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Details

Stereochemistry ACHIRAL
Molecular Formula C13H22N4O3S.C6H5O7.Bi
Molecular Weight 712.484
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RANITIDINE BISMUTH CITRATE

SMILES

[Bi+3].OC(CC([O-])=O)(CC([O-])=O)C([O-])=O.CNC(NCCSCC1=CC=C(CN(C)C)O1)=C[N+]([O-])=O

InChI

InChIKey=XAUTYMZTJWXZHZ-IGUOPLJTSA-K
InChI=1S/C13H22N4O3S.C6H8O7.Bi/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3;7-3(8)1-6(13,5(11)12)2-4(9)10;/h4-5,9,14-15H,6-8,10H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);/q;;+3/p-3/b13-9+;;

HIDE SMILES / InChI

Molecular Formula C6H5O7
Molecular Weight 189.0997
Charge -3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Bi
Molecular Weight 208.9804
Charge 3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H22N4O3S
Molecular Weight 314.404
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Ranitidine, a histamine H2-receptor antagonist, is now well established as a potent inhibitor of gastric acid secretion effective in the treatment and prophylaxis of gastrointestinal lesions aggravated by gastric acid secretion.

CNS Activity

Curator's Comment: Ranitidine, when given in conventional doses, can cause adverse central nervous system reactions (CNS-ADRs), particularly in older patients who have substantial renal function impairment. These CNS-ADRs occur as a consequence of altered ranitidine disposition. Ranitidine doses should be reduced when renal function impairment is present, and patients should be carefully observed for CNS-ADRs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P25102
Gene ID: 25461.0
Gene Symbol: Hrh2
Target Organism: Rattus norvegicus (Rat)
0.14 µM [Ki]
Target ID: P47747
Gene ID: NA
Gene Symbol: HRH2
Target Organism: Cavia porcellus (Guinea pig)
0.19 µM [Ki]
Target ID: P25021
Gene ID: 3274.0
Gene Symbol: HRH2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZANTAC 150

Approved Use

ZANTAC® (ranitidine hydrochloride) Tablets and Injection are indicated for the treatment of duodenal ulcer, benign gastric ulcer, reflux esophagitis, post-operative peptic ulcer, Zollinger-Ellison Syndrome, and other conditions where reduction of gastric secretion and acid output is desirable. These include the following: • the treatment of nonsteroidal anti-inflammatory drug (NSAID)- induced lesions, both ulcers and erosions, and their gastrointestinal (GI) symptoms and the prevention of their recurrence; • the prophylaxis of GI hemorrhage from stress ulceration in seriously ill patients; • the prophylaxis of recurrent hemorrhage from bleeding ulcers; • the prevention of Acid Aspiration Syndrome from general anaesthesia in patients considered to be at risk for this, including obstetrical patients in labour, and obese patients. In addition, ZANTAC® is indicated for the prophylaxis and maintenance treatment of duodenal or benign gastric ulcer in patients with a history of recurrent ulceration.

Launch Date

1983
Primary
ZANTAC 150

Approved Use

ZANTAC® (ranitidine hydrochloride) Tablets and Injection are indicated for the treatment of duodenal ulcer, benign gastric ulcer, reflux esophagitis, post-operative peptic ulcer, Zollinger-Ellison Syndrome, and other conditions where reduction of gastric secretion and acid output is desirable. These include the following: • the treatment of nonsteroidal anti-inflammatory drug (NSAID)- induced lesions, both ulcers and erosions, and their gastrointestinal (GI) symptoms and the prevention of their recurrence; • the prophylaxis of GI hemorrhage from stress ulceration in seriously ill patients; • the prophylaxis of recurrent hemorrhage from bleeding ulcers; • the prevention of Acid Aspiration Syndrome from general anaesthesia in patients considered to be at risk for this, including obstetrical patients in labour, and obese patients. In addition, ZANTAC® is indicated for the prophylaxis and maintenance treatment of duodenal or benign gastric ulcer in patients with a history of recurrent ulceration.

Launch Date

1983
Primary
ZANTAC 150

Approved Use

ZANTAC® (ranitidine hydrochloride) Tablets and Injection are indicated for the treatment of duodenal ulcer, benign gastric ulcer, reflux esophagitis, post-operative peptic ulcer, Zollinger-Ellison Syndrome, and other conditions where reduction of gastric secretion and acid output is desirable. These include the following: • the treatment of nonsteroidal anti-inflammatory drug (NSAID)- induced lesions, both ulcers and erosions, and their gastrointestinal (GI) symptoms and the prevention of their recurrence; • the prophylaxis of GI hemorrhage from stress ulceration in seriously ill patients; • the prophylaxis of recurrent hemorrhage from bleeding ulcers; • the prevention of Acid Aspiration Syndrome from general anaesthesia in patients considered to be at risk for this, including obstetrical patients in labour, and obese patients. In addition, ZANTAC® is indicated for the prophylaxis and maintenance treatment of duodenal or benign gastric ulcer in patients with a history of recurrent ulceration.

Launch Date

1983
Primary
ZANTAC 150

Approved Use

ZANTAC® (ranitidine hydrochloride) Tablets and Injection are indicated for the treatment of duodenal ulcer, benign gastric ulcer, reflux esophagitis, post-operative peptic ulcer, Zollinger-Ellison Syndrome, and other conditions where reduction of gastric secretion and acid output is desirable. These include the following: • the treatment of nonsteroidal anti-inflammatory drug (NSAID)- induced lesions, both ulcers and erosions, and their gastrointestinal (GI) symptoms and the prevention of their recurrence; • the prophylaxis of GI hemorrhage from stress ulceration in seriously ill patients; • the prophylaxis of recurrent hemorrhage from bleeding ulcers; • the prevention of Acid Aspiration Syndrome from general anaesthesia in patients considered to be at risk for this, including obstetrical patients in labour, and obese patients. In addition, ZANTAC® is indicated for the prophylaxis and maintenance treatment of duodenal or benign gastric ulcer in patients with a history of recurrent ulceration.

Launch Date

1983
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
440 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RANITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
948.6 ng × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RANITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.69 h
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RANITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.5 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RANITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RANITIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, adult
n = 136
Health Status: healthy
Age Group: adult
Sex: M+F
Population Size: 136
Sources:
1500 mg single, oral
Overdose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, children
n = 517
Health Status: unknown
Age Group: children
Sex: unknown
Population Size: 517
Sources:
Overview

Overview

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Histamine H2 antagonists and the nervous system.
1985 Dec
Comparison of ranitidine and high-dose antacid in the treatment of prepyloric or duodenal ulcer. A double-blind controlled trial.
1985 Jan
Bradycardia and neurologic disorders associated with ranitidine in a child.
1985 May
Mental confusion as a side effect of ranitidine.
1986 Feb
Depression associated with ranitidine.
1986 Jul
Histamine and hepatic glutathione in the mouse.
1987 May 25
Fatal renal and hepatic toxicity after treatment with diltiazem.
1987 Nov 14
Cardiac arrest associated with ranitidine.
1989 Aug 19
Mechanism of ranitidine associated anemia.
1989 Jun
Seizures during concomitant treatment with theophylline and ranitidine: a case report.
1990 Oct-Dec
Ranitidine-associated delirium.
1990 Winter
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity.
1991
Ranitidine and depression.
1991 Sep
Ranitidine does not alter adinazolam pharmacokinetics or pharmacodynamics.
1992 Aug
Ranitidine pharmacokinetics and adverse central nervous system reactions.
1992 Nov
Clarithromycin-induced acute psychoses in peptic ulcer disease.
1999 Jan
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
[Aseptic meningitis after ranitidine treatment for systemic lupus erythematosus].
1999 Nov 13
Ranitidine-related Stevens-Johnson syndrome in patients with severe liver diseases: a report of two cases.
2001 Apr
Ranitidine-induced acute interstitial nephritis in a cadaveric renal allograft.
2001 Jul
Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer.
2001 Jul
Control of intragastric acidity with over-the-counter doses of ranitidine or famotidine.
2001 Oct
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats.
2002 Apr
Histamine regulation of interleukin-18-initiating cytokine cascade is associated with down-regulation of intercellular adhesion molecule-1 expression in human peripheral blood mononuclear cells.
2002 Jan
Are proton pump inhibitors the first choice for acute treatment of gastric ulcers? A meta analysis of randomized clinical trials.
2002 Jul 15
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Ranitidine reduces ischemia/reperfusion-induced liver injury in rats by inhibiting neutrophil activation.
2002 Jun
Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells.
2003
Radioprotective properties of histamine H2 receptor antagonists: present and future prospects.
2003 Jun
Ranitidine treatment during a modest inflammatory response precipitates idiosyncrasy-like liver injury in rats.
2003 Oct
Intrahepatic cholestatic jaundice related to administration of ranitidine. A case report with histologic and ultramicroscopic study.
2004 Dec
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Carrier-mediated uptake of H2-receptor antagonists by the rat choroid plexus: involvement of rat organic anion transporter 3.
2004 Sep
Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects.
2005
Role of histamine in airway remodeling of asthmatic guinea pig.
2005 Dec 25
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of ranitidine.
2005 Jan-Feb
Laryngopharyngeal reflux: prospective cohort study evaluating optimal dose of proton-pump inhibitor therapy and pretherapy predictors of response.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters.
2005 Oct
Unique gene expression and hepatocellular injury in the lipopolysaccharide-ranitidine drug idiosyncrasy rat model: comparison with famotidine.
2006 Apr
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes.
2006 Aug
Attenuation of indomethacin- and HCl/ethanol-induced oxidative gastric mucosa damage in rats by kolaviron, a natural biflavonoid of Garcinia kola seed.
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
Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine.
2006 May
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.
2007 Nov
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.
2007 Sep
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.
2011 Feb
The mediation of the central histaminergic system in the pressor effect of intracerebroventricularly injected melittin, a phospholipase A2 activator, in normotensive rats.
2012 Oct-Nov
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In some hospitalized patients with pathological hypersecretory conditions or intractable duodenal ulcers, or in patients unable to take oral medication, ZANTAC® may be administered parenterally (intramuscular or intravenous injections): 50 mg (2 mL) every six to eight hours.
150 mg twice daily (tablets or syrup)
Route of Administration: Oral
10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:08 GMT 2023
Record UNII
7AJ51I17KG
Record Status Validated (UNII)
Record Version
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Name Type Language
RANITIDINE BISMUTH CITRATE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
RANITIDINE BISMUTH CITRATE [VANDF]
Common Name English
1,2,3-PROPANETRICARBOXYLIC ACID, 2-HYDROXY-, BISMUTH(3+) SALT, COMPD. WITH N-(2-(((5-((DIMETHYLAMINO)METHYL)-2-FURANYL)METHYL)THIO)ETHYL)-N'-METHYL-2-NITRO-1,1-ETHENEDIAMINE (1:1:1)
Common Name English
GR-122311X
Code English
RANITIDINE BISMUTH CITRATE [USAN]
Common Name English
RANITIDINE BISMUTH CITRATE [ORANGE BOOK]
Common Name English
GR 122311X
Code English
Ranitidine bismuth citrate [WHO-DD]
Common Name English
TRITEC
Brand Name English
RANITIDINE BISMUTH CITRATE [MI]
Common Name English
RANITIDINE BISMUTH CITRATE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QA02BA07
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
NCI_THESAURUS C29702
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
WHO-ATC A02BA07
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
Code System Code Type Description
MESH
C073340
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL1790041
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
CAS
128345-62-0
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
MERCK INDEX
m9498
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C66505
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
USAN
DD-87
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID801027716
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
SMS_ID
100000078628
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
EVMPD
SUB15106MIG
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
FDA UNII
7AJ51I17KG
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
RXCUI
55471
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
Ranitidine bismuth citrate
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
PUBCHEM
3033887
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
DRUG BANK
DBSALT001128
Created by admin on Fri Dec 15 16:11:08 GMT 2023 , Edited by admin on Fri Dec 15 16:11:08 GMT 2023
PRIMARY
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ACTIVE MOIETY