U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of CIMETIDINE

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)

HIDE SMILES / InChI

Description
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.

CNS Activity

Curator's Comment: Enhanced cimetidine penetration of the blood brain barrier has been demonstrated in patients with liver disease.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
70.0 nM [Ki]
1.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TAGAMET

Approved Use

Treating 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 Date

1995
Primary
TAGAMET

Approved Use

Treating 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 Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Abdominal pain (2 patients)
Nausea (2 patients)
Anorexia (2 patients)
Vomiting (2 patients)
Sources:
20 g single, oral
Overdose
Dose: 20 g
Route: oral
Route: single
Dose: 20 g
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
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
Health Status: unhealthy
Age Group: adult
Sex: M
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
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 110 uM]
yes [IC50 149 uM]
yes [IC50 200 uM]
yes [IC50 210 uM]
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;
Page: 4.0
yes [IC50 79 uM]
yes [Inhibition 10 uM]
yes [Ki 157.8 uM]
yes [Ki 2.1 uM]
yes [Ki 3.8 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
[A case of acute interstitial nephritis and nonoliguria acute renal failure induced by cimetidine].
1992 Nov
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Effects of three H2-receptor antagonists (cimetidine, famotidine, ranitidine) on serum gastrin level.
2002
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
Weekly 1-h paclitaxel infusion in patients with recurrent endometrial cancer: a preliminary study.
2003 Feb
Cimetidine reduces impairment of cellular immunity after transcatheter arterial embolization in patients with hepatocellular carcinoma.
2003 Mar-Apr
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
Sex-dependent expression and activity of the ATP-binding cassette transporter breast cancer resistance protein (BCRP/ABCG2) in liver.
2005 May
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
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
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
Inhibitory effects of the antiepileptic drug ethosuximide on G protein-activated inwardly rectifying K+ channels.
2009 Feb
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
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
Patents

Sample Use Guides

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
Cimetidine (10(-7)M) inhibited IL-10 production and restored IL-12 secretion in LPS-treated murine DCs.
Name Type Language
ACILOC
Preferred Name English
CIMETIDINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
CIMETIDINE [MI]
Common Name English
2-CYANO-1-METHYL-3-(2-(((5-METHYLIMIDAZOL-4-YL)METHYL)THIO)ETHYL)-GUANIDINE
Systematic Name English
CIMETIDINE [JAN]
Common Name English
CIMETIDINE [USAN]
Common Name English
BRUMETIDINA
Brand Name English
CIMETIDINE [IARC]
Common Name English
TAGAMET
Brand Name English
CIMAL
Brand Name English
CIMETIDINE [MART.]
Common Name English
ACINIL
Brand Name English
STOMEDINE
Brand Name English
DYSPAMET
Brand Name English
GASTROMET
Common Name English
Cimetidine [WHO-DD]
Common Name English
cimetidine [INN]
Common Name English
CIMETIDINUM [WHO-IP LATIN]
Common Name English
ULCEDIN
Brand Name English
ULCOMEDINA
Common Name English
CIMETIDINE [WHO-IP]
Common Name English
GUANIDINE, N''-CYANO-N-METHYL-N'-(2-(((5-METHYL-1H-IMIDAZOL-4-YL)METHYL)THIO)ETHYL)-
Systematic Name English
CIMETIDINE [HSDB]
Common Name English
SKF-92334
Code English
CIMETIDINE [USP-RS]
Common Name English
ULCIMET
Brand Name English
CIMETIDINE [USP MONOGRAPH]
Common Name English
CIMETIDINE [VANDF]
Common Name English
CIMETIDINE [EP MONOGRAPH]
Common Name English
CIMETIDINE [ORANGE BOOK]
Common Name English
NSC-335308
Code English
Classification Tree Code System Code
NCI_THESAURUS C29702
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
WHO-VATC QA02BA01
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
NDF-RT N0000000151
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
WHO-VATC QA02BA51
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
LIVERTOX NBK548130
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WHO-ATC A02BA01
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WHO-ATC A02BA51
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NDF-RT N0000175784
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
Code System Code Type Description
NSC
335308
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
PRIMARY
INN
3765
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PRIMARY
CAS
51481-61-9
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PRIMARY
SMS_ID
100000092793
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PRIMARY
CHEBI
50362
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PRIMARY
RS_ITEM_NUM
1134062
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PRIMARY
NCI_THESAURUS
C374
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PRIMARY
CHEBI
3699
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PRIMARY
MESH
D002927
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PRIMARY
MERCK INDEX
m3552
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PRIMARY Merck Index
EPA CompTox
DTXSID4020329
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PRIMARY
EVMPD
SUB06279MIG
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PRIMARY
WIKIPEDIA
CIMETIDINE
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PRIMARY
LACTMED
Cimetidine
Created by admin on Mon Mar 31 18:10:47 GMT 2025 , Edited by admin on Mon Mar 31 18:10:47 GMT 2025
PRIMARY
RXCUI
2541
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PRIMARY RxNorm
HSDB
3917
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PRIMARY
ChEMBL
CHEMBL30
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PRIMARY
FDA UNII
80061L1WGD
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PRIMARY
IUPHAR
1231
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PRIMARY
DRUG BANK
DB00501
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
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.
PUBCHEM
2756
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PRIMARY
ECHA (EC/EINECS)
257-232-2
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PRIMARY
DAILYMED
80061L1WGD
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PRIMARY
DRUG CENTRAL
645
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PRIMARY