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 Date1995 |
||
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 |
|
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
|
Diphenhydramine prevents the haemodynamic changes of cimetidine in ICU patients. | 1991 Mar |
|
Cimetidine-dobutamine interaction? | 1992 Nov |
|
Polyuria and weight-loss associated with cimetidine. | 1992 Sep |
|
A case of cimetidine-induced acute tubulointerstitial nephritis associated with antineutrophil cytoplasmic antibody. | 1999 Feb |
|
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
|
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 |
|
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands. | 1999 Sep |
|
Cimetidine and a delayed hypersensitivity reaction. | 2000 Apr |
|
Histamine up-regulates phosphodiesterase 4 activity and reduces prostaglandin E2-inhibitory effects in human neutrophils. | 2000 Nov |
|
Increased histidine decarboxylase expression during in vitro monocyte maturation; a possible role of endogenously synthesised histamine in monocyte/macrophage differentiation. | 2001 Aug |
|
Gastroesophageal reflux in infants and children. | 2001 Dec 1 |
|
Nephrotoxicity and hepatotoxicity of histamine H2 receptor antagonists. | 2001 Jan |
|
Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer. | 2001 Jul |
|
Cimetidine-induced dystonic reaction. | 2001 Jul |
|
Prevention of vinorelbine phlebitis with cimetidine. A two-step design study. | 2001 Mar |
|
Delirium following a switch from cimetidine to famotidine. | 2001 Sep |
|
Induction of cardiac cytochrome p450 in cocaine-treated mice. | 2002 Mar |
|
Experimental anxiety induced by histaminergics in mast cell-deficient and congenitally normal mice. | 2002 May |
|
Activity of cathepsin B, D and L in rat cerebrum after cimetidine and famotidine administration. | 2003 |
|
Bioequivalence and other unresolved issues in generic drug substitution. | 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 |
|
Cimetidine-induced tubulointerstitial nephritis with both MPO-ANCA and PR3-ANCA. | 2005 Dec |
|
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 |
|
Interaction of organic cations with a newly identified plasma membrane monoamine transporter. | 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 |
|
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 |
|
[Usefulness of equations based on serum cystatin C concentration in the study of renal function]. | 2007 |
|
Cimetidine inhibits epidermal growth factor-induced cell signaling. | 2007 Mar |
|
Cimetidine induces apoptosis of human salivary gland tumor cells. | 2007 Mar |
|
Caki-1 cells as a model system for the interaction of renally secreted drugs with OCT3. | 2008 |
|
Antiulcer and anticonvulsant activity of Croton zambesicus. | 2009 Oct |
|
Novel approaches to inhibition of gastric acid secretion. | 2010 Dec |
|
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity. | 2011 Apr |
|
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
|
Record UNII |
80061L1WGD
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C29702
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
WHO-VATC |
QA02BA01
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
NDF-RT |
N0000000151
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
WHO-VATC |
QA02BA51
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
LIVERTOX |
NBK548130
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
WHO-ATC |
A02BA01
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
WHO-ATC |
A02BA51
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
||
|
NDF-RT |
N0000175784
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
335308
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
3765
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
51481-61-9
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
100000092793
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
50362
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
1134062
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
C374
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
3699
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
D002927
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
m3552
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID4020329
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
SUB06279MIG
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
CIMETIDINE
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
Cimetidine
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
2541
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | RxNorm | ||
|
3917
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
CHEMBL30
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
80061L1WGD
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
1231
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
DB00501
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
CIMETIDINE
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
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. | ||
|
2756
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
257-232-2
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
80061L1WGD
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY | |||
|
645
Created by
admin on Fri Dec 15 15:50:53 GMT 2023 , Edited by admin on Fri Dec 15 15:50:53 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TRANSPORTER -> SUBSTRATE | |||
|
TRANSPORTER -> SUBSTRATE | |||
|
BINDER->LIGAND |
BINDING
|
||
|
TRANSPORTER -> SUBSTRATE |
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> SUBSTRATE | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> SUBSTRATE |
Vmax
|
||
|
TRANSPORTER -> SUBSTRATE |
Vmax
|
||
|
METABOLIC ENZYME -> INHIBITOR |
POTENT
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> SUBSTRATE |
Km
|
||
|
TRANSPORTER -> SUBSTRATE |
Km
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> SUBSTRATE | |||
|
TARGET -> AGONIST |
IC50
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
METABOLIC ENZYME -> INHIBITOR |
POTENT
|
||
|
TARGET -> INHIBITOR |
BINDING
IC50
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
MAJOR
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||