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
Structure for Metiamide (DB08805)
- Weight
- Average: 244.38
Monoisotopic: 244.081637912 - Chemical Formula
- C9H16N4S2
- Synonyms
- Methiamide
- Metiamida
- Metiamide
- Metiamidum
- External IDs
- SK&F 92058
- SKF 92058
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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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.
Target Actions Organism AHistamine H2 receptor antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Metiamide Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmphetamine Amphetamine may decrease the sedative activities of Metiamide. Amprenavir Metiamide can cause a decrease in the absorption of Amprenavir resulting in a reduced serum concentration and potentially a decrease in efficacy. Asunaprevir Metiamide can cause a decrease in the absorption of Asunaprevir resulting in a reduced serum concentration and potentially a decrease in efficacy. Atazanavir Metiamide can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy. Benzphetamine Benzphetamine may decrease the sedative activities of Metiamide. Benzylpenicilloyl polylysine Metiamide may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. Betahistine The therapeutic efficacy of Betahistine can be decreased when used in combination with Metiamide. Bifonazole Metiamide can cause a decrease in the absorption of Bifonazole resulting in a reduced serum concentration and potentially a decrease in efficacy. Bisacodyl The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Metiamide. Bosutinib Metiamide can cause a decrease in the absorption of Bosutinib resulting in a reduced serum concentration and potentially a decrease in efficacy. 
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- 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
- External Links
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0.50 HANSCH,C & LEO,AJ (1985) - Predicted Properties
Property Value Source Water Solubility 0.0287 mg/mL ALOGPS logP 0.5 ALOGPS logP 0.34 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.34 Chemaxon pKa (Strongest Basic) 6.91 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 52.74 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 70.4 m3·mol-1 Chemaxon Polarizability 27.19 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9321 Blood Brain Barrier + 0.8686 Caco-2 permeable - 0.56 P-glycoprotein substrate Substrate 0.7606 P-glycoprotein inhibitor I Non-inhibitor 0.8835 P-glycoprotein inhibitor II Non-inhibitor 0.9829 Renal organic cation transporter Non-inhibitor 0.5167 CYP450 2C9 substrate Non-substrate 0.8006 CYP450 2D6 substrate Non-substrate 0.8241 CYP450 3A4 substrate Non-substrate 0.6444 CYP450 1A2 substrate Non-inhibitor 0.6219 CYP450 2C9 inhibitor Non-inhibitor 0.7993 CYP450 2D6 inhibitor Non-inhibitor 0.8256 CYP450 2C19 inhibitor Non-inhibitor 0.5201 CYP450 3A4 inhibitor Non-inhibitor 0.7244 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.821 Ames test Non AMES toxic 0.6875 Carcinogenicity Non-carcinogens 0.962 Biodegradation Not ready biodegradable 0.9856 Rat acute toxicity 2.2016 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7683 hERG inhibition (predictor II) Non-inhibitor 0.7285
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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 diff...
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- 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]
Drug created at October 15, 2010 22:20 / Updated at February 21, 2021 18:52