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Identification
NameRanitidine
Accession NumberDB00863  (APRD00254)
Typesmall molecule
Groupsapproved
Description

A non-imidazole blocker of those histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
RANNot AvailableNot Available
Salts
Name/CAS Structure Properties
Ranitidine Hydrochloride
66357-59-3
Thumb
  • InChI Key: GGWBHVILAJZWKJ-KJEVSKRMSA-N
  • Monoisotopic Mass: 350.117939019
  • Average Mass: 350.865
DBSALT000487
Brand names
NameCompany
AlquenNot Available
CoralenNot Available
GastrolavNot Available
GastrosedolNot Available
KuracidNot Available
Nu-RanitNot Available
Pep-RaniNot Available
PtinolinNot Available
RaniberlNot Available
RaniblocNot Available
RanicuxNot Available
RanidilNot Available
RanidinNot Available
RanidineNot Available
RaniduraNot Available
RanifurNot Available
RanigastNot Available
RaniplexNot Available
RanisanNot Available
RanitabNot Available
RaniticNot Available
RanitidinNot Available
RanitinNot Available
RanitineNot Available
RanobelNot Available
RantacidNot Available
RanuberNot Available
RenatacNot Available
SostrilNot Available
TanidinaNot Available
ToriolNot Available
UlcodinNot Available
ZandidNot Available
ZantacNot Available
ZanticNot Available
Brand mixtures
Brand NameIngredients
Tritecranitidine +bismuth + citrate salt
Categories
CAS number66357-35-5
WeightAverage: 314.404
Monoisotopic: 314.14126128
Chemical FormulaC13H22N4O3S
InChI KeyVMXUWOKSQNHOCA-UKTHLTGXSA-N
InChI
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+
IUPAC Name
dimethyl[(5-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine
SMILES
CN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassFurans
SubclassNot Available
Direct parentFurans
Alternative parentsNitro Compounds; Tertiary Amines; Nitronic Acids; Polyamines; Organic Oxoazanium Compounds; Thioethers
Substituentsnitronic acid; nitro compound; tertiary amine; organic oxoazanium; polyamine; thioether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the furans. These are compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms.
Pharmacology
IndicationUsed in the treatment of peptic ulcer disease (PUD), dyspepsia, stress ulcer prophylaxis, and gastroesophageal reflux disease (GERD).
PharmacodynamicsRanitidine is a histamine H2-receptor antagonist similar to cimetidine and famotidine. An H2-receptor antagonist, often shortened to H2 antagonist, is a drug used to block the action of histamine on parietal cells in the stomach, decreasing acid production by these cells. These drugs are used in the treatment of dyspepsia, however their use has waned since the advent of the more effective proton pump inhibitors. Like the H1-antihistamines, the H2 antagonists are inverse agonists rather than true receptor antagonists.
Mechanism of actionThe H2 antagonists are competitive inhibitors of histamine at the parietal cell H2 receptor. They suppress the normal secretion of acid by parietal cells and the meal-stimulated secretion of acid. They accomplish this by two mechanisms: histamine released by ECL cells in the stomach is blocked from binding on parietal cell H2 receptors which stimulate acid secretion, and other substances that promote acid secretion (such as gastrin and acetylcholine) have a reduced effect on parietal cells when the H2 receptors are blocked.
AbsorptionApproximately 50% bioavailability orally.
Volume of distribution
  • 1.4 L/kg
  • 1.76 L/kg [clinically significant renal function impairment (creatinine clearance 25 to 35 mL/min)]
Protein binding15%
Metabolism

Hepatic. Ranitidine is metabolized to the N-oxide, S-oxide, and N-desmethyl metabolites, accounting for approximately 4%, 1%, and 1% of the dose, respectively.

Route of eliminationThe principal route of excretion is the urine (active tubular excretion, renal clearance 410mL/min), with approximately 30% of the orally administered dose collected in the urine as unchanged drug in 24 hours.
Half life2.8-3.1 hours
Clearance
  • 29 mL/min [clinically significant renal function impairment]
  • 3 mL/min/Kg [neonatal patients]
ToxicityLD50=77mg/kg (orally in mice). Symptoms of overdose include muscular tremors, vomiting, and rapid respiration.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9936
Blood Brain Barrier - 0.8783
Caco-2 permeable - 0.5838
P-glycoprotein substrate Substrate 0.8527
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.8893
Renal organic cation transporter Non-inhibitor 0.8177
CYP450 2C9 substrate Non-substrate 0.7702
CYP450 2D6 substrate Substrate 0.7414
CYP450 3A4 substrate Non-substrate 0.5565
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7819
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.8077
Biodegradation Not ready biodegradable 0.9249
Rat acute toxicity 2.0903 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.8628
hERG inhibition (predictor II) Non-inhibitor 0.8734
Pharmacoeconomics
Manufacturers
  • Dr reddys laboratories ltd
  • Genpharm inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Bedford laboratories div ben venue laboratories inc
  • Ben venue laboratories inc
  • Alpharma us pharmaceuticals division
  • Amneal pharmaceuticals
  • Apotex inc
  • Aurobindo pharma usa inc
  • Cypress pharmaceutical inc
  • Pharmaceutical assoc inc div beach products
  • Ranbaxy laboratories ltd
  • Vintage pharmaceuticals inc
  • Wockhardt ltd
  • Boehringer ingelheim pharmaceuticals inc
  • Amneal pharmaceuticals ny llc
  • Boehringer ingelheim corp
  • Contract pharmacal corp
  • Dr reddys laboratories inc
  • Glenmark generics inc usa
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • L perrigo co
  • Ranbaxy pharmaceuticals inc
  • Torpharm inc
  • Watson laboratories inc
  • Wockhardt americas inc
  • Boehringer ingelheim
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous
SolutionOral
TabletOral
Prices
Unit descriptionCostUnit
Zantac 300 mg tablet7.96USDtablet
Ranitidine hcl powder5.2USDg
Zantac EFFERdose 25 mg Effervescent Tabs4.18USDtab
Zantac 25 efferdose tablet4.02USDtablet
Zantac 150 mg tablet3.11USDtablet
Ranitidine HCl 300 mg capsule2.85USDcapsule
Ranitidine HCl 300 mg tablet2.79USDtablet
Ranitidine 300 mg tablet2.69USDtablet
Ranitidine hcl 25 mg/ml vial2.0USDml
Zantac 25 mg/ml vial2.0USDml
Ranitidine HCl 150 mg capsule1.58USDcapsule
Zantac 25 mg/ml1.58USDml
Ranitidine HCl 150 mg tablet1.54USDtablet
Ranitidine 150 mg tablet1.48USDtablet
Ranitidine 25 mg/ml1.26USDml
Ranitidine HCl 15 mg/ml Syrup1.0USDml
Ratio-Ranitidine 300 mg Tablet0.82USDtablet
Apo-Ranitidine 300 mg Tablet0.82USDtablet
Co Ranitidine 300 mg Tablet0.82USDtablet
Mylan-Ranitidine 300 mg Tablet0.82USDtablet
Nu-Ranit 300 mg Tablet0.82USDtablet
Pms-Ranitidine 300 mg Tablet0.82USDtablet
Ran-Ranitidine 300 mg Tablet0.82USDtablet
Zantac 15 mg/ml Syrup0.81USDml
Zantac 75 tablet0.49USDtablet
Apo-Ranitidine 150 mg Tablet0.42USDtablet
Co Ranitidine 150 mg Tablet0.42USDtablet
Mylan-Ranitidine 150 mg Tablet0.42USDtablet
Nu-Ranit 150 mg Tablet0.42USDtablet
Pms-Ranitidine 150 mg Tablet0.42USDtablet
Ran-Ranitidine 150 mg Tablet0.42USDtablet
Ratio-Ranitidine 150 mg Tablet0.42USDtablet
Novo-Ranidine 300 mg Tablet0.38USDtablet
Phl-Ranitidine 300 mg Tablet0.38USDtablet
Sandoz Ranitidine 300 mg Tablet0.38USDtablet
Zantac 300 mg Tablet0.38USDtablet
Zantac 75 mg tablet0.28USDtablet
Wal-zan 75 mg tablet0.27USDtablet
Zantac 15 mg/ml Solution0.23USDml
Ranitidine hcl 75 mg tablet0.22USDtablet
Sm acid reducer 75 mg tablet0.22USDtablet
Acid reducer 150 mg tablet0.2USDtablet
Wal-zan 75 tablet0.2USDtablet
Novo-Ranidine 150 mg Tablet0.19USDtablet
Phl-Ranitidine 150 mg Tablet0.19USDtablet
Sandoz Ranitidine 150 mg Tablet0.19USDtablet
Zantac 150 mg Tablet0.19USDtablet
CVS Pharmacy ranitidine 75 mg tablet0.15USDtablet
Apo-Ranitidine 15 mg/ml Solution0.12USDml
Novo-Ranidine 15 mg/ml Solution0.12USDml
Acid reducer 75 mg tablet0.11USDtablet
CVS Pharmacy acid reducer 75 mg tablet0.11USDtablet
Qc ranitidine 75 mg tablet0.07USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States50987151993-12-202010-12-20
United States51026651992-12-232009-12-23
Canada13326101994-10-182011-10-18
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point69-70 °CPhysProp
water solubility24.7 mg/mLNot Available
logP0.27SANGSTER (1993)
Caco2 permeability-6.31ADME Research, USCD
Predicted Properties
PropertyValueSource
water solubility7.95e-02 g/lALOGPS
logP0.79ALOGPS
logP0.98ChemAxon
logS-3.6ALOGPS
pKa (strongest basic)8.08ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area86.26ChemAxon
rotatable bond count10ChemAxon
refractivity95.15ChemAxon
polarizability33.58ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

