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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16N6S
Molecular Weight 252.339
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

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

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)
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)
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
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
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)
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

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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:53 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:53 GMT 2023
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
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
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 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
NSC
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
INN
3765
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PRIMARY
CAS
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
SMS_ID
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
CHEBI
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
RS_ITEM_NUM
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
NCI_THESAURUS
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
CHEBI
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
MESH
D002927
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PRIMARY
MERCK INDEX
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
EPA CompTox
DTXSID4020329
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PRIMARY
EVMPD
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
WIKIPEDIA
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
LACTMED
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
RXCUI
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
HSDB
3917
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PRIMARY
ChEMBL
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
FDA UNII
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
IUPHAR
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
DRUG BANK
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
WHO INTERNATIONAL PHARMACOPEIA
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.
PUBCHEM
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
ECHA (EC/EINECS)
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
DAILYMED
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
DRUG CENTRAL
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
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC