U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CIMETIDINE

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)

HIDE SMILES / InChI

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

Description
Curator's Comment:: 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 nM [Ki]
1.19999999999999996 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

803433600000
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

803433600000
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
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
[Cimetidine-induced aplastic anemia complicated with nonbacterial thrombotic endocarditis and cerebral infarction].
1990 Dec
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity.
1991
Nifedipine versus cimetidine in prevention of stress-induced gastric ulcers in rats.
1991 Jan 3
Diphenhydramine prevents the haemodynamic changes of cimetidine in ICU patients.
1991 Mar
Cimetidine-dobutamine interaction?
1992 Nov
Cimetidine and a delayed hypersensitivity reaction.
2000 Apr
Nephrotoxicity and hepatotoxicity of histamine H2 receptor antagonists.
2001 Jan
Cimetidine-induced dystonic reaction.
2001 Jul
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
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
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
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
Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A).
2004 Oct 25
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
Comparative study of the speed of acid-suppressing effects of oral administration of cimetidine and famotidine.
2005 Jul
Alteration of intracellular histamine H2 receptor cycling precedes antagonist-induced upregulation.
2005 Nov
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.
2005 Oct 1
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
Cimetidine inhibits epidermal growth factor-induced cell signaling.
2007 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
Ocular surface tumors.
2009 Jan
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
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.
2010
Novel approaches to inhibition of gastric acid secretion.
2010 Dec
Bioactivation of lamotrigine in vivo in rat and in vitro in human liver microsomes, hepatocytes, and epidermal keratinocytes: characterization of thioether conjugates by liquid chromatography/mass spectrometry and high field nuclear magnetic resonance spectroscopy.
2010 Jan
Drug interaction and pharmacist.
2010 Jul
Cimetidine induces apoptosis in gastric cancer cells in vitro and inhibits tumor growth in vivo.
2010 Mar
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
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
Patents

Sample Use Guides

Usual Adult Dose for Duodenal Ulcer
Route of Administration: Other
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 Fri Jun 25 20:52:14 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:14 UTC 2021
Record UNII
80061L1WGD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CIMETIDINE [WHO-DD]
Common Name English
DYSPAMET
Brand Name English
GASTROMET
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
ACILOC
Brand 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 Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
WHO-VATC QA02BA01
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
NDF-RT N0000000151
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
WHO-VATC QA02BA51
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
LIVERTOX 209
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
WHO-ATC A02BA01
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
WHO-ATC A02BA51
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
NDF-RT N0000175784
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
Code System Code Type Description
INN
3765
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
CAS
51481-61-9
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
NCI_THESAURUS
C374
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
MESH
D002927
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
MERCK INDEX
M3552
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY Merck Index
EPA CompTox
51481-61-9
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
EVMPD
SUB06279MIG
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
WIKIPEDIA
CIMETIDINE
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
LACTMED
Cimetidine
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
RXCUI
2541
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY RxNorm
HSDB
3917
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL30
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
FDA UNII
80061L1WGD
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
IUPHAR
1231
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
DRUG BANK
DB00501
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CIMETIDINE
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
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
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
257-232-2
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
USP_CATALOG
1134062
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
645
Created by admin on Fri Jun 25 20:52:14 UTC 2021 , Edited by admin on Fri Jun 25 20:52:14 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
POTENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
POTENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
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