Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H16N6S |
Molecular Weight | 252.3407 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1c(CSCCNC(=NC)NC#N)[nH]cn1
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 | 252.3407 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
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 Date8.0343361E11 |
||
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 Date8.0343361E11 |
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 |
---|---|---|---|
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 |
|
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
|
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 |
|
[Cimetidine hepatitis]. | 1992 Dec 15 |
|
Cimetidine-dobutamine interaction? | 1992 Nov |
|
Polyuria and weight-loss associated with cimetidine. | 1992 Sep |
|
Activity of cathepsin B, D and L in rat cerebrum after cimetidine and famotidine administration. | 2003 |
|
Radioprotective properties of histamine H2 receptor antagonists: present and future prospects. | 2003 Jun |
|
Bioequivalence and other unresolved issues in generic drug substitution. | 2003 Nov |
|
[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 |
|
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004 May |
|
Relative contribution of OAT and OCT transporters to organic electrolyte transport in rabbit proximal tubule. | 2004 Nov |
|
Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A). | 2004 Oct 25 |
|
Carrier-mediated uptake of H2-receptor antagonists by the rat choroid plexus: involvement of rat organic anion transporter 3. | 2004 Sep |
|
Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK). | 2005 Aug |
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Cimetidine-induced tubulointerstitial nephritis with both MPO-ANCA and PR3-ANCA. | 2005 Dec |
|
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 |
|
Human breast cancer resistance protein: interactions with steroid drugs, hormones, the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine, and transport of cimetidine. | 2005 Jan |
|
Comparative study of the speed of acid-suppressing effects of oral administration of cimetidine and famotidine. | 2005 Jul |
|
Sex-dependent expression and activity of the ATP-binding cassette transporter breast cancer resistance protein (BCRP/ABCG2) in liver. | 2005 May |
|
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice. | 2005 Nov |
|
Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation. | 2005 Nov |
|
A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. | 2005 Oct |
|
Feasibility of biowaiver extension to biopharmaceutics classification system class III drug products: cimetidine. | 2006 |
|
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 |
|
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. | 2006 Aug |
|
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 |
|
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 |
|
Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney. | 2006 Nov |
|
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 |
|
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. | 2007 Jul 15 |
|
Cimetidine induces apoptosis of human salivary gland tumor cells. | 2007 Mar |
|
Involvement of human multidrug and toxin extrusion 1 in the drug interaction between cimetidine and metformin in renal epithelial cells. | 2009 Apr |
|
Androgen action via testicular peritubular myoid cells is essential for male fertility. | 2009 Dec |
|
Visions of drug discovery. Cimetidine (Tagamet). | 2009 Feb |
|
Ocular surface tumors. | 2009 Jan |
|
Gastroprotective activity of alkaloid extract and 2-phenylquinoline obtained from the bark of Galipea longiflora Krause (Rutaceae). | 2009 Jul 15 |
|
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection. | 2009 Jun |
|
Antiulcer and anticonvulsant activity of Croton zambesicus. | 2009 Oct |
|
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 |
|
Drug interaction and pharmacist. | 2010 Jul |
|
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity. | 2011 Apr |
|
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists. | 2011 Feb |
|
OCT1 Expression in adipocytes could contribute to increased metformin action in obese subjects. | 2011 Jan |
|
Gastroprotective mechanisms of Citrus lemon (Rutaceae) essential oil and its majority compounds limonene and β-pinene: involvement of heat-shock protein-70, vasoactive intestinal peptide, glutathione, sulfhydryl compounds, nitric oxide and prostaglandin E₂. | 2011 Jan 15 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:52:14 UTC 2021
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admin
on
Fri Jun 25 20:52:14 UTC 2021
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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
Created by
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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 |
209
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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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Code System | Code | Type | Description | ||
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3765
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51481-61-9
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PRIMARY | |||
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C374
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D002927
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M3552
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PRIMARY | Merck Index | ||
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51481-61-9
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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
Created by
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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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1134062
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PRIMARY | USP-RS | ||
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645
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
POTENT
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TRANSPORTER -> INHIBITOR | |||
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ACTIVE MOIETY |
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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