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)
Molecular Formula | C10H16N6S |
Molecular Weight | 252.339 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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 |
---|---|---|---|
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 |
---|---|---|---|---|
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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 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 n = 3 Health Status: unhealthy Age Group: adult Population Size: 3 Sources: |
|
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 n = 1 Health Status: unhealthy Condition: duodenal ulcer Age Group: adult Sex: M Population Size: 1 Sources: |
|
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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 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) n = 17 Health Status: unhealthy Age Group: 50 years (range: 22-85 years) Population Size: 17 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
Hemodynamic effects of H2-receptor antagonists. | 1990 Nov |
|
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. | 1991 Aug 15 |
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[Cimetidine hepatitis]. | 1992 Dec 15 |
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Cimetidine-dobutamine interaction? | 1992 Nov |
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Histamine and histamine-receptor antagonists modify gene expression and biosynthesis of interferon gamma in peripheral human blood mononuclear cells and in CD19-depleted cell subsets. | 1999 Nov 1 |
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Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands. | 1999 Sep |
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Gastroesophageal reflux in infants and children. | 2001 Dec 1 |
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Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer. | 2001 Jul |
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Cimetidine-induced dystonic reaction. | 2001 Jul |
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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Na+/H+ exchanger blockade inhibits enterocyte inflammatory response and protects against colitis. | 2002 Jul |
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Activity of cathepsin B, D and L in rat cerebrum after cimetidine and famotidine administration. | 2003 |
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[Roles of histamine receptors in pain perception: a study using receptors gene knockout mice]. | 2003 Nov |
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Regulation of cytokine production in carcinoembryonic antigen stimulated Kupffer cells by beta-2 adrenergic receptors: implications for hepatic metastasis. | 2004 Jun 25 |
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Metabolism of territrem B and C in liver microsomes from 14-wk-old Wistar rats is catalyzed by cytochrome P-450 3A. | 2005 Feb 27 |
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Comparative study of the speed of acid-suppressing effects of oral administration of cimetidine and famotidine. | 2005 Jul |
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Feasibility of biowaiver extension to biopharmaceutics classification system class III drug products: cimetidine. | 2006 |
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In vitro availability of metformin in presence of h(2) receptor antagonists. | 2006 Jan |
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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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Effects of histamine 2 receptor antagonists on endothelial-neutrophil adhesion and surface expression of endothelial adhesion molecules induced by high glucose levels. | 2007 Jan-Feb |
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Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. | 2007 Jul 15 |
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Cimetidine inhibits epidermal growth factor-induced cell signaling. | 2007 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 |
|
Ocular surface tumors. | 2009 Jan |
|
Immune hemolytic anemia due to cimetidine: the first example of a cimetidine antibody. | 2010 Feb |
|
Size-dependent effects of nanoparticles on the activity of cytochrome P450 isoenzymes. | 2010 Feb 1 |
|
Contribution of mast cells to the oedema induced by Bothrops moojeni snake venom and a pharmacological assessment of the inflammatory mediators involved. | 2010 Feb-Mar |
|
OCT1 Expression in adipocytes could contribute to increased metformin action in obese subjects. | 2011 Jan |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:50:53 GMT 2023
by
admin
on
Fri Dec 15 15:50:53 GMT 2023
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Record UNII |
80061L1WGD
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Record Status |
Validated (UNII)
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Record Version |
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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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WHO-ATC |
A02BA51
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NDF-RT |
N0000175784
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3765
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1134062
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C374
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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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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE |
Vmax
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TRANSPORTER -> SUBSTRATE |
Vmax
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METABOLIC ENZYME -> INHIBITOR |
POTENT
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE |
Km
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TRANSPORTER -> SUBSTRATE |
Km
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TARGET -> AGONIST |
IC50
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
POTENT
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TARGET -> INHIBITOR |
BINDING
IC50
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
URINE
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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