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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:48:09
Primary Accession Number DB00927
Secondary Accession Number
  • APRD00296
Name Famotidine
Drug Type
  • Approved
  • Small Molecule
Description A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion. [PubChem]
Synonyms
  1. Famotidina [Spanish]
  2. Famotidinum [Latin]
Brand Names
  1. Amfamox
  2. Antodine
  3. Apo-Famotidine
  4. Apogastine
  5. Bestidine
  6. Blocacid
  7. Brolin
  8. Cepal
  9. Confobos
  10. Cronol
  11. Cuantin
  12. Dibrit 40
  13. Digervin
  14. Dinul
  15. Dipsin
  16. Dispromil
  17. Dispronil
  18. Duovel
  19. Durater
  20. Evatin
  21. Fadin
  22. Fadine
  23. Fadyn
  24. Fagastine
  25. Famo
  26. Famocid
  27. Famodar
  28. Famodil
  29. Famodin
  30. Famodine
  31. Famogard
  32. Famonit
  33. Famopsin
  34. Famos
  35. Famosan
  36. Famotal
  37. Famotep
  38. Famotin
  39. Famovane
  40. Famowal
  41. Famox
  42. Famoxal
  43. Famtac
  44. Famulcer
  45. Fanobel
  46. Fanosin
  47. Fanox
  48. Farmotex
  49. Ferotine
  50. Fibonel
  51. Fluxid
  52. Fudone
  53. Ganor
  54. Gaster
  55. Gastridan
  56. Gastridin
  57. Gastrion
  58. Gastro
  59. Gastrodomina
  60. Gastrofam
  61. Gastropen
  62. Gastrosidin
  63. H2 Bloc
  64. Hacip
  65. Huberdina
  66. Ingastri
  67. Invigan
  68. Lecedil
  69. Logos
  70. Mensoma
  71. Midefam
  72. Mosul
  73. Motiax
  74. Muclox
  75. Mylanta AR
  76. Neocidine
  77. Nevofam
  78. Notidin
  79. Novo-Famotidine
  80. Nu-Famotidine
  81. Nulceran
  82. Nulcerin
  83. Panalba
  84. Pepcid
  85. Pepcid AC
  86. Pepcid RPD
  87. Pepcidin
  88. Pepcidin Rapitab
  89. Pepcidina
  90. Pepcidine
  91. Pepdif
  92. Pepdine
  93. Pepdul
  94. Pepfamin
  95. Peptan
  96. Peptidin
  97. Peptifam
  98. Pepzan
  99. Purifam
  100. Quamatel
  101. Quamtel
  102. Renapepsa
  103. Restadin
  104. Rogasti
  105. Rubacina
  106. Sedanium-R
  107. Sigafam
  108. Supertidine
  109. Tairal
  110. Tamin
  111. Tipodex
  112. Topcid
  113. Ulcatif
  114. Ulceprax
  115. Ulcofam
  116. Ulfagel
  117. Ulfam
  118. Ulfamid
  119. Ulfinol
  120. Ulgarine
  121. Vagostal
  122. Weimok
  123. Whitidin
  124. Yamarin
Brand Mixtures Not Available
Chemical IUPAC Name 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide
Chemical Formula C8H15N7O2S3
Chemical Structure Structure
CAS Registry Number 76824-35-6
InChI Identifier InChI=1/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)/f/h9-12H2
InChI Key XUFQPHANEAPEMJ-DJLXYOOQCQ
KEGG Drug D00318 Link Image
KEGG Compound Not Available
PubChem Compound 3325 Link Image
PubChem Substance 191368 Link Image
ChEBI ID Not Available
PharmGKB ID PA449586 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02242327 Link Image
RxList Link http://www.rxlist.com/cgi/generic/famot.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pep1325.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Famotidine Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference H. Yasufumi et al.; U.S. Pat. 4,283,408 (1981)
Average Molecular Weight 337.4450
Monoisotopic Molecular Weight 337.0449
State Solid
Melting Point 163-164 oC
Experimental Water Solubility 1.1 mg/mL Source: PhysProp
Predicted Water Solubility 2.71e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -2.1 Source: PhysProp
Predicted LogP -0.20 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.10 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES N\C(N)=N\C1=NC(CSCC\C(N)=N\S(N)(=O)=O)=CS1
Canonical SMILES NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1
Drug Category
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
ATC Codes
AHFS Codes
  • 56:28.12
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.
Mechanism of Action Famotidine binds competitively to H2-receptors located on the basolateral membrane of the parietal cell, blocking histamine affects. This competitive inhibition results in reduced basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin.
Absorption The bioavailability of oral doses is 40-45%.
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.
Protein Binding 15-20%
Biotransformation Hepatic.
Half Life 2.5-3.5 hours
Dosage Forms
Form Route
Solution Intravenous
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Enoxacin The agent decreases the absorption of enoxacin
Itraconazole The anti-H2 decreases the absorption of the imidazole
Ketoconazole The anti-H2 decreases the absorption of the imidazole
Food Interactions
  • Avoid alcohol.
  • Limit caffeine intake.
  • Take without regard to meals, food may slightly increase the product's bioavailability.
