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 |
|
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 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 |
---|---|---|---|
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 |
---|---|---|
[Cimetidine-induced aplastic anemia complicated with nonbacterial thrombotic endocarditis and cerebral infarction]. | 1990 Dec |
|
[Confusion induced by the combination cimetidine-benzodiazepine; apropos of a case report]. | 1990 Jan |
|
Hemodynamic effects of H2-receptor antagonists. | 1990 Nov |
|
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
|
Cimetidine inhibits catechol estrogen metabolism in women. | 1991 Feb |
|
Diphenhydramine prevents the haemodynamic changes of cimetidine in ICU patients. | 1991 Mar |
|
[Cimetidine hepatitis]. | 1992 Dec 15 |
|
[A case of acute interstitial nephritis and nonoliguria acute renal failure induced by cimetidine]. | 1992 Nov |
|
Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation. | 2001 Aug |
|
Nephrotoxicity and hepatotoxicity of histamine H2 receptor antagonists. | 2001 Jan |
|
Prevention of vinorelbine phlebitis with cimetidine. A two-step design study. | 2001 Mar |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. | 2002 Jul |
|
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 |
|
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 |
|
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 |
|
Sex-dependent expression and activity of the ATP-binding cassette transporter breast cancer resistance protein (BCRP/ABCG2) in liver. | 2005 May |
|
Feasibility of biowaiver extension to biopharmaceutics classification system class III drug products: cimetidine. | 2006 |
|
Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2. | 2006 Aug |
|
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 |
|
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 |
|
Involvement of human multidrug and toxin extrusion 1 in the drug interaction between cimetidine and metformin in renal epithelial cells. | 2009 Apr |
|
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 |
|
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 |
|
Pharmacokinetics of cimetidine in dogs after oral administration of cimetidine tablets. | 2009 Jun |
|
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 |
|
Enhanced ERbeta immunoexpression and apoptosis in the germ cells of cimetidine-treated rats. | 2009 Nov 18 |
|
Antiulcer and anticonvulsant activity of Croton zambesicus. | 2009 Oct |
|
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 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:19:15 UTC 2023
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on
Wed Jul 05 23:19:15 UTC 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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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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335308
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3765
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51481-61-9
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100000092793
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50362
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1134062
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C374
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3699
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D002927
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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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TRANSPORTER -> SUBSTRATE | |||
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BINDING
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POTENT
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METABOLIC ENZYME -> INHIBITOR |
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METABOLITE -> PARENT | |||
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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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