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Details

Stereochemistry ACHIRAL
Molecular Formula C13H22N4O3S
Molecular Weight 314.404
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RANITIDINE

SMILES

CNC(NCCSCC1=CC=C(CN(C)C)O1)=C[N+]([O-])=O

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 314.404
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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
Histamine and hepatic glutathione in the mouse.
1987 May 25
Fatal renal and hepatic toxicity after treatment with diltiazem.
1987 Nov 14
First-degree atrioventricular block in a young duodenal ulcer patient treated with a standard oral dose of ranitidine.
1988 Jul
Reversible chorea due to ranitidine and cimetidine.
1988 Jul 16
Ranitidine and bradycardia.
1988 Mar
Cardiac arrest associated with ranitidine.
1989 Aug 19
A dog model for acetaminophen-induced fulminant hepatic failure.
1989 Feb
Mechanism of ranitidine associated anemia.
1989 Jun
Ranitidine-induced chest pain.
1989 Mar
Histamine release in the isolated vascularly perfused stomach of the rat: regulation by autoreceptors.
1989 Mar
Seizures during concomitant treatment with theophylline and ranitidine: a case report.
1990 Oct-Dec
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
Ranitidine-induced acute dystonia.
1999 May
Fatal hepatitis associated with ranitidine.
2000 Feb
Gastroesophageal reflux in infants and children.
2001 Dec 1
Depression or hypoactive delirium? A report of ciprofloxacin-induced mental disorder in a patient with chronic obstructive pulmonary disease.
2001 Jan-Feb
Ranitidine-induced acute interstitial nephritis in a cadaveric renal allograft.
2001 Jul
Management of heartburn in a large, randomized, community-based study: comparison of four therapeutic strategies.
2001 Jun
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
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
Ranitidine treatment during a modest inflammatory response precipitates idiosyncrasy-like liver injury in rats.
2003 Oct
Involvement of substance P, CGRP and histamine in the hyperalgesia and cytokine upregulation induced by intraplantar injection of capsaicin in rats.
2004 Aug
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
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
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
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
Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats.
2006 Jan 3
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
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 anti-oxidative properties of ascorbic acid on indomethacin-induced gastric injuries in rats.
2008 Winter
Severe hypomagnesaemia due to lansoprazole.
2009
Synergistic drug-cytokine induction of hepatocellular death as an in vitro approach for the study of inflammation-associated idiosyncratic drug hepatotoxicity.
2009 Jun 15
Drug-induced aseptic meningitis, sensorineural hearing loss and vestibulopaty.
2010 Sep
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity.
2011 Apr
Hepatoprotective, antinociceptive and antioxidant activities of cimetidine, ranitidine and famotidine as histamine H2 receptor antagonists.
2011 Feb
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
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 Wed Jul 05 23:41:37 UTC 2023
Edited
by admin
on Wed Jul 05 23:41:37 UTC 2023
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 [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 [WHO-DD]
Common Name English
RANITIDINE [HSDB]
Common Name English
ranitidine [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC A02BA02
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 17.1
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
NDF-RT N0000175784
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
WHO-ATC A02BA07
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
NDF-RT N0000000151
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
LIVERTOX NBK548867
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
WHO-VATC QA02BA02
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
NCI_THESAURUS C29702
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
Code System Code Type Description
RXCUI
9143
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY RxNorm
IUPHAR
1234
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
CHEBI
8776
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
EVMPD
SUB10258MIG
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
DAILYMED
884KT10YB7
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
WIKIPEDIA
RANITIDINE
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
PUBCHEM
657345
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1790041
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045191
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
LACTMED
Ranitidine
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
NSC
757851
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
DRUG CENTRAL
2358
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
DRUG BANK
DB00863
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
CAS
66357-35-5
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
MESH
D011899
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
FDA UNII
884KT10YB7
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
266-332-5
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
MERCK INDEX
M9498
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY Merck Index
HSDB
3925
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
NCI_THESAURUS
C29412
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
INN
4660
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
SMS_ID
100000092215
Created by admin on Wed Jul 05 23:41:37 UTC 2023 , Edited by admin on Wed Jul 05 23:41:37 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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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