Pathways
Name SMPDB Link KEGG Link
Famotidine Pathway SMP00231 Link Image
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
  4. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
Targets
  1. Histamine H2 receptor
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 124
Target 1 Name Histamine H2 receptor
Target 1 Synonyms
  1. Gastric receptor I
  2. H2R
Target 1 Gene Name HRH2
Target 1 Protein Sequence >Histamine H2 receptor 
MAPNGTASSFCLDSTACKITITVVLAVLILITVAGNVVVCLAVGLNRRLRNLTNCFIVSL
AITDLLLGLLVLPFSAIYQLSCKWSFGKVFCNIYTSLDVMLCTASILNLFMISLDRYCAV
MDPLRYPVLVTPVRVAISLVLIWVISITLSFLSIHLGWNSRNETSKGNHTTSKCKVQVNE
VYGLVDGLVTFYLPLLIMCITYYRIFKVARDQAKRINHISSWKAATIREHKATVTLAAVM
GAFIICWFPYFTAFVYRGLRGDDAINEVLEAIVLWLGYANSALNPILYAALNRDFRTGYQ
QLFCCRLANRNSHKTSLRSNASQLSRTQSREPRQQEEKPLKLQVWSGTEVTAPQGATDR
Target 1 Number of Residues 364
Target 1 Molecular Weight 40099
Target 1 Theoretical pI 9.39
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 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) signaling pathway
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 23-44
  • 58-81
  • 93-114
  • 135-159
  • 181-204
  • 235-258
  • 268-289
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 184088 Link Image
Target 1 UniProtKB/Swiss-Prot ID P25021 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1080 bp 
ATGGCACCCAATGGCACAGCCTCTTCCTTTTGCCTGGACTCTACCGCATGCAAGATCACC
ATCACCGTGGTCCTTGCGGTCCTCATCCTCATCACCGTTGCTGGCAATGTGGTCGTCTGT
CTGGCCGTGGGCTTGAACCGCCGGCTCCGCAACCTGACCAATTGTTTCATCGTGTCCTTG
GCTATCACTGACCTGCTCCTCGGCCTCCTGGTGCTGCCCTTCTCTGCCATCTACCAGCTG
TCCTGCAAGTGGAGCTTTGGCAAGGTCTTCTGCAATATCTACACCAGCCTGGATGTGATG
CTCTGCACAGCCTCCATTCTTAACCTCTTCATGATCAGCCTCGACCGGTACTGCGCTGTC
ATGGACCCACTGCGGTACCCTGTGCTGGTCACCCCAGTTCGGGTCGCCATCTCTCTGGTC
TTAATTTGGGTCATCTCCATTACCCTGTCCTTTCTGTCTATCCACCTGGGGTGGAACAGC
AGGAACGAGACCAGCAAGGGCAATCATACCACCTCTAAGTGCAAAGTCCAGGTCAATGAA
GTGTACGGGCTGGTGGATGGGCTGGTCACCTTCTACCTCCCGCTACTGATCATGTGCATC
ACCTACTACCGCATCTTCAAGGTCGCCCGGGATCAGGCCAAGAGGATCAATCACATTAGC
TCCTGGAAGGCAGCCACCATCAGGGAGCACAAAGCCACAGTGACACTGGCCGCCGTCATG
GGGGCCTTCATCATCTGCTGGTTTCCCTACTTCACCGCGTTTGTGTACCGTGGGCTGAGA
GGGGATGATGCCATCAATGAGGTGTTAGAAGCCATCGTTCTGTGGCTGGGCTATGCCAAC
TCAGCCCTGAACCCCATCCTGTATGCTGCGCTGAACAGAGACTTCCGCACCGGGTACCAA
CAGCTCTTCTGCTGCAGGCTGGCCAACCGCAACTCCCACAAAACTTCTCTGAGGTCCAAC
GCCTCTCAGCTGTCCAGGACCCAAAGCCGAGAACCCAGGCAACAGGAAGAGAAACCCCTG
AAGCTCCAGGTGTGGAGTGGGACAGAAGTCACGGCCCCCCAGGGAGCCACAGACAGGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH2 Link Image
Target 1 GenAtlas ID HRH2 Link Image
Target 1 HGNC ID HGNC:5183 Link Image
Target 1 Chromosome Location 5
Target 1 Locus 5q35.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Murakami H, Sun-Wada GH, Matsumoto M, Nishi T, Wada Y, Futai M: Human histamine H2 receptor gene: multiple transcription initiation and tissue-specific expression. FEBS Lett. 1999 May 28;451(3):327-31. [PubMed Link Image]
  2. Gantz I, Munzert G, Tashiro T, Schaffer M, Wang L, DelValle J, Yamada T: Molecular cloning of the human histamine H2 receptor. Biochem Biophys Res Commun. 1991 Aug 15;178(3):1386-92. [PubMed Link Image]
  3. Nishi T, Koike T, Oka T, Maeda M, Futai M: Identification of the promoter region of the human histamine H2-receptor gene. Biochem Biophys Res Commun. 1995 May 16;210(2):616-23. [PubMed Link Image]
  4. Orange PR, Heath PR, Wright SR, Pearson RC: Allelic variations of the human histamine H2 receptor gene. Neuroreport. 1996 May 17;7(7):1293-6. [PubMed Link Image]
  5. Del Valle J, Gantz I: Novel insights into histamine H2 receptor biology. Am J Physiol. 1997 Nov;273(5 Pt 1):G987-96. [PubMed Link Image]
Target 1 Drug References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  2. Lesclous P, Schramm F, Gallina S, Baroukh B, Guez D, Saffar JL: Histamine mediates osteoclastic resorption only during the acute phase of bone loss in ovariectomized rats. Exp Physiol. 2006 May;91(3):561-70. Epub 2006 Mar 2. [PubMed Link Image]
  3. Kesiova M, Alexandrova A, Yordanova N, Kirkova M, Todorov S: Effects of diphenhydramine and famotidine on lipid peroxidation and activities of antioxidant enzymes in different rat tissues. Pharmacol Rep. 2006 Mar-Apr;58(2):221-8. [PubMed Link Image]
  4. Fukushima K, Aoi Y, Kato S, Takeuchi K: Gastro-protective action of lafutidine mediated by capsaicin-sensitive afferent neurons without interