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Details

Stereochemistry ACHIRAL
Molecular Formula C13H22N4O3S
Molecular Weight 314.4054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RANITIDINE

SMILES

CN/C(=C(\[H])/N(=O)=O)/NCCSCc1ccc(CN(C)C)o1

InChI

InChIKey=VMXUWOKSQNHOCA-LCYFTJDESA-N
InChI=1S/C13H22N4O3S/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/b13-9-

HIDE SMILES / InChI

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

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
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
Depression associated with ranitidine.
1986 Jul
Famotidine-associated mental confusion in elderly patients.
1988 Dec
Ranitidine and bradycardia.
1988 Mar
Ranitidine-induced confusion with concomitant morphine.
1988 Nov
A dog model for acetaminophen-induced fulminant hepatic failure.
1989 Feb
Mechanism of ranitidine associated anemia.
1989 Jun
Histamine release in the isolated vascularly perfused stomach of the rat: regulation by autoreceptors.
1989 Mar
Effects of histamine H2-receptor blockade on the cardiovascular reflex response to lower-body negative pressure in man.
1990 May
Ranitidine pharmacokinetics and adverse central nervous system reactions.
1992 Nov
[Aseptic meningitis after ranitidine treatment for systemic lupus erythematosus].
1999 Nov 13
Fatal hepatitis associated with ranitidine.
2000 Feb
Ranitidine-related Stevens-Johnson syndrome in patients with severe liver diseases: a report of two cases.
2001 Apr
Nephrotoxicity and hepatotoxicity of histamine H2 receptor antagonists.
2001 Jan
Depression or hypoactive delirium? A report of ciprofloxacin-induced mental disorder in a patient with chronic obstructive pulmonary disease.
2001 Jan-Feb
Healing and relapse rates in gastroesophageal reflux disease treated with the newer proton-pump inhibitors lansoprazole, rabeprazole, and pantoprazole compared with omeprazole, ranitidine, and placebo: evidence from randomized clinical trials.
2001 Jul
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
Management of heartburn in a large, randomized, community-based study: comparison of four therapeutic strategies.
2001 Jun
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 three H2-receptor antagonists (cimetidine, famotidine, ranitidine) on serum gastrin level.
2002
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
Ranitidine reduces ischemia/reperfusion-induced liver injury in rats by inhibiting neutrophil activation.
2002 Jun
Ranitidine treatment during a modest inflammatory response precipitates idiosyncrasy-like liver injury in rats.
2003 Oct
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
Lethal cardiomyopathy in epidermolysis bullosa associated with amitriptyline.
2005 Aug
Differential substrate and inhibitory activities of ranitidine and famotidine toward human organic cation transporter 1 (hOCT1; SLC22A1), hOCT2 (SLC22A2), and hOCT3 (SLC22A3).
2005 Dec
Role of histamine in airway remodeling of asthmatic guinea pig.
2005 Dec 25
Mechanisms of action of leptin in preventing gastric ulcer.
2005 Jul 21
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
A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters.
2005 Oct
Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes.
2006 Aug
In vitro availability of metformin in presence of h(2) receptor antagonists.
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
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.
2007 Jul 15
Gastroprotective and antioxidant effects of amiodarone on indomethacin-induced gastric ulcers in rats.
2007 Nov
Gastroprotective and antioxidant effects of montelukast on indomethacin-induced gastric ulcer in rats.
2007 Sep
Severe hypomagnesaemia due to lansoprazole.
2009
Drug-induced aseptic meningitis, sensorineural hearing loss and vestibulopaty.
2010 Sep
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.
2011 Feb
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
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
10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:44:33 UTC 2021
Edited
by admin
on Fri Jun 25 20:44:33 UTC 2021
Record UNII
884KT10YB7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RANITIDINE
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
RANITIDINE [VANDF]
Common Name English
RANITIDINE [WHO-DD]
Common Name English
RANITIDINE [MI]
Common Name English
RANITIDINE [MART.]
Common Name English
RANITIDINE [ORANGE BOOK]
Common Name English
RANITIDINE [USAN]
Common Name English
NSC-757851
Code English
RANITIDINE [HSDB]
Common Name English
RANITIDINE [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC A02BA02
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 17.1
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
NDF-RT N0000175784
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
WHO-ATC A02BA07
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
NDF-RT N0000000151
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
LIVERTOX 833
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
WHO-VATC QA02BA02
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
NCI_THESAURUS C29702
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
Code System Code Type Description
RXCUI
9143
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY RxNorm
IUPHAR
1234
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
EVMPD
SUB10258MIG
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
WIKIPEDIA
RANITIDINE
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
PUBCHEM
657345
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL1790041
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
EPA CompTox
66357-35-5
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
LACTMED
Ranitidine
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
DRUG CENTRAL
2358
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
DRUG BANK
DB00863
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
CAS
66357-35-5
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
MESH
D011899
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
FDA UNII
884KT10YB7
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
ECHA (EC/EINECS)
266-332-5
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
MERCK INDEX
M9498
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY Merck Index
HSDB
3925
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
NCI_THESAURUS
C29412
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
INN
4660
Created by admin on Fri Jun 25 20:44:33 UTC 2021 , Edited by admin on Fri Jun 25 20:44:33 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
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METABOLITE INACTIVE -> PARENT
MINOR
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
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URINE
METABOLITE INACTIVE -> PARENT
MINOR
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Route of Elimination PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ELDERLY: 3 - 4 HOURS

CHILDREN: 1.7 - 2.8 HOURS

ADULTS, RENAL IMPAIRMENT: 4.8 - 9.8 HOURS

MAXIMUM TOLERATED DOSE TOXICITY NON-ULCER INDIGESTION, PROPHYLAXIS AND TREATMENT: 300 MG/DAY

Volume of Distribution PHARMACOKINETIC
PROTEIN BINDING PHARMACOKINETIC