Identification
- Summary
Cimetidine is a histamine H2 receptor antagonist used to manage GERD, peptic ulcer disease, and indigestion.
- Brand Names
- Good Sense Heartburn Relief, Tagamet
- Generic Name
- Cimetidine
- DrugBank Accession Number
- DB00501
- Background
A histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cimetidine (DB00501)
- Weight
- Average: 252.339
Monoisotopic: 252.115715232 - Chemical Formula
- C10H16N6S
- Synonyms
- 1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine
- 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine
- Cimetidin
- Cimetidina
- Cimétidine
- Cimetidine
- Cimetidinum
- N-cyano-N'-methyl-N''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine
- N''-cyano-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine
- External IDs
- NSC-335308
- SKF 92334
- SKF-92334
Pharmacology
- Indication
Cimetidine is indicated to reduce gastric acid secretion and to treat the following disease states: duodenal ulcers, non-malignant gastric ulcers, gastroesophageal reflux disease, and pathological hypersecretion associated with Zollinger-Ellison Syndrome, systemic mastocytosis, and multiple endocrine adenomas.7 It is indicated for prophylaxis of recurrent gastric or duodenal ulcers, as adjunctive therapy in the management of cystic fibrosis in children, and to treat NSAID induced lesions and gastrointestinal symptoms.7
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in management of Cystic fibrosis (cf) •••••••••••• •••••••• •••••• Management of Gerd •••••••••••• •••••• Prevention of Gastrointestinal symptoms •••••••••••• •••••• Treatment of Gastrointestinal symptoms •••••••••••• •••••• Prevention of Heartburn ••• ••• •••••• - Contraindications & Blackbox Warnings
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Cimetidine 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. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.
- Mechanism of action
Cimetidine 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
Two peak plasma concentrations are often observed after oral administration of cimetidine, likely as a result of discontinuous absorption in the gastrointestinal tract.6 In healthy patients, the absolute bioavailability of cimetidine is approximately 60%; however, the bioavailability can be as high as 70% in patients with peptic ulcer disease.6 Overall, rates of bioavailability are much more variable in patients with peptic ulcer disease.6
- Volume of distribution
The volume of distribution of cimetidine is reported to be 1 L/kg.6
- Protein binding
In humans, approximately 22.5% of cimetidine is plasma protein bound.7
- Metabolism
After intravenous administration of cimetidine, the majority of the parent drug (58-77%) is eliminated unchanged in the urine.2,7 Cimetidine’s primary metabolite is cimetidine sulfoxide and represents an estimated 10-15% of total elimination.2,6 Researchers have also identified a minor cimetidine metabolite with a hydroxylated methyl group on the imidazole ring which represents only 4% of total elimination.2,6 Both cytochrome P450 enzymes and flavin-containing monooxygenases are implicated in the metabolism of cimetidine, although it is unclear which specific enzymes are involved.3 Cimetidine is a well known enzyme inhibitor and may impair the metabolism of certain co-administered medications.4
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- Route of elimination
Cimetidine is excreted primarily in the urine.7
- Half-life
Cimetidine's half-life is estimated to be around 2 hours.7
- Clearance
Cimetidine's reported systemic clearance value is approximately 500-600 ml/min.6
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
In the rare event of cimetidine overdose, it is vital to maintain the airway and cardiovascular status.5 The patient should be closely monitored and provided with symptomatic and supportive treatment as needed.5 Interventions such as gastric lavage and administration of activated charcoal may be initiated if deemed appropriate and necessary.5
- Pathways
Pathway Category Cimetidine Action Pathway Drug action Cimetidine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAbacavir Cimetidine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Cimetidine. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Cimetidine. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Cimetidine. Acamprosate The excretion of Acamprosate can be decreased when combined with Cimetidine. - Food Interactions
