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Identification
NameRoxatidine acetate
Accession NumberDB08806
TypeSmall Molecule
GroupsApproved
DescriptionRoxatidine acetate is a specific and competitive H2 receptor antagonist. It is currently approved in South Africa under the tradename Roxit.
Structure
Thumb
Synonyms
Aceroxatidine
Roxatidina
Roxatidine
Roxatidine acetate
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
RoxitNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Roxatidine acetate hydrochloride
ThumbNot applicableDBSALT000906
Categories
UNIIZUP3LSD0DO
CAS number78628-28-1
WeightAverage: 348.4366
Monoisotopic: 348.204907394
Chemical FormulaC19H28N2O4
InChI KeyInChIKey=SMTZFNFIKUPEJC-UHFFFAOYSA-N
InChI
InChI=1S/C19H28N2O4/c1-16(22)25-15-19(23)20-9-6-12-24-18-8-5-7-17(13-18)14-21-10-3-2-4-11-21/h5,7-8,13H,2-4,6,9-12,14-15H2,1H3,(H,20,23)
IUPAC Name
({3-[3-(piperidin-1-ylmethyl)phenoxy]propyl}carbamoyl)methyl acetate
SMILES
CC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassBenzylpiperidines
Direct ParentN-benzylpiperidines
Alternative Parents
Substituents
  • N-benzylpiperidine
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Acetate salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of disorders of the upper gastro-intestinal region that are due to an excess of hydrochloric acid in the gastric juice, i.e. duodenal ulcers, benign gastric ulcers. Also for prophylaxis of recurrent gastric and duodenal ulcers
PharmacodynamicsRoxatidine acetate suppresses the effect of histamine on the parietal cells of the stomach (H2-receptor antagonist). This suppressive action is dose-dependent. As a result, the production and secretion, particularly of gastric acid, are reduced. Roxatidine acetate has no antiandrogenic effects and does not influence drug-metabolizing enzymes in the liver.
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.
Related Articles
AbsorptionWell absorbed orally (80–90% bioavailability).
Volume of distributionNot Available
Protein binding5-7%
Metabolism

Roxatidine acetate is rapidly metabolised to the primary, active desacetyl metabolite.

Route of eliminationNot Available
Half life5-6 hours
ClearanceNot Available
ToxicityOral, mouse LD50: 1000 mg/kg
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Roxatidine acetate Action PathwayDrug actionSMP00734
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9475
Blood Brain Barrier+0.8366
Caco-2 permeable-0.6032
P-glycoprotein substrateSubstrate0.7781
P-glycoprotein inhibitor IInhibitor0.7868
P-glycoprotein inhibitor IINon-inhibitor0.675
Renal organic cation transporterNon-inhibitor0.645
CYP450 2C9 substrateNon-substrate0.7803
CYP450 2D6 substrateNon-substrate0.8415
CYP450 3A4 substrateSubstrate0.5264
CYP450 1A2 substrateNon-inhibitor0.9143
CYP450 2C9 inhibitorNon-inhibitor0.8237
CYP450 2D6 inhibitorNon-inhibitor0.6876
CYP450 2C19 inhibitorNon-inhibitor0.7797
CYP450 3A4 inhibitorNon-inhibitor0.9203
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6467
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9324
BiodegradationNot ready biodegradable0.5199
Rat acute toxicity2.0100 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8833
hERG inhibition (predictor II)Inhibitor0.5448
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point145-146 for HCl saltMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0612 mg/mLALOGPS
logP2.27ALOGPS
logP1.31ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.88ChemAxon
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.87 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.32 m3·mol-1ChemAxon
Polarizability39.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Product Insert [Link]
External Links
ATC CodesA02BA06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (1.19 MB)
Interactions
Drug Interactions
Drug
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Roxatidine acetate.
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Roxatidine acetate.
AmphetamineAmphetamine may decrease the sedative activities of Roxatidine acetate.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Roxatidine acetate.
BenzphetamineBenzphetamine may decrease the sedative activities of Roxatidine acetate.
Benzylpenicilloyl PolylysineRoxatidine acetate may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Roxatidine acetate.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Roxatidine acetate.
CefditorenThe serum concentration of Cefditoren can be decreased when it is combined with Roxatidine acetate.
CefpodoximeRoxatidine acetate can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
CefuroximeRoxatidine acetate can cause a decrease in the absorption of Cefuroxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
ChlorphentermineChlorphentermine may decrease the sedative activities of Roxatidine acetate.
CysteamineThe therapeutic efficacy of Cysteamine can be decreased when used in combination with Roxatidine acetate.
DabrafenibThe serum concentration of Dabrafenib can be decreased when it is combined with Roxatidine acetate.
DasatinibRoxatidine acetate can cause a decrease in the absorption of Dasatinib resulting in a reduced serum concentration and potentially a decrease in efficacy.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Roxatidine acetate.
DexmethylphenidateRoxatidine acetate can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
DextroamphetamineDextroamphetamine may decrease the sedative activities of Roxatidine acetate.
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Roxatidine acetate.
FosamprenavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Roxatidine acetate.
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Roxatidine acetate.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Roxatidine acetate.
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide may decrease the sedative activities of Roxatidine acetate.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Roxatidine acetate.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Roxatidine acetate.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Roxatidine acetate.
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Roxatidine acetate.
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Roxatidine acetate.
MephentermineMephentermine may decrease the sedative activities of Roxatidine acetate.
MesalazineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Roxatidine acetate.
MethamphetamineMethamphetamine may decrease the sedative activities of Roxatidine acetate.
MethylphenidateRoxatidine acetate can cause an increase in the absorption of Methylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Roxatidine acetate.
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Roxatidine acetate.
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Roxatidine acetate.
PhenterminePhentermine may decrease the sedative activities of Roxatidine acetate.
PosaconazoleThe serum concentration of Posaconazole can be decreased when it is combined with Roxatidine acetate.
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Roxatidine acetate.
RisedronateThe serum concentration of Risedronate can be increased when it is combined with Roxatidine acetate.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Roxatidine acetate.
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Roxatidine acetate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Histamine receptor activity
Specific Function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) si...
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular Weight:
40097.65 Da
References
  1. Agrawal SS, Alvin Jose M: Roxatidine, an H(2) receptor blocker, is an estrogenic compound--experimental evidence. Syst Biol Reprod Med. 2010 Aug;56(4):286-91. doi: 10.3109/19396368.2010.496894. [PubMed:20718616 ]
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Drug created on October 18, 2010 16:57 / Updated on August 17, 2016 12:24