CAS 76824-35-6|CAS 877617-45-3|Rubacina|Dinul|Pepzan|Sedanium-R|Fanox|H2 Bloc|Nulcerin|Gaster|Pepdul|Renapepsa|Panalba|Famonit|Amfamox|Famotep|Ulfagel|Pepdine|Novo-Famotidine|Ulfinol|Famos|Pepcid AC...

General Information

Structure

Molecular Formula

C₈H₁₅N₇O₂S₃

Molecular Mass

337.4454

Exact Mass

337.04493576

Charge

InChI

InChI=1S/C8H15N7O2S3/c9-6(15-20(12,16)17)1-2-18-3-5-4-19-8(13-5)14-7(10)11/h4H,1-3H2,(H2,9,15)(H2,12,16,17)(H4,10,11,13,14)

InChIKey

XUFQPHANEAPEMJ-UHFFFAOYSA-N

Canonic Smiles

NC(=Nc1scc(n1)CSCCC(=NS(=O)(=O)N)N)N

Isomeric Smiles

S(CC/C(=N/S(=O)(=O)N)/N)Cc1nc(sc1)N=C(N)N

Calculated Properties

JChem

LogD (pH = 7.4)

-2.67

LogD (pH = 5.5)

-3.41

Log P

-1.95

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.38

Polar Surface Area

175.83

Polarizability

31.66

Molar Refractivity

80.46

LOG S

-1.81

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

RubacinaDinulPepzanSedanium-RFanoxH2 BlocNulcerinGasterPepdulRenapepsaPanalbaFamonitAmfamoxFamotepUlfagelPepdineNovo-FamotidineUlfinolFamosPepcid ACCronolUlgarineGastrodominaLogosHuberdinaDispronilGastrionNu-FamotidineUlfamidPepdifNevofamIngastriFibonelFamotinFamulcerConfobosQuamtelDipsinFadynBrolinPepcid RPDMylanta ARMosulFamovaneMensomaNulceranDigervinDispromilPepcidin RapitabGanorEvatinQuamatelTipodexInviganGastridanFamtacFamoGastridinBestidineApogastineFadinCepalPepcidinaPeptidinFanosinAntodineTaminFamodineFanobelHacipUlcatifTopcidWhitidinMidefamFluxidFudoneGastrofamTairalDibrit 40FamopsinSigafamUlfamRestadinPurifamPepcidFamodinFagastineFamocidFamodarDuovelMucloxWeimokPepcidinPepfaminRogastiGastropenBlocacidFamodilFamotalSupertidineUlcofamNeocidinePeptifamMotiaxFarmotexGastrosidinFamowalFerotineLecedilFamoxPepcidinePeptanFadineCuantinYamarinFamogardDuraterApo-FamotidineVagostalUlcepraxNotidinGastroFamosanFamoxal

IUPAC Traditional name

famotidine brolin (Z)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropimidamide pepcid

Synonyms

Famotidinum [Latin]FamotidineFamotidina [Spanish]N-[(1S)-1-(Aminocarbonyl)-4-[(2-fluoro-1-iminoethyl)amino]butyl]benzamidePepdulPepcidineFamodilPepcidacF-AmidineGanorGasterFamotidinePepcidPepdineAmifatidineGastridinMotiax3-(((2-((Aminoiminomethyl)amino)-4-thiazolyl)methyl)thio)-N-(aminosulfonyl)propanimidamide(1-Amino-3-(((2-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)propylidene)sulfamide3-(((2-((Diaminomethylene)amino)-4-thiazolyl)methyl)thio)-N(sup 2)-sulfamoylpropionamidinefamotidineN-Sulfamoyl-3-((2-guanidinothiazol-4-yl)methylthio)propionamide

IUPAC name

3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropanimidamide (Z)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropimidamide

International Nonproprietary Name (INN)

famotidinafamotidinefamotidinum

Names and Identifiers

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-2.1

Solubility

1.1 mg/mL

Safety Information

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Application(s)

Used in treatment of gastric and duodenal ulcers, gastro-oesophageal reflux disease and Zollinger-Ellison syndrome.

Antiviral agent

Suggested beneficial effect in treatment of schizophrenia.

Pharmacology Properties

Mechanism of Action

Histamine H 2 receptor antagonist

Gastric secretion inhibitor

Weak pepsin inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00927

Drug Groups

approved

Description

A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion. [PubChem]

Indication

For the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD).

Pharmacology

Famotidine, a competitive histamine H₂-receptor antagonist, is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Famotidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Famotidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.

Toxicity

Intravenous, mouse: LD₅₀ = 244.4mg/kg; Oral, mouse: LD₅₀ = 4686 mg/kg. Symptoms of overdose include emesis, restlessness, pallor of mucous membranes or redness of mouth and ears, hypotension, tachycardia and collapse.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

The bioavailability of oral doses is 40-45%.

Half Life

2.5-3.5 hours

Protein Binding

15-20%

Elimination

Renal clearance is 250-450 mL/min, indicating some tubular excretion.

Clearance

* renal cl=250-450 mL/min

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

TRC

F101250

An inhibitor of Peptidyl arginine deiminase 4 (PAD4) activity with an IC50 value of 21.6 μM in an in vitro activity assay. It irreversibly inactivates (kinact/KI = 3,000 M-1min-1) PAD4 by covalently modifying an active site cysteine that is important for

Molecule Details

References

PubChem Literature

From Data Sources

• Hill, J.A. et al.: J. Immunol., 171, 538 (2009)

• Jones, J.E. et al.: Curr. Opin. Drug Discov. Dev., 12, 616 (2009)

• Luo, Y. et al.: Biochemistry, 45, 11727 (2009)

• Knuckley, B. et al.: Biochemistry, 49, 1 (2009)

• Slack, J.L. et al.: Cell. Mol. Life Sci.,

• Oyewumi, L.K. et al., J. Psychiatry Neurosci., 1994, 19, 145; 20, 239, (use)

• J. Int. Med. Res., Suppl. 1, 1989, 17, 1A, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FAB500

• Katsura, Y. et al., Chem. Pharm. Bull., 1992, 40, 2432, (analogues, activity)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1192

• Golic, L. et al., Acta Cryst. C, 1989, 45, 1381, (cryst struct)

• Ger. Pat., 1980, Yamanouchi, 3 008 056; CA, 94, 156916e, (synth, pharmacol)

• Takagi, T. et al., Arch. Int. Pharmacodyn. Ther., 1982, 256, 49, (pharmacol)

• Wanwimolruk, S. et al., J. Chromatogr., 1991, 572, 227, (hplc)

• Imai, Y. et al., Biomed. Chromatogr., 1992, 6, 222, (hplc)

• Langtry, H.D. et al., Drugs, 1989, 38, 551, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 1216, (synonyms)

References

Bioactivity

PubChem BioAssay

Bioactivity