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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H22N4O3S.C6H5O7.Bi
Molecular Weight 712.4857
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RANITIDINE BISMUTH CITRATE

SMILES

CN/C(=C(/[H])\N(=O)=O)/NCCSCc1ccc(CN(C)C)o1.C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])O.[Bi+3]

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 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 314.4054
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H5O7
Molecular Weight 189.1
Charge -3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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

4.23964803E11
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

4.23964803E11
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

4.23964803E11
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

4.23964803E11
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
Bradycardia and neurologic disorders associated with ranitidine in a child.
1985 May
Mania associated with intravenous ranitidine therapy.
1987 Nov
Famotidine-associated mental confusion in elderly patients.
1988 Dec
First-degree atrioventricular block in a young duodenal ulcer patient treated with a standard oral dose of ranitidine.
1988 Jul
Ranitidine and bradycardia.
1988 Mar
Ranitidine-induced confusion with concomitant morphine.
1988 Nov
Cardiac arrest associated with ranitidine.
1989 Aug 19
Famotidine and ranitidine, but not cimetidine, cause severe, disabling headache.
1989 Feb
Mechanism of ranitidine associated anemia.
1989 Jun
Ranitidine does not alter adinazolam pharmacokinetics or pharmacodynamics.
1992 Aug
Ranitidine-induced acute dystonia.
1999 May
Depression or hypoactive delirium? A report of ciprofloxacin-induced mental disorder in a patient with chronic obstructive pulmonary disease.
2001 Jan-Feb
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Drug points: Severe myalgia from an interaction between treatments with pantoprazole and methotrexate.
2002 Jun 22
Ranitidine treatment during a modest inflammatory response precipitates idiosyncrasy-like liver injury in rats.
2003 Oct
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects.
2005
Drug specificity and intestinal membrane localization of human organic cation transporters (OCT).
2005 Dec 5
Laryngopharyngeal reflux: prospective cohort study evaluating optimal dose of proton-pump inhibitor therapy and pretherapy predictors of response.
2005 Jul
Mechanisms of action of leptin in preventing gastric ulcer.
2005 Jul 21
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Inlet patch of gastric mucosa in upper esophagus causing chronic cough and vocal cord dysfunction.
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
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.
2007 Sep
Protective effect of histamine H2 receptor antagonist ranitidine against rotenone-induced apoptosis.
2009 Nov
Discovery of two clinical histamine H(3) receptor antagonists: trans-N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidinylmethyl)phenyl]cyclobutanecarboxamide (PF-03654746) and trans-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-N-(2-methylpropyl)cyclobutanecarboxamide (PF-03654764).
2011 Nov 10
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
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 Jun 25 20:44:22 UTC 2021
Edited
by admin
on Fri Jun 25 20:44:22 UTC 2021
Record UNII
7AJ51I17KG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RANITIDINE BISMUTH CITRATE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
RANITIDINE BISMUTH CITRATE [WHO-DD]
Common 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
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 Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
NCI_THESAURUS C29702
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
WHO-ATC A02BA07
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
Code System Code Type Description
MESH
C073340
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL1790041
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
CAS
128345-62-0
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
MERCK INDEX
M9498
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C66505
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
EVMPD
SUB15106MIG
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
FDA UNII
7AJ51I17KG
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
RXCUI
55471
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY RxNorm
PUBCHEM
3033887
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
DRUG BANK
DBSALT001128
Created by admin on Fri Jun 25 20:44:22 UTC 2021 , Edited by admin on Fri Jun 25 20:44:22 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY