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

• ChemBase ID: 803
• Molecular Formular: C8H15N7O2S3
• Molecular Mass: 337.4454
• Monoisotopic Mass: 337.04493576
• SMILES: S(CC/C(=N/S(=O)(=O)N)/N)Cc1nc(sc1)N=C(N)N
• Canonical SMILES: NC(=Nc1scc(n1)CSCC/C(=N/S(=O)(=O)N)/N)N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (Z)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropimidamide; 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropanimidamide
• IUPAC Traditional name: brolin; famotidine; (Z)-3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]-N'-sulfamoylpropimidamide
• Brand Name: Amfamox; Antodine; Apo-Famotidine; Apogastine; Bestidine; Blocacid; Brolin; Cepal; Confobos; Cronol; Cuantin; Dibrit 40; Digervin; Dinul; Dipsin; Dispromil; Dispronil; Duovel; Durater; Evatin; Fadin; Fadine; Fadyn; Fagastine; Famo; Famocid; Famodar; Famodil; Famodin; Famodine; Famogard; Famonit; Famopsin; Famos; Famosan; Famotal; Famotep; Famotin; Famovane; Famowal; Famox; Famoxal; Famtac; Famulcer; Fanobel; Fanosin; Fanox; Farmotex; Ferotine; Fibonel; Fluxid; Fudone; Ganor; Gaster; Gastridan; Gastridin; Gastrion; Gastro; Gastrodomina; Gastrofam; Gastropen; Gastrosidin; H2 Bloc; Hacip; Huberdina; Ingastri; Invigan; Lecedil; Logos; Mensoma; Midefam; Mosul; Motiax; Muclox; Mylanta AR; Neocidine; Nevofam; Notidin; Novo-Famotidine; Nu-Famotidine; Nulceran; Nulcerin; Panalba; Pepcid; Pepcid AC; Pepcid RPD; Pepcidin; Pepcidin Rapitab; Pepcidina; Pepcidine; Pepdif; Pepdine; Pepdul; Pepfamin; Peptan; Peptidin; Peptifam; Pepzan; Purifam; Quamatel; Quamtel; Renapepsa; Restadin; Rogasti; Rubacina; Sedanium-R; Sigafam; Supertidine; Tairal; Tamin; Tipodex; Topcid; Ulcatif; Ulceprax; Ulcofam; Ulfagel; Ulfam; Ulfamid; Ulfinol; Ulgarine; Vagostal; Weimok; Whitidin; Yamarin
• Synonyms: N-[(1S)-1-(Aminocarbonyl)-4-[(2-fluoro-1-iminoethyl)amino]butyl]benzamide; F-Amidine; Famotidina [Spanish]; Famotidinum [Latin]; Famotidine; Amifatidine; Famodil; Ganor; Gaster; Gastridin; Motiax; Pepcid; Pepcidac; Pepcidine; Pepdine; Pepdul; Famotidine

Database IDs

• CAS Number: 877617-45-3; 76824-35-6
• PubChem SID: 160964266; 46507397
• PubChem CID: 5702160

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.287259
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.40545
• LogD (pH = 7.4): -2.6732495
• Log P: -1.9501336
• Molar Refractivity: 80.462 cm^3
• Polarizability: 30.774752 Å^3
• Polar Surface Area: 175.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.2
• LOG S: -3.1
• Solubility (Water): 2.71e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.1 mg/mL
• Hydrophobicity(logP): -2.1

Pharmacology Properties

• Mechanism of Action: Gastric secretion inhibitor; Histamine H 2 receptor antagonist; Weak pepsin inhibitor

Product Information

• Application(s): Antiviral agent; Suggested beneficial effect in treatment of schizophrenia.; Used in treatment of gastric and duodenal ulcers, gastro-oesophageal reflux disease and Zollinger-Ellison syndrome.

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

Toronto Research Chemicals - 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

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