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
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+;;
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2667937,6309467
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1444693
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
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 |
0.14 µM [Ki] | ||
Target ID: P47747 Gene ID: NA Gene Symbol: HRH2 Target Organism: Cavia porcellus (Guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9205741 |
0.19 µM [Ki] | ||
Target ID: P25021 Gene ID: 3274.0 Gene Symbol: HRH2 Target Organism: Homo sapiens (Human) Sources: http://ca.gsk.com/media/592906/zantac.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZANTAC 150 Approved UseZANTAC® (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 Date1983 |
|||
Primary | ZANTAC 150 Approved UseZANTAC® (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 Date1983 |
|||
Primary | ZANTAC 150 Approved UseZANTAC® (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 Date1983 |
|||
Primary | ZANTAC 150 Approved UseZANTAC® (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 Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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 |
T1/2
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
100 mg single, oral Highest studied dose |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | no (co-administration study) Comment: Ranitidine has no effect on midazolam exposure Sources: https://pubmed.ncbi.nlm.nih.gov/10223772/ |
|||
weak [IC50 290 uM] | ||||
weak | ||||
yes [IC50 114 uM] | ||||
yes [IC50 18.9 uM] | ||||
yes [IC50 28 uM] | ||||
yes [Ki 25 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25725698
10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:11:08 GMT 2023
by
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Record UNII |
7AJ51I17KG
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA02BA07
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NCI_THESAURUS |
C29702
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WHO-ATC |
A02BA07
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C073340
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CHEMBL1790041
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128345-62-0
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m9498
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C66505
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DD-87
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DTXSID801027716
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100000078628
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SUB15106MIG
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7AJ51I17KG
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55471
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PRIMARY | RxNorm | ||
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Ranitidine bismuth citrate
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3033887
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DBSALT001128
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ACTIVE MOIETY |
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