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
Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia.
1991 Aug 15
[Cimetidine hepatitis].
1992 Dec 15
Cimetidine-dobutamine interaction?
1992 Nov
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
Gastroesophageal reflux in infants and children.
2001 Dec 1
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
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Na+/H+ exchanger blockade inhibits enterocyte inflammatory response and protects against colitis.
2002 Jul
Activity of cathepsin B, D and L in rat cerebrum after cimetidine and famotidine administration.
2003
[Roles of histamine receptors in pain perception: a study using receptors gene knockout mice].
2003 Nov
Regulation of cytokine production in carcinoembryonic antigen stimulated Kupffer cells by beta-2 adrenergic receptors: implications for hepatic metastasis.
2004 Jun 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
Feasibility of biowaiver extension to biopharmaceutics classification system class III drug products: cimetidine.
2006
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
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
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
2007 Jul 15
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
Ocular surface tumors.
2009 Jan
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
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
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
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
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
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