RANITIDINE BISMUTH CITRATE

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 Search

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	C13H22N4O3S
Molecular Weight	314.404
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2667937,6309467

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H2 receptor 46 Target ID: P25102 Gene ID: 25461.0 Gene Symbol: Hrh2 Target Organism: Rattus norvegicus (Rat) Sources: http://www.pnas.org/content/93/13/6802.full.pdf	Antagonist 2849	0.14 µM [Ki]
Histamine H2 receptor 46 Target ID: P47747 Gene ID: NA Gene Symbol: HRH2 Target Organism: Cavia porcellus (Guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9205741	Antagonist 2849	0.19 µM [Ki]
Histamine H2 receptor 46 Target ID: P25021 Gene ID: 3274.0 Gene Symbol: HRH2 Target Organism: Homo sapiens (Human) Sources: http://ca.gsk.com/media/592906/zantac.pdf	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 49 Sources: http://ca.gsk.com/media/592906/zantac.pdf	Primary	Approved 8583	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
Gastric ulcer 74 Sources: http://ca.gsk.com/media/592906/zantac.pdf	Primary	Approved 8583	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
Gastroesophageal reflux disease 68 Sources: http://ca.gsk.com/media/592906/zantac.pdf	Primary	Approved 8583	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
Zollinger-Ellison syndrome 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018703s065,019675s031,020251s016lbl.pdf	Primary	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
440 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018703s068,019675s035,020251s019lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
948.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6094785/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6094785/	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018703s068,019675s035,020251s019lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018703s068,019675s035,020251s019lbl.pdf	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

Dose	Population	Adverse events
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6329583/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6329583/	Sources: https://pubmed.ncbi.nlm.nih.gov/6329583/
1500 mg single, oral Overdose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/28425352/	unknown, children Health Status: unknown Age Group: children Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/28425352/	Sources: https://pubmed.ncbi.nlm.nih.gov/28425352/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946		inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 OCT2 779 OCT3 159 MATE1 415 MATE2 267 CYP3A 227 CYP1A2 2153	OCT1 393 OCT2 434 OCT3 92 P-gp 2052 FMO3 77 FMO1 25 CYP1A2 1197 CYP2A6 626 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/	no
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/	no	no (co-administration study) Comment: Ranitidine has no effect on midazolam exposure Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/
OCT3 161	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	weak [IC50 290 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.fda.gov/drugs/drug-interactions-labeling/drug-development-and-drug-interactions-table-substrates-inhibitors-and-inducers	weak
OCT2 782	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	yes [IC50 114 uM]
MATE1 416	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20053795	yes [IC50 18.9 uM]
OCT1 656	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	yes [IC50 28 uM]
MATE2 267	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 25 uM]

Drug as victim

Target	Modality	Activity
FMO3 77	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	major
FMO1 25	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	minor
OCT2 434	substrate 4014 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	no
OCT3 92	substrate 4014 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11128045/	yes
OCT1 393	substrate 4014 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16141367	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9862768/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8776	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8776
ChemicalBook	CB5480252	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5480252
MolPort	MolPort-003-666-370	https://www.molport.com/shop/molecule-link/MolPort-003-666-370
ZINC	ZINC000001530728	http://zinc15.docking.org/substances/ZINC000001530728

PubMed

Title	Date	PubMed
Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds.	2014-12-05	25451594
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.	2014-01	24085192
The mediation of the central histaminergic system in the pressor effect of intracerebroventricularly injected melittin, a phospholipase A2 activator, in normotensive rats.	2012-05-03	22995146
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).	2011-11-10	21928839
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity.	2011-04	21461253
Attenuation of stress-induced gastric lesions by lansoprazole, PD-136450 and ranitidine in rats.	2011-03	21116686
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.	2011-02	20070855
Drug-induced aseptic meningitis, sensorineural hearing loss and vestibulopaty.	2010-09	20977110
Protective effect of histamine H2 receptor antagonist ranitidine against rotenone-induced apoptosis.	2009-11	19723537
Synergistic drug-cytokine induction of hepatocellular death as an in vitro approach for the study of inflammation-associated idiosyncratic drug hepatotoxicity.	2009-06-15	19362101
Severe hypomagnesaemia due to lansoprazole.	2009	22180759
Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats.	2008	18726076
Gastroprotective and antioxidant effects of amiodarone on indomethacin-induced gastric ulcers in rats.	2007-11	18087811
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.	2007-11	17698507
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.	2007-09	17895592
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.	2007-07-15	17603938
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes.	2006-08	16723495
Coagulation-dependent gene expression and liver injury in rats given lipopolysaccharide with ranitidine but not with famotidine.	2006-05	16401727
Unique gene expression and hepatocellular injury in the lipopolysaccharide-ranitidine drug idiosyncrasy rat model: comparison with famotidine.	2006-04	16415329
In vitro availability of metformin in presence of h(2) receptor antagonists.	2006-01	16632449
Inlet patch of gastric mucosa in upper esophagus causing chronic cough and vocal cord dysfunction.	2006-01	16440542
Antisecretory and antiulcer activity of Asparagus racemosus Willd. against indomethacin plus phyloric ligation-induced gastric ulcer in rats.	2006	17135157
Switching of H(2)-Receptor Antagonists to Over-the-Counter Status in Finland : Implications for Consumption and Adverse Effects.	2005	17523774
Ranitidine and depression.	1991-09	1958166
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity.	1991	1676005
Seizures during concomitant treatment with theophylline and ranitidine: a case report.	1990-10-01	2093363
Effects of histamine H2-receptor blockade on the cardiovascular reflex response to lower-body negative pressure in man.	1990-05	1972605
Effect of ranitidine on acetaminophen-induced hepatotoxicity in dogs.	1990-03	2307085
Ranitidine-associated delirium.	1990	2300661
Cardiac arrest associated with ranitidine.	1989-08-19	2507055
Mechanism of ranitidine associated anemia.	1989-06	2735342
Ranitidine-induced chest pain.	1989-03	2718500
Histamine release in the isolated vascularly perfused stomach of the rat: regulation by autoreceptors.	1989-03	2470453
A dog model for acetaminophen-induced fulminant hepatic failure.	1989-02	2910762
Famotidine and ranitidine, but not cimetidine, cause severe, disabling headache.	1989-02	2563629
Famotidine-associated mental confusion in elderly patients.	1988-12	3243179
Ranitidine-induced confusion with concomitant morphine.	1988-11	3234261
Reversible chorea due to ranitidine and cimetidine.	1988-07-16	2899203
First-degree atrioventricular block in a young duodenal ulcer patient treated with a standard oral dose of ranitidine.	1988-07	3177090
Ranitidine and bradycardia.	1988-03	3341694
Mania-like episodes associated with ranitidine.	1988-02	3341479
Fatal renal and hepatic toxicity after treatment with diltiazem.	1987-11-14	3120959
Mania associated with intravenous ranitidine therapy.	1987-11	3500517
Myofascial headache. Exacerbation of symptoms due to diflunisal and ranitidine therapy. A case report.	1987-08	3308026
Histamine and hepatic glutathione in the mouse.	1987-05-25	2884542
Depression associated with ranitidine.	1986-07	3717435
Mental confusion as a side effect of ranitidine.	1986-02	3946668
Histamine H2 antagonists and the nervous system.	1985-12	4072863
Bradycardia and neurologic disorders associated with ranitidine in a child.	1985-05	3984961
Comparison of ranitidine and high-dose antacid in the treatment of prepyloric or duodenal ulcer. A double-blind controlled trial.	1985-01	3887547

Patents

Sample Use Guides

In Vivo Use Guide

150 mg twice daily (tablets or syrup)

Route of Administration: Oral

In Vitro Use Guide

10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:08 GMT 2025`
Record UNII	7AJ51I17KG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RANITIDINE BISMUTH CITRATE

Official Name

English

TRITEC

Preferred 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

RANITIDINE BISMUTH CITRATE [MI]

Common Name

English

RANITIDINE BISMUTH CITRATE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA02BA07