Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H22N4O3S.ClH |
Molecular Weight | 350.865 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNC(NCCSCC1=CC=C(CN(C)C)O1)=C[N+]([O-])=O
InChI
InChIKey=GGWBHVILAJZWKJ-UHFFFAOYSA-N
InChI=1S/C13H22N4O3S.ClH/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3;/h4-5,9,14-15H,6-8,10H2,1-3H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
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 |
|
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 |
|
Famotidine-associated mental confusion in elderly patients. | 1988 Dec |
|
Ranitidine and bradycardia. | 1988 Mar |
|
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-induced chest pain. | 1989 Mar |
|
Effects of histamine H2-receptor blockade on the cardiovascular reflex response to lower-body negative pressure in man. | 1990 May |
|
Ranitidine-associated delirium. | 1990 Winter |
|
Effects of antihistaminics on locomotor activity in mice. Comparison with opiate and amphetamine-induced hyperactivity. | 1991 |
|
Histamine release and SOD, allopurinol and ranitidine pretreatment in haemorrhagic shock in the rat. | 1992 |
|
Ranitidine pharmacokinetics and adverse central nervous system reactions. | 1992 Nov |
|
Effects of three H2-receptor antagonists (cimetidine, famotidine, ranitidine) on serum gastrin level. | 2002 |
|
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery. | 2002 Aug |
|
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 |
|
Drug points: Severe myalgia from an interaction between treatments with pantoprazole and methotrexate. | 2002 Jun 22 |
|
Effects of histamine H(2)-receptor antagonists on human plasma levels of calcitonin gene-related peptide, substance P and vasoactive intestinal peptide. | 2002 Nov |
|
Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells. | 2003 |
|
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner. | 2003 Feb |
|
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 |
|
Histamine H2-receptor antagonist ranitidine protects against neural death induced by oxygen-glucose deprivation. | 2004 Oct |
|
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 |
|
Differential substrate and inhibitory activities of ranitidine and famotidine toward human organic cation transporter 1 (hOCT1; SLC22A1), hOCT2 (SLC22A2), and hOCT3 (SLC22A3). | 2005 Dec |
|
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of ranitidine. | 2005 Jan-Feb |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
|
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 |
|
Inlet patch of gastric mucosa in upper esophagus causing chronic cough and vocal cord dysfunction. | 2006 Jan |
|
Attenuation of indomethacin- and HCl/ethanol-induced oxidative gastric mucosa damage in rats by kolaviron, a natural biflavonoid of Garcinia kola seed. | 2006 Jan |
|
Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats. | 2006 Jan 3 |
|
Gastroprotective and antioxidant effects of amiodarone on indomethacin-induced gastric ulcers in rats. | 2007 Nov |
|
Gastroprotective and anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats. | 2008 Winter |
|
Severe hypomagnesaemia due to lansoprazole. | 2009 |
|
Protective effect of histamine H2 receptor antagonist ranitidine against rotenone-induced apoptosis. | 2009 Nov |
|
Drug-induced aseptic meningitis, sensorineural hearing loss and vestibulopaty. | 2010 Sep |
|
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity. | 2011 Apr |
|
Attenuation of stress-induced gastric lesions by lansoprazole, PD-136450 and ranitidine in rats. | 2011 Mar |
|
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 |
|
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 |
|
Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds. | 2014 Dec 5 |
|
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
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 15:00:12 GMT 2023
by
admin
on
Fri Dec 15 15:00:12 GMT 2023
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Record UNII |
BK76465IHM
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29702
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100000090451
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BK76465IHM
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Ranitidine hydrochloride
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BK76465IHM
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1598405
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203136
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m9498
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47909
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C66506
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DTXSID201015892
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266-333-0
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CHEMBL1790041
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SUB04203MIG
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66357-59-3
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DBSALT000487
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8777
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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