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Details

Stereochemistry ACHIRAL
Molecular Formula C10H16N6S
Molecular Weight 252.339
Optical Activity UNSPECIFIED
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
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

Approval Year

Targets

Targets

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

PubMed

TitleDatePubMed
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
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 hepatitis].
1992 Dec 15
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
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
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
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
Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats.
2002 Apr
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.
2002 Jul
Na+/H+ exchanger blockade inhibits enterocyte inflammatory response and protects against colitis.
2002 Jul
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
Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells.
2003
Histamine inhibits atrial myocytic ANP release via H2 receptor-cAMP-protein kinase signaling.
2003 Aug
Weekly 1-h paclitaxel infusion in patients with recurrent endometrial cancer: a preliminary study.
2003 Feb
Bioequivalence and other unresolved issues in generic drug substitution.
2003 Nov
Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.
2004 May
Different transport properties between famotidine and cimetidine by human renal organic ion transporters (SLC22A).
2004 Oct 25
Carrier-mediated uptake of H2-receptor antagonists by the rat choroid plexus: involvement of rat organic anion transporter 3.
2004 Sep
Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK).
2005 Aug
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
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice.
2005 Nov
Interaction of organic cations with a newly identified plasma membrane monoamine transporter.
2005 Nov
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
Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2.
2006 Aug
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
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
Androgen action via testicular peritubular myoid cells is essential for male fertility.
2009 Dec
Inhibitory effects of the antiepileptic drug ethosuximide on G protein-activated inwardly rectifying K+ channels.
2009 Feb
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
Novel approaches to inhibition of gastric acid secretion.
2010 Dec
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

In Vivo Use Guide
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: Parenteral or a continuous IV infusion
In Vitro Use Guide
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 Mon Oct 21 20:42:39 UTC 2019
Edited
by admin
on Mon Oct 21 20:42:39 UTC 2019
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
CIMETIDINE [EP]
Common Name English
SKF-92334
Code English
CIMETIDINE [USP-RS]
Common Name English
ULCIMET
Brand Name English
ACILOC
Brand Name English
CIMETIDINE [VANDF]
Common Name English
CIMETIDINE [ORANGE BOOK]
Common Name English
CIMETIDINE [USP]
Common Name English
NSC-335308
Code English
Classification Tree Code System Code
NCI_THESAURUS C29702
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
WHO-VATC QA02BA01
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
NDF-RT N0000000151
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
WHO-VATC QA02BA51
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
LIVERTOX 209
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
WHO-ATC A02BA01
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
WHO-ATC A02BA51
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
NDF-RT N0000175784
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
Code System Code Type Description
INN
3765
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
CAS
51481-61-9
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
NCI_THESAURUS
C374
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
MESH
D002927
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
MERCK INDEX
M3552
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY Merck Index
EPA CompTox
51481-61-9
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
EVMPD
SUB06279MIG
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
WIKIPEDIA
CIMETIDINE
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
RXCUI
2541
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY RxNorm
HSDB
51481-61-9
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL30
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
IUPHAR
1231
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
DRUG BANK
DB00501
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
LactMed
51481-61-9
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CIMETIDINE
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
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 Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
ECHA (EC/EINECS)
257-232-2
Created by admin on Mon Oct 21 20:42:39 UTC 2019 , Edited by admin on Mon Oct 21 20:42:39 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
POTENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
POTENT
TARGET -> INHIBITOR
Related Record Type Details
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