John W. Clitherow, “Intermediates in the preparation of ranitidine.” U.S. Patent US4413135, issued November, 1981.

US4413135
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00422
PubChem Compound3001055
PubChem Substance46505543
ChemSpider2272523
BindingDB22893
ChEBI8776
ChEMBLCHEMBL1790041
Therapeutic Targets DatabaseDAP000340
PharmGKBPA451224
IUPHAR1234
Guide to Pharmacology1234
Drug Product Database740748
RxListhttp://www.rxlist.com/cgi/generic2/ranitbc.htm
Drugs.comhttp://www.drugs.com/ranitidine.html
WikipediaRanitidine
ATC CodesA02BA02A02BA07
AHFS Codes
  • 56:28.12
PDB EntriesNot Available
FDA labelshow(247 KB)
MSDSshow(73.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolRanitidine may increase the anticoagulant effect of acenocoumarol. (Conflicting evidence)
AnisindioneRanitidine may increase the anticoagulant effect of anisindione. (Conflicting evidence)
AtazanavirRanitidine may decrease the levels/effects of atazanavir.
CefditorenH2-Antagonists such as ranitidine may decrease the serum concentration of cefditoren. Cefditoren prescribing information recommends to avoid concomitant use with H2-antagonists (eg, famotidine, ranitidine) and antacids as well. Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of H2-antagonists can not be avoided.
DabrafenibH2-receptor antagonists may alter the solubility of dabrafenib and reduce its bioavailability.
DasatinibRanitidine may decrease the serum level of dasatinib.
DicoumarolRanitidine may increase the anticoagulant effect of dicumarol. (Conflicting evidence)
ItraconazoleThe H2-receptor antagonist, ranitidine, may decrease the absorption of itraconazole.
KetoconazoleThe H2-receptor antagonist, ranitidine, may decrease the absorption of ketoconazole.
ProcainamideThe histamine H2-receptor antagonist, ranitidine, may increase the effect of procainamide.
RilpivirineHistamine-2 receptor antagonists increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
TolazolineAnticipated loss of efficacy of tolazoline
VismodegibVismodegib serum concentrations may be decreased by histamine 2 receptor antagonists such as ranitidine.
WarfarinRanitidine may increase the anticoagulant effect of warfarin. (Conflicting evidence)
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take without regard to meals.

Targets

1. Histamine H2 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H2 receptor P25021 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Pattichis K, Louca LL: Histamine, histamine H2-receptor antagonists, gastric acid secretion and ulcers: an overview. Drug Metabol Drug Interact. 1995;12(1):1-36. Pubmed

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. Pubmed

2. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Lentz KA, Polli JW, Wring SA, Humphreys JE, Polli JE: Influence of passive permeability on apparent P-glycoprotein kinetics. Pharm Res. 2000 Dec;17(12):1456-60. Pubmed
  2. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed
  3. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. Pubmed
  4. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. Pubmed

3. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Tahara H, Kusuhara H, Chida M, Fuse E, Sugiyama Y: 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. J Pharmacol Exp Ther. 2006 Mar;316(3):1187-94. Epub 2005 Nov 16. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12