Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H16N6S |
Molecular Weight | 252.339 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(NCCSCC1=C(C)NC=N1)=NC#N
InChI
InChIKey=AQIXAKUUQRKLND-UHFFFAOYSA-N
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB00501Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/cimetidine.html
Sources: http://www.drugbank.ca/drugs/DB00501
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/cimetidine.html
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. 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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1941 Sources: http://www.drugbank.ca/drugs/DB00501 |
70.0 nM [Ki] | ||
Target ID: CHEMBL1743126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23241029 |
1.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.drugs.com/cdi/tagamet.html |
Primary | TAGAMET Approved UseTreating and preventing ulcers of the stomach and small intestine, and treating gastroesophageal reflux disease (GERD). It may be used for treating esophagitis (inflammation of the esophagus) caused by acid reflux and certain conditions that cause increased acid secretion (eg, Zollinger-Ellison syndrome). Launch Date1995 |
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Primary | TAGAMET Approved UseTreating and preventing ulcers of the stomach and small intestine, and treating gastroesophageal reflux disease (GERD). It may be used for treating esophagitis (inflammation of the esophagus) caused by acid reflux and certain conditions that cause increased acid secretion (eg, Zollinger-Ellison syndrome). Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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1.056 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIMETIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.22 μg × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIMETIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.4 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIMETIDINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Other AEs: Headache, Abdominal pain... Other AEs: Headache (2 patients) Sources: Abdominal pain (2 patients) Nausea (2 patients) Anorexia (2 patients) Vomiting (2 patients) |
20 g single, oral Overdose |
unhealthy, adult |
|
3 g 4 times / day multiple, oral Overdose Dose: 3 g, 4 times / day Route: oral Route: multiple Dose: 3 g, 4 times / day Sources: |
unhealthy, adult |
|
300 mg 4 times / day multiple, respiratory Recommended Dose: 300 mg, 4 times / day Route: respiratory Route: multiple Dose: 300 mg, 4 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal pain | 2 patients | 1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Anorexia | 2 patients | 1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Headache | 2 patients | 1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Nausea | 2 patients | 1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Vomiting | 2 patients | 1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 50 years (range: 22-85 years) Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 110 uM] | ||||
yes [IC50 149 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/ Page: 3.0 |
yes [IC50 200 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/ Page: 4.0 |
yes [IC50 210 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/ Page: 4.0 |
yes [IC50 480 uM] | yes (co-administration study) Comment: Coadministration with midazolam: [AUC(0-12)] and AUC(0-∞) values for midazolam were 507.0 ± 265.1 (40%) and 786.1 ± 365.2 (50%) nmol/mL · h, respectively; Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/ Page: 4.0 |
||
yes [IC50 79 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ Page: 3.0 |
yes [Inhibition 10 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ Page: 5.0 |
yes [Ki 157.8 uM] | |||
yes [Ki 2.1 uM] | ||||
yes [Ki 3.8 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16278312/ Page: 3.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
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Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. | 1991 Aug 15 |
|
Cimetidine inhibits catechol estrogen metabolism in women. | 1991 Feb |
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[A case of acute interstitial nephritis and nonoliguria acute renal failure induced by cimetidine]. | 1992 Nov |
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Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
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Effects of three H2-receptor antagonists (cimetidine, famotidine, ranitidine) on serum gastrin level. | 2002 |
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Randomized trial of single agent paclitaxel given weekly versus every three weeks and with peroral versus intravenous steroid premedication to patients with ovarian cancer previously treated with platinum. | 2002 |
|
Na+/H+ exchanger blockade inhibits enterocyte inflammatory response and protects against colitis. | 2002 Jul |
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Weekly 1-h paclitaxel infusion in patients with recurrent endometrial cancer: a preliminary study. | 2003 Feb |
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Cimetidine reduces impairment of cellular immunity after transcatheter arterial embolization in patients with hepatocellular carcinoma. | 2003 Mar-Apr |
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Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). | 2004 Oct 25 |
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Cimetidine-induced tubulointerstitial nephritis with both MPO-ANCA and PR3-ANCA. | 2005 Dec |
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Sex-dependent expression and activity of the ATP-binding cassette transporter breast cancer resistance protein (BCRP/ABCG2) in liver. | 2005 May |
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Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation. | 2005 Nov |
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A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. | 2005 Oct |
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Effect of endogenous histamine in the ventral hippocampus on fear memory deficits induced by scopolamine as evaluated by step-through avoidance response in rats. | 2006 Apr 15 |
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In vitro availability of metformin in presence of h(2) receptor antagonists. | 2006 Jan |
|
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006 Jan |
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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. | 2006 Mar |
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Involvement of human multidrug and toxin extrusion 1 in the drug interaction between cimetidine and metformin in renal epithelial cells. | 2009 Apr |
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Ameliorative effects of histamine on spatial memory deficits induced by scopolamine infusion into bilateral dorsal or ventral hippocampus as evaluated by the radial arm maze task. | 2009 Aug |
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Inhibitory effects of the antiepileptic drug ethosuximide on G protein-activated inwardly rectifying K+ channels. | 2009 Feb |
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Gastroprotective activity of alkaloid extract and 2-phenylquinoline obtained from the bark of Galipea longiflora Krause (Rutaceae). | 2009 Jul 15 |
|
Pharmacokinetics of cimetidine in dogs after oral administration of cimetidine tablets. | 2009 Jun |
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Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection. | 2009 Jun |
|
The copper transporter Ctr1 contributes to cisplatin uptake by renal tubular cells during cisplatin nephrotoxicity. | 2009 Mar |
|
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity. | 2011 Apr |
|
Involvement of histaminergic receptor mechanisms in the stimulation of NT-3 synthesis in astrocytes. | 2011 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/cimetidine.html
Usual Adult Dose for Duodenal Ulcer
Parenteral: 300 mg IV or IM every 6 to 8 hours. Alternatively, a continuous IV infusion may be administered at a rate of 37.5 to 50 mg/hour, or up to a maximum rate of 100 mg/hour (2.4 g/day).
Oral: 800 mg to 1600 mg once a day at bedtime. Alternatively, dosage regimens of 300 mg four times per day, with meals and at bedtime, or 400 mg twice daily, in the morning and at bedtime, have shown to be effective.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26346531
Cimetidine (10(-7)M) inhibited IL-10 production and restored IL-12 secretion in LPS-treated murine DCs.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29702
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WHO-VATC |
QA02BA01
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NDF-RT |
N0000000151
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WHO-VATC |
QA02BA51
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LIVERTOX |
NBK548130
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WHO-ATC |
A02BA01
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A02BA51
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NDF-RT |
N0000175784
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335308
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3765
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m3552
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DTXSID4020329
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SUB06279MIG
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CIMETIDINE
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Cimetidine
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2541
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3917
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CHEMBL30
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80061L1WGD
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1231
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DB00501
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CIMETIDINE
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PRIMARY | Description: A white to off-white powder; odourless or with a faint odour.Solubility: Sparingly soluble in water; very soluble in methanol R.Category: Antiulcer drug.Storage: Cimetidine should be kept in a well-closed container. | ||
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2756
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257-232-2
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80061L1WGD
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645
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)