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Metiamide

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Identification

Generic Name
Metiamide
DrugBank Accession Number
DB08805
Background

Metiamide is an H-2 receptor antagonist derived from burimamide. It was an intermediate product on the path to developing cimetidine.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 244.38
Monoisotopic: 244.081637912
Chemical Formula
C9H16N4S2
Synonyms
  • Methiamide
  • Metiamida
  • Metiamide
  • Metiamidum
External IDs
  • SK&F 92058
  • SKF 92058
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Pharmacology

Indication

Potential in the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Metiamide 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 action

Metiamide 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.

TargetActionsOrganism
AHistamine H2 receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Metiamide Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AmphetamineAmphetamine may decrease the sedative activities of Metiamide.
AmprenavirMetiamide can cause a decrease in the absorption of Amprenavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
AsunaprevirMetiamide can cause a decrease in the absorption of Asunaprevir resulting in a reduced serum concentration and potentially a decrease in efficacy.
AtazanavirMetiamide can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
BenzphetamineBenzphetamine may decrease the sedative activities of Metiamide.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Imidazoles
Alternative Parents
Heteroaromatic compounds / Thioureas / Sulfenyl compounds / Dialkylthioethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Organosulfur compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles (CHEBI:6896)
Affected organisms
Not Available

Chemical Identifiers

UNII
3K7670861M
CAS number
34839-70-8
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0061722
KEGG Drug
D05004
KEGG Compound
C07449
PubChem Compound
1548992
PubChem Substance
99445275
ChemSpider
1265996
BindingDB
50000382
ChEBI
6896
ChEMBL
CHEMBL275446
ZINC
ZINC000005424950
Guide to Pharmacology
GtP Drug Page
Wikipedia
Metiamide

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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)13.34Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0005-9300000000-907f73f8f938674a5458
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1290000000-c04e585624b89983a909
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a5c-9220000000-88a86c05031f40b5015f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-9520000000-bf26685631bec9ea8a57
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01e9-9400000000-0aa9cd01961533c3e420
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-9310000000-215e337da082fabba7a3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-9100000000-fc727109373e6e56d611
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.3984153
predicted
DarkChem Lite v0.1.0
[M-H]-158.2479153
predicted
DarkChem Lite v0.1.0
[M-H]-147.2531
predicted
DeepCCS 1.0 (2019)
[M+H]+159.9766153
predicted
DarkChem Lite v0.1.0
[M+H]+159.4749153
predicted
DarkChem Lite v0.1.0
[M+H]+150.55013
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.2184153
predicted
DarkChem Lite v0.1.0
[M+Na]+159.2478153
predicted
DarkChem Lite v0.1.0
[M+Na]+159.90343
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histamine H2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General 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) signaling pathway (By similarity)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
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. [Article]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 15, 2010 22:20 / Updated at February 21, 2021 18:52