 inhibitorNon-inhibitor0.8256
CYP450 2C19 inhibitorNon-inhibitor0.5201
CYP450 3A4 inhibitorNon-inhibitor0.7244
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.821
Ames testNon AMES toxic0.6875
CarcinogenicityNon-carcinogens0.962
BiodegradationNot ready biodegradable0.9856
Rat acute toxicity2.2016 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7683
hERG inhibition (predictor II)Non-inhibitor0.7285
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.50HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.0287 mg/mLALOGPS
logP0.5ALOGPS
logP0.34ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)6.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.74 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.4 m3·mol-1ChemAxon
Polarizability27.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Histamine receptor activity
Specific Function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) si...
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular Weight:
40097.65 Da
References
  1. Black JW, Duncan WA, Emmett JC, Ganellin CR, Hesselbo T, Parsons ME, Wyllie JH: Metiamide--an orally active histamine H2-receptor antagonist. 1973. Agents Actions. 1994 Dec;43(3-4):91-5; discussion 96. [PubMed:7725982 ]
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Drug created on October 15, 2010 16:20 / Updated on August 17, 2016 12:24