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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
Structure of RANITIDINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

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

1983
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

1983
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

1983
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

1983
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
Mental confusion as a side effect of ranitidine.
1986 Feb
Depression associated with ranitidine.
1986 Jul
Myofascial headache. Exacerbation of symptoms due to diflunisal and ranitidine therapy. A case report.
1987 Aug
Histamine and hepatic glutathione in the mouse.
1987 May 25
Mania associated with intravenous ranitidine therapy.
1987 Nov
Fatal renal and hepatic toxicity after treatment with diltiazem.
1987 Nov 14
Famotidine-associated mental confusion in elderly patients.
1988 Dec
Mania-like episodes associated with ranitidine.
1988 Feb
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
Ranitidine-induced confusion with concomitant morphine.
1988 Nov
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
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
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
Proton pump inhibitors versus H2-antagonists: a meta-analysis of their efficacy in treating bleeding peptic ulcer.
2001 Jul
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
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
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
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.
2003 Feb
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Intracerebroventricular effects of histaminergic agents on morphine-induced anxiolysis in the elevated plus-maze in rats.
2005 Nov
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of tiapride.
2005 Nov-Dec
Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats.
2006 Jan 3
Novel role of famotidine in downregulation of matrix metalloproteinase-9 during protection of ethanol-induced acute gastric ulcer.
2007 Jul 15
The role of tumor necrosis factor alpha in lipopolysaccharide/ranitidine-induced inflammatory liver injury.
2007 Nov
Severe hypomagnesaemia due to lansoprazole.
2009
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
10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:12 GMT 2023
Record UNII
BK76465IHM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RANITIDINE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
ZANTAC
Brand Name English
AH 19065
Code English
RANITIDINE HYDROCHLORIDE [JAN]
Common Name English
RANITIDINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
RANITIDINE HYDROCHLORIDE [USP-RS]
Common Name English
RANITIDINE HYDROCHLORIDE [MI]
Common Name English
AH-19065
Code English
RANITIDINE HYDROCHLORIDE [MART.]
Common Name English
TALADINE
Brand Name English
RANITIDINE HCL
Common Name English
RANITIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
RANITIDINE HYDROCHLORIDE [VANDF]
Common Name English
RANITIDINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
Ranitidine hydrochloride [WHO-DD]
Common Name English
RANITIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
N-(2-(((5-((DIMETHYLAMINO)METHYL)-2-FURANYL)METHYL)THIO)ETHYL)-N'-METHYL-2-NITRO-1,1-ETHENEDIAMINE, HYDROCHLORIDE
Systematic Name English
1,1-ETHENEDIAMINE, N-(2-(((5-((DIMETHYLAMINO)METHYL)-2-FURANYL)METHYL)THIO)ETHYL)-N'-METHYL-2-NITRO-, MONOHYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29702
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
Code System Code Type Description
SMS_ID
100000090451
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
DAILYMED
BK76465IHM
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
WIKIPEDIA
Ranitidine hydrochloride
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
FDA UNII
BK76465IHM
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
RS_ITEM_NUM
1598405
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
RXCUI
203136
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m9498
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY Merck Index
PUBCHEM
47909
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
NCI_THESAURUS
C66506
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID201015892
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
266-333-0
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL1790041
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
EVMPD
SUB04203MIG
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
CAS
66357-59-3
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
DRUG BANK
DBSALT000487
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
CHEBI
8777
Created by admin on Fri Dec 15 15:00:12 GMT 2023 , Edited by admin on Fri Dec 15 15:00:12 GMT 2023
PRIMARY
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