- Take with food. Food increases bioavailability. For prophylaxis of gastric symptoms, take cimetidine 30-60 minutes prior to food administration.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cimetidine hydrochloride WF10491673 70059-30-2 QJHCNBWLPSXHBL-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Cimetag (Julphar) / Tagamet HB 200 (GlaxoSmithKline) / Tagamet HB200 (GlaxoSmithKline) / Ulcedine / Ulcerfen (Finadiet) / Ulcimet (Farmasa)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cimetidine Tablet 300 mg Oral Aa Pharma Inc 1982-12-31 Not applicable Canada 
Cimetidine Tablet 200 mg Oral Aa Pharma Inc 1982-12-31 Not applicable Canada Cimetidine Tablet 800 mg Oral Aa Pharma Inc 1988-12-31 Not applicable Canada Cimetidine Tablet 600 mg Oral Aa Pharma Inc 1983-12-31 Not applicable Canada Cimetidine Tablet, film coated 200 mg/1 Oral TEVA PHARMACEUTICALS USA 2006-11-28 2006-11-28 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-cimetidine Oral Solution Liquid 300 mg / 5 mL Oral Apotex Corporation 2001-01-05 Not applicable Canada Cimetidine Tablet, film coated 300 mg/1 Oral Carilion Materials Management 2003-11-24 Not applicable US 
Cimetidine Tablet, film coated 400 mg/1 Oral Nucare Pharmaceuticals, Inc. 2004-02-02 2018-12-31 US Cimetidine Injection, solution 150 mg/1mL Intramuscular; Intravenous Hospira, Inc. 1995-01-31 2010-09-01 US Cimetidine Tablet, film coated 800 mg/1 Oral Physicians Total Care, Inc. 1994-05-23 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acid Reducer Tablet 200 mg/1 Oral Rite Aid 2005-07-08 2014-07-27 US Acid Reducer Tablet, film coated 200 mg/1 Oral Kroger Company 2015-10-21 Not applicable US Basic Care Acid Reducer Tablet, film coated 200 mg/1 Oral Amazon.com Services LLC 2022-01-09 Not applicable US Cimetidine Acid Reducer Tablet, film coated 200 mg/1 Oral Walgreen Company 2001-03-27 Not applicable US DG Health Heartburn Relief Tablet 200 mg/1 Oral Dolgencorp 2010-03-02 2014-08-18 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cimetidine 10% / Lidocaine 5% / Salicylic Acid 40% Cimetidine (10 g/100g) + Lidocaine (5 g/100g) + Salicylic acid (40 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Cimetidine 5% / Ibuprofen 2% / Salicylic Acid 17% Cimetidine (5 g/100g) + Ibuprofen (2 g/100g) + Salicylic acid (17 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-17 Not applicable US
Categories
- ATC Codes
- A02BA51 — Cimetidine, combinations
- A02BA — H2-receptor antagonists
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Acid Reducers
- Adjuvants
- Agents Causing Muscle Toxicity
- Alimentary Tract and Metabolism
- Amidines
- Anti-Ulcer Agents
- BSEP/ABCB11 Inhibitors
- Chemically-Induced Disorders
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (moderate)
- Cytochrome P-450 CYP3A5 Inhibitors (weak)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (moderate)
- Cytochrome P-450 Enzyme Inhibitors
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Guanidines
- Histamine Agents
- Histamine Antagonists
- Histamine H2 Antagonists
- Imidazoles
- MATE 1 Inhibitors
- MATE 1 Substrates
- MATE 2 Inhibitors
- MATE 2 Substrates
- MATE inhibitors
- MATE substrates
- Neurotransmitter Agents
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- OCT1 inhibitors
- OCT1 substrates
- OCT2 Inhibitors
- OCT2 Substrates
- P-glycoprotein inducers
- P-glycoprotein substrates
- 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 / Guanidines / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Dialkylthioethers / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Imines / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carboximidamide / Dialkylthioether / Guanidine / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imine / Organic 1,3-dipolar compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles, guanidines, aliphatic sulfide, nitrile (CHEBI:3699)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 80061L1WGD
- CAS number
- 51481-61-9
- InChI Key
- AQIXAKUUQRKLND-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
- IUPAC Name
- (Z)-N''-cyano-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
- SMILES
- CN\C(NCCSCC1=C(C)NC=N1)=N\C#N
References
- Synthesis Reference
Saburo Uchikuga, Tomoyasu Tashiro, Yasuko Osawa, "Process for preparing the H.sub.2 -receptor antagonist cimetidine." U.S. Patent US4413129, issued March, 1972.
US4413129- General References
- Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. [Article]
- Larsson R, Erlanson P, Bodemar G, Walan A, Bertler A, Fransson L, Norlander B: The pharmacokinetics of cimetidine and its sulphoxide metabolite in patients with normal and impaired renal function. Br J Clin Pharmacol. 1982 Feb;13(2):163-70. doi: 10.1111/j.1365-2125.1982.tb01351.x. [Article]
- Lu X, Li C, Fleisher D: Cimetidine sulfoxidation in small intestinal microsomes. Drug Metab Dispos. 1998 Sep;26(9):940-2. [Article]
- Hoensch HP, Hutzel H, Kirch W, Ohnhaus EE: Isolation of human hepatic microsomes and their inhibition by cimetidine and ranitidine. Eur J Clin Pharmacol. 1985;29(2):199-206. doi: 10.1007/BF00547422. [Article]
- Pino MA, Azer SA: Cimetidine . [Article]
- Somogyi A, Gugler R: Clinical pharmacokinetics of cimetidine. Clin Pharmacokinet. 1983 Nov-Dec;8(6):463-95. doi: 10.2165/00003088-198308060-00001. [Article]
- DPD Approved Drug Products: Cimetidine (200, 300, 400, 600, 800 mg) [Link]
- External Links
- Human Metabolome Database
- HMDB0014644
- KEGG Drug
- D00295
- KEGG Compound
- C06952
- PubChem Compound
- 2756
- PubChem Substance
- 46505360
- ChemSpider
- 2654
- BindingDB
- 50103595
- 2541
- ChEBI
- 3699
- ChEMBL
- CHEMBL30
- ZINC
- ZINC000018115268
- Therapeutic Targets Database
- DAP000338
- PharmGKB
- PA449001
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cimetidine
- MSDS
- Download (73.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Healthy Subjects (HS) 1 4 Completed Prevention Aspiration of Gastric Contents 1 4 Recruiting Basic Science Breast Milk Production 1 3 Completed Prevention Peptic ulcer haemorrhage 1 3 Completed Prevention Stress Ulcer Prophylaxis 1
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Apotex inc
- Contract pharmacal corp
- Dava pharmaceuticals inc
- Endo pharmaceuticals inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Lek pharmaceuticals d d
- Mylan pharmaceuticals inc
- L perrigo co
- Perrigo co
- Pliva inc
- Roxane laboratories inc
- Sandoz inc
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- Hospira inc
- Luitpold pharmaceuticals inc
- Teva parenteral medicines inc
- Actavis mid atlantic llc
- Duramed pharmaceuticals inc sub barr laboratories inc
- Hi tech pharmacal co inc
- Novex pharma
- Pharmaceutical assoc inc div beach products
- Teva pharmaceuticals usa
- Wockhardt eu operations (swiss) ag
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotex Inc.
- Apotheca Inc.
- A-S Medication Solutions LLC
- Baxter International Inc.
- Bristol-Myers Squibb Co.
- Bryant Ranch Prepack
- Cardinal Health
- Central Texas Community Health Centers
- Comprehensive Consultant Services Inc.
- Darby Dental Supply Co. Inc.
- DAVA Pharmaceuticals
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Endo Pharmaceuticals Inc.
- GlaxoSmithKline Inc.
- Group Health Cooperative
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Hi Tech Pharmacal Co. Inc.
- Hospira Inc.
- Ivax Pharmaceuticals
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Lek Pharmaceuticals Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novex Pharma
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Perrigo Co.
- Pharma Pac LLC
- Pharmaceutical Association
- Pharmedix
- Pharmpak Inc.
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescription Dispensing Service Inc.
- Qualitest
- Rebel Distributors Corp.
- Sandhills Packaging Inc.
- Sanofi-Aventis Inc.
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Teva Pharmaceutical Industries Ltd.
- Torpharm Inc.
- Tya Pharmaceuticals
- UDL Laboratories
- United Research Laboratories Inc.
- Va Cmop Dallas
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Suspension Oral Tablet, film coated Oral Solution Parenteral 300.000 mg Tablet Oral 400.000 mg Tablet, film coated Oral 800 mg Tablet, coated Oral Tablet, effervescent 200 MG Tablet, coated Oral 800 MG Solution Oral 400 mg/6.67mL Tablet Oral Tablet Oral 300 mg/1 Tablet Oral 300 mg Tablet Oral 400 mg/1 Tablet Oral 600 mg Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 400 mg/1 Tablet, film coated Oral 800 mg/1 Cream Topical Tablet, film coated Oral 400.00 mg Gel Topical Injection, solution Intramuscular; Intravenous 150 mg/1mL Solution Oral 300 mg/5mL Injection, solution Intravenous 6 mg/1mL Tablet Oral 200 mg / tab Tablet Oral 800 mg / tab Injection Intravenous Tablet, effervescent Oral 200 MG Tablet, effervescent Syrup Tablet Oral 100 mg Tablet Oral 200 mg/1 Solution Intramuscular; Intravenous 150 mg / mL Tablet Oral 200 MG Injection Intramuscular; Intravenous 150 mg/ml Tablet, soluble Granule, for suspension Oral Injection, solution Tablet, delayed release Oral 800 mg Liquid Intravenous 6 mg / mL Liquid Intramuscular; Intravenous 150 mg / mL Liquid Oral 300 mg / 5 mL Liquid Oral 60 mg / mL Pill Powder Capsule Granule, for solution Oral Granule, for solution Oral 800 mg Injection Intramuscular Tablet Oral 800 mg Solution 150 mg/1ml Tablet, coated Oral 400 mg Tablet, coated Oral 200 mg Tablet Oral 400 mg Capsule 200 mg Suspension Oral 50 mg/5mL Tablet, film coated Oral 200 mg Tablet, film coated Oral 400 mg Solution 100 mg/1ml - Prices
Unit description Cost Unit Cimetidine 800 mg tablet 2.7USD tablet Tagamet 400 mg tablet 2.51USD tablet Cimetidine 150 mg/ml vial 1.67USD ml Cimetidine powder 1.48USD g Cimetidine 400 mg tablet 1.44USD tablet Tagamet 300 mg tablet 1.28USD tablet Cimetidine 300 mg tablet 0.93USD tablet Cimetidine 200 mg tablet 0.46USD tablet Cimetidine HCl 300 mg/5ml Solution 0.38USD ml Tagamet hb 200 mg tablet 0.37USD tablet Apo-Cimetidine 800 mg Tablet 0.27USD tablet Mylan-Cimetidine 800 mg Tablet 0.27USD tablet Acid reducer 200 mg tablet 0.21USD tablet Apo-Cimetidine 600 mg Tablet 0.18USD tablet Mylan-Cimetidine 600 mg Tablet 0.18USD tablet Novo-Cimetine 600 mg Tablet 0.18USD tablet Nu-Cimet 600 mg Tablet 0.18USD tablet Apo-Cimetidine 400 mg Tablet 0.14USD tablet Mylan-Cimetidine 400 mg Tablet 0.14USD tablet Novo-Cimetine 400 mg Tablet 0.14USD tablet Nu-Cimet 400 mg Tablet 0.14USD tablet Apo-Cimetidine 200 mg Tablet 0.09USD tablet Apo-Cimetidine 300 mg Tablet 0.09USD tablet Mylan-Cimetidine 300 mg Tablet 0.09USD tablet Novo-Cimetine 300 mg Tablet 0.09USD tablet Nu-Cimet 300 mg Tablet 0.09USD tablet Heartburn relief 200 mg tablet 0.08USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 142 °C PhysProp water solubility 9380 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001) logP 0.40 HANSCH,C ET AL. (1995) logS -1.35 ADME Research, USCD Caco2 permeability -5.89 ADME Research, USCD pKa 6.8 TOMLINSON,E & HAFKENSCHEID,TL (1986) - Predicted Properties
Property Value Source logP -0.11 Chemaxon pKa (Strongest Acidic) 13.38 Chemaxon pKa (Strongest Basic) 6.91 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 88.89 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 70.32 m3·mol-1 Chemaxon Polarizability 27.28 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 + 0.9855 Blood Brain Barrier - 0.6782 Caco-2 permeable - 0.6358 P-glycoprotein substrate Substrate 0.7887 P-glycoprotein inhibitor I Non-inhibitor 0.8781 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Inhibitor 0.7233 CYP450 2C9 substrate Non-substrate 0.8048 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5795 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.5773 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9575 Ames test Non AMES toxic 0.837 Carcinogenicity Non-carcinogens 0.9579 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.7341 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7983 hERG inhibition (predictor II) Non-inhibitor 0.8745
Spectra
- Mass Spec (NIST)
- Download (10 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.4053447 predictedDarkChem Lite v0.1.0 [M-H]- 165.8625447 predictedDarkChem Lite v0.1.0 [M-H]- 154.96318 predictedDeepCCS 1.0 (2019) [M-H]- 165.4053447 predictedDarkChem Lite v0.1.0 [M-H]- 165.8625447 predictedDarkChem Lite v0.1.0 [M-H]- 165.4053447 predictedDarkChem Lite v0.1.0 [M-H]- 165.8625447 predictedDarkChem Lite v0.1.0 [M-H]- 154.96318 predictedDeepCCS 1.0 (2019) [M-H]- 154.96318 predictedDeepCCS 1.0 (2019) [M+H]+ 166.5714447 predictedDarkChem Lite v0.1.0 [M+H]+ 166.9122447 predictedDarkChem Lite v0.1.0 [M+H]+ 157.32118 predictedDeepCCS 1.0 (2019) [M+H]+ 166.5714447 predictedDarkChem Lite v0.1.0 [M+H]+ 166.9122447 predictedDarkChem Lite v0.1.0 [M+H]+ 166.5714447 predictedDarkChem Lite v0.1.0 [M+H]+ 166.9122447 predictedDarkChem Lite v0.1.0 [M+H]+ 157.32118 predictedDeepCCS 1.0 (2019) [M+H]+ 157.32118 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.2492447 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.3485447 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.62956 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.2492447 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.3485447 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.2492447 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.3485447 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.62956 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.62956 predictedDeepCCS 1.0 (2019)
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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Hernandez-Munoz R, Montiel-Ruiz C, Vazquez-Martinez O: Gastric mucosal cell proliferation in ethanol-induced chronic mucosal injury is related to oxidative stress and lipid peroxidation in rats. Lab Invest. 2000 Aug;80(8):1161-9. [Article]
- Kuint J, Linder N, Reichman B: Hypoxemia associated with cimetidine therapy in a newborn infant. Am J Perinatol. 1996 Jul;13(5):301-3. [Article]
- Takahashi HK, Watanabe T, Yokoyama A, Iwagaki H, Yoshino T, Tanaka N, Nishibori M: Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol. 2006 Aug;70(2):450-3. Epub 2006 May 24. [Article]
- Pino MA, Azer SA: Cimetidine . [Article]
- Duda D, Lorenz W, Celik I: Histamine release in mesenteric traction syndrome during abdominal aortic aneurysm surgery: prophylaxis with H1 and H2 antihistamines. Inflamm Res. 2002 Oct;51(10):495-9. doi: 10.1007/pl00012418. [Article]
- Duda D, Lorenz W, Celik I: [Mesenteric traction syndrome during the operation of aneurysms of the abdominal aorta--histamine release and prophylaxis with antihistaminics]. Anaesthesiol Reanim. 2003;28(4):97-103. [Article]
- Kirch W, Hutt HJ, Heidemann H, Ramsch K, Janisch HD, Ohnhaus EE: Drug interactions with nitrendipine. J Cardiovasc Pharmacol. 1984;6 Suppl 7:S982-5. [Article]
- DPD Approved Drug Products: Cimetidine (200, 300, 400, 600, 800 mg) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid 11-beta-monooxygenase activity
- Specific Function
- Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
- Gene Name
- CYP11B1
- Uniprot ID
- P15538
- Uniprot Name
- Cytochrome P450 11B1, mitochondrial
- Molecular Weight
- 57572.44 Da
References
- Kenyon CJ, Fraser R, Birnie GG, Connell JM, Lever AF: Dose related in vitro effects of ranitidine and cimetidine on basal and ACTH-stimulated steroidogenesis. Gut. 1986 Oct;27(10):1143-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Ohashi K, Sakamoto K, Sudo T, Tateishi T, Fujimura A, Shiga T, Ebihara A: Effects of diltiazem and cimetidine on theophylline oxidative metabolism. J Clin Pharmacol. 1993 Dec;33(12):1233-7. [Article]
- Knodell RG, Browne DG, Gwozdz GP, Brian WR, Guengerich FP: Differential inhibition of individual human liver cytochromes P-450 by cimetidine. Gastroenterology. 1991 Dec;101(6):1680-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Trimethylamine monooxygenase activity
- Specific Function
- Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an impor...
- Gene Name
- FMO3
- Uniprot ID
- P31513
- Uniprot Name
- Dimethylaniline monooxygenase [N-oxide-forming] 3
- Molecular Weight
- 60032.975 Da
References
- Cashman JR: Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab. 2000 Sep;1(2):181-91. [Article]
- Cashman JR, Park SB, Berkman CE, Cashman LE: Role of hepatic flavin-containing monooxygenase 3 in drug and chemical metabolism in adult humans. Chem Biol Interact. 1995 Apr 28;96(1):33-46. [Article]
- Hai X, Adams E, Hoogmartens J, Van Schepdael A: Enantioselective in-line and off-line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin-containing monooxygenase genetic isoforms. Electrophoresis. 2009 Apr;30(7):1248-57. doi: 10.1002/elps.200800604. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Nadp binding
- Specific Function
- This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
- Gene Name
- FMO1
- Uniprot ID
- Q01740
- Uniprot Name
- Dimethylaniline monooxygenase [N-oxide-forming] 1
- Molecular Weight
- 60310.285 Da
References
- Hai X, Adams E, Hoogmartens J, Van Schepdael A: Enantioselective in-line and off-line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin-containing monooxygenase genetic isoforms. Electrophoresis. 2009 Apr;30(7):1248-57. doi: 10.1002/elps.200800604. [Article]
- Cashman JR: Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab. 2000 Sep;1(2):181-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Martinez C, Albet C, Agundez JA, Herrero E, Carrillo JA, Marquez M, Benitez J, Ortiz JA: Comparative in vitro and in vivo inhibition of cytochrome P450 CYP1A2, CYP2D6, and CYP3A by H2-receptor antagonists. Clin Pharmacol Ther. 1999 Apr;65(4):369-76. doi: 10.1016/S0009-9236(99)70129-3. [Article]
- Pino MA, Azer SA: Cimetidine . [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Martinez C, Albet C, Agundez JA, Herrero E, Carrillo JA, Marquez M, Benitez J, Ortiz JA: Comparative in vitro and in vivo inhibition of cytochrome P450 CYP1A2, CYP2D6, and CYP3A by H2-receptor antagonists. Clin Pharmacol Ther. 1999 Apr;65(4):369-76. doi: 10.1016/S0009-9236(99)70129-3. [Article]
- Orishiki M, Matsuo Y, Nishioka M, Ichikawa Y: In vivo administration of H2 blockers, cimetidine and ranitidine, reduced the contents of the cytochrome P450IID (CYP2D) subfamily and their activities in rat liver microsomes. Int J Biochem. 1994 Jun;26(6):751-8. [Article]
- Ishii Y, Nakamura K, Tsutsumi K, Kotegawa T, Nakano S, Nakatsuka K: Drug interaction between cimetidine and timolol ophthalmic solution: effect on heart rate and intraocular pressure in healthy Japanese volunteers. J Clin Pharmacol. 2000 Feb;40(2):193-9. [Article]
- Furuta S, Kamada E, Suzuki T, Sugimoto T, Kawabata Y, Shinozaki Y, Sano H: Inhibition of drug metabolism in human liver microsomes by nizatidine, cimetidine and omeprazole. Xenobiotica. 2001 Jan;31(1):1-10. doi: 10.1080/00498250110035615. [Article]
- Pino MA, Azer SA: Cimetidine . [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]
- Furuta S, Kamada E, Suzuki T, Sugimoto T, Kawabata Y, Shinozaki Y, Sano H: Inhibition of drug metabolism in human liver microsomes by nizatidine, cimetidine and omeprazole. Xenobiotica. 2001 Jan;31(1):1-10. doi: 10.1080/00498250110035615. [Article]
- Satoh T, Fujita KI, Munakata H, Itoh S, Nakamura K, Kamataki T, Itoh S, Yoshizawa I: Studies on the interactions between drugs and estrogen: analytical method for prediction system of gynecomastia induced by drugs on the inhibitory metabolism of estradiol using Escherichia coli coexpressing human CYP3A4 with human NADPH-cytochrome P450 reductase. Anal Biochem. 2000 Nov 15;286(2):179-86. doi: 10.1006/abio.1999.4775. [Article]
- Park EJ, Cho HY, Lee YB: Effect of Cimetidine and Phenobarbital on metabolite kinetics of Omeprazole in rats. Arch Pharm Res. 2005 Oct;28(10):1196-202. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Wang DS, Jonker JW, Kato Y, Kusuhara H, Schinkel AH, Sugiyama Y: Involvement of organic cation transporter 1 in hepatic and intestinal distribution of metformin. J Pharmacol Exp Ther. 2002 Aug;302(2):510-5. [Article]
- Satoh T, Fujita KI, Munakata H, Itoh S, Nakamura K, Kamataki T, Itoh S, Yoshizawa I: Studies on the interactions between drugs and estrogen: analytical method for prediction system of gynecomastia induced by drugs on the inhibitory metabolism of estradiol using Escherichia coli coexpressing human CYP3A4 with human NADPH-cytochrome P450 reductase. Anal Biochem. 2000 Nov 15;286(2):179-86. doi: 10.1006/abio.1999.4775. [Article]
- Park EJ, Cho HY, Lee YB: Effect of Cimetidine and Phenobarbital on metabolite kinetics of Omeprazole in rats. Arch Pharm Res. 2005 Oct;28(10):1196-202. [Article]
- Martinez C, Albet C, Agundez JA, Herrero E, Carrillo JA, Marquez M, Benitez J, Ortiz JA: Comparative in vitro and in vivo inhibition of cytochrome P450 CYP1A2, CYP2D6, and CYP3A by H2-receptor antagonists. Clin Pharmacol Ther. 1999 Apr;65(4):369-76. doi: 10.1016/S0009-9236(99)70129-3. [Article]
- Flockhart Table of Drug Interactions [Link]
- Drug Interactions & Labeling - FDA [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Martinez C, Albet C, Agundez JA, Herrero E, Carrillo JA, Marquez M, Benitez J, Ortiz JA: Comparative in vitro and in vivo inhibition of cytochrome P450 CYP1A2, CYP2D6, and CYP3A by H2-receptor antagonists. Clin Pharmacol Ther. 1999 Apr;65(4):369-76. doi: 10.1016/S0009-9236(99)70129-3. [Article]
- Flockhart Table of Drug Interactions [Link]
- Drug Interactions & Labeling - FDA [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Wilson CJ, Bogoyevitch MA, Winzor DJ: Interaction of cimetidine with human serum albumin. Biochem Pharmacol. 1990 Oct 1;40(7):1672-3. doi: 10.1016/0006-2952(90)90472-w. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [Article]
- Lentz KA, Polli JW, Wring SA, Humphreys JE, Polli JE: Influence of passive permeability on apparent P-glycoprotein kinetics. Pharm Res. 2000 Dec;17(12):1456-60. [Article]
- Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [Article]
- van der Sandt IC, Blom-Roosemalen MC, de Boer AG, Breimer DD: Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLC-PK1:MDR1 and Caco-2 cell lines. Eur J Pharm Sci. 2000 Sep;11(3):207-14. [Article]
- Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [Article]
- Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [Article]
- Taur JS, Rodriguez-Proteau R: Effects of dietary flavonoids on the transport of cimetidine via P-glycoprotein and cationic transporters in Caco-2 and LLC-PK1 cell models. Xenobiotica. 2008 Dec;38(12):1536-50. doi: 10.1080/00498250802499467. [Article]
- Choi YH, Yu AM: ABC transporters in multidrug resistance and pharmacokinetics, and strategies for drug development. Curr Pharm Des. 2014;20(5):793-807. doi: 10.2174/138161282005140214165212. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [Article]
- Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [Article]
- Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [Article]
- Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
- Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [Article]
- Pan BF, Sweet DH, Pritchard JB, Chen R, Nelson JA: A transfected cell model for the renal toxin transporter, rOCT2. Toxicol Sci. 1999 Feb;47(2):181-6. [Article]
- Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK(1) cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [Article]
- Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [Article]
- Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
- Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]
- Wang DS, Jonker JW, Kato Y, Kusuhara H, Schinkel AH, Sugiyama Y: Involvement of organic cation transporter 1 in hepatic and intestinal distribution of metformin. J Pharmacol Exp Ther. 2002 Aug;302(2):510-5. [Article]
- Lee WK, Reichold M, Edemir B, Ciarimboli G, Warth R, Koepsell H, Thevenod F: Organic cation transporters OCT1, 2, and 3 mediate high-affinity transport of the mutagenic vital dye ethidium in the kidney proximal tubule. Am J Physiol Renal Physiol. 2009 Jun;296(6):F1504-13. doi: 10.1152/ajprenal.90754.2008. Epub 2009 Apr 8. [Article]
- Song IS, Kong TY, Jeong HU, Kim EN, Kwon SS, Kang HE, Choi SZ, Son M, Lee HS: Evaluation of the transporter-mediated herb-drug interaction potential of DA-9801, a standardized dioscorea extract for diabetic neuropathy, in human in vitro and rat in vivo. BMC Complement Altern Med. 2014 Jul 17;14:251. doi: 10.1186/1472-6882-14-251. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Toxin transporter activity
- Specific Function
- Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
- Gene Name
- SLC22A3
- Uniprot ID
- O75751
- Uniprot Name
- Solute carrier family 22 member 3
- Molecular Weight
- 61279.485 Da
References
- Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [Article]
- Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [Article]
- Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [Article]
- Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]
- Chen L, Pawlikowski B, Schlessinger A, More SS, Stryke D, Johns SJ, Portman MA, Chen E, Ferrin TE, Sali A, Giacomini KM: Role of organic cation transporter 3 (SLC22A3) and its missense variants in the pharmacologic action of metformin. Pharmacogenet Genomics. 2010 Nov;20(11):687-99. doi: 10.1097/FPC.0b013e32833fe789. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [Article]
- Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
- Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
- Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
- Nagata Y, Kusuhara H, Endou H, Sugiyama Y: Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. Mol Pharmacol. 2002 May;61(5):982-8. [Article]
- Burckhardt BC, Brai S, Wallis S, Krick W, Wolff NA, Burckhardt G: Transport of cimetidine by flounder and human renal organic anion transporter 1. Am J Physiol Renal Physiol. 2003 Mar;284(3):F503-9. Epub 2002 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
- Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
- Motohashi H, Uwai Y, Hiramoto K, Okuda M, Inui K: Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). Eur J Pharmacol. 2004 Oct 25;503(1-3):25-30. [Article]
- Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [Article]
- Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
- Nagata Y, Kusuhara H, Endou H, Sugiyama Y: Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. Mol Pharmacol. 2002 May;61(5):982-8. [Article]
- Mori S, Takanaga H, Ohtsuki S, Deguchi T, Kang YS, Hosoya K, Terasaki T: Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells. J Cereb Blood Flow Metab. 2003 Apr;23(4):432-40. [Article]
- Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [Article]
- Bakhiya A, Bahn A, Burckhardt G, Wolff N: Human organic anion transporter 3 (hOAT3) can operate as an exchanger and mediate secretory urate flux. Cell Physiol Biochem. 2003;13(5):249-56. [Article]
- Tahara H, Kusuhara H, Chida M, Fuse E, Sugiyama Y: Is the monkey an appropriate animal model to examine drug-drug interactions involving renal clearance? Effect of probenecid on the renal elimination of H2 receptor antagonists. J Pharmacol Exp Ther. 2006 Mar;316(3):1187-94. Epub 2005 Nov 16. [Article]
- Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Lai Y, Sampson KE, Balogh LM, Brayman TG, Cox SR, Adams WJ, Kumar V, Stevens JC: Preclinical and clinical evidence for the collaborative transport and renal secretion of an oxazolidinone antibiotic by organic anion transporter 3 (OAT3/SLC22A8) and multidrug and toxin extrusion protein 1 (MATE1/SLC47A1). J Pharmacol Exp Ther. 2010 Sep 1;334(3):936-44. doi: 10.1124/jpet.110.170753. Epub 2010 Jun 2. [Article]
- Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
- Burt HJ, Neuhoff S, Almond L, Gaohua L, Harwood MD, Jamei M, Rostami-Hodjegan A, Tucker GT, Rowland-Yeo K: Metformin and cimetidine: Physiologically based pharmacokinetic modelling to investigate transporter mediated drug-drug interactions. Eur J Pharm Sci. 2016 Jun 10;88:70-82. doi: 10.1016/j.ejps.2016.03.020. Epub 2016 Mar 25. [Article]
- Elsby R, Chidlaw S, Outteridge S, Pickering S, Radcliffe A, Sullivan R, Jones H, Butler P: Mechanistic in vitro studies confirm that inhibition of the renal apical efflux transporter multidrug and toxin extrusion (MATE) 1, and not altered absorption, underlies the increased metformin exposure observed in clinical interactions with cimetidine, trimethoprim or pyrimethamine. Pharmacol Res Perspect. 2017 Oct;5(5). doi: 10.1002/prp2.357. [Article]
- FDA interactions table [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
- Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [Article]
- Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Zhang J, He K, Cai L, Chen YC, Yang Y, Shi Q, Woolf TF, Ge W, Guo L, Borlak J, Tong W: Inhibition of bile salt transport by drugs associated with liver injury in primary hepatocytes from human, monkey, dog, rat, and mouse. Chem Biol Interact. 2016 Aug 5;255:45-54. doi: 10.1016/j.cbi.2016.03.019. Epub 2016 Mar 19. [Article]
- Wilson A. (2016). New horizons in predictive drug metabolism and pharmacokinetics. The Royal Society of Chemistry. [ISBN:978-1-84973-828-6]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Data based on in vitro studies.
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
- Ito S, Kusuhara H, Yokochi M, Toyoshima J, Inoue K, Yuasa H, Sugiyama Y: Competitive inhibition of the luminal efflux by multidrug and toxin extrusions, but not basolateral uptake by organic cation transporter 2, is the likely mechanism underlying the pharmacokinetic drug-drug interactions caused by cimetidine in the kidney. J Pharmacol Exp Ther. 2012 Feb;340(2):393-403. doi: 10.1124/jpet.111.184986. Epub 2011 Nov 9. [Article]
- Dumitras S, Sechaud R, Drollmann A, Pal P, Vaidyanathan S, Camenisch G, Kaiser G: Effect of cimetidine, a model drug for inhibition of the organic cation transport (OCT2/MATE1) in the kidney, on the pharmacokinetics of glycopyrronium. Int J Clin Pharmacol Ther. 2013 Oct;51(10):771-9. doi: 10.5414/CP201946. [Article]
- Yonezawa A, Inui K: Importance of the multidrug and toxin extrusion MATE/SLC47A family to pharmacokinetics, pharmacodynamics/toxicodynamics and pharmacogenomics. Br J Pharmacol. 2011 Dec;164(7):1817-25. doi: 10.1111/j.1476-5381.2011.01394.x. [Article]
- FDA interactions table [Link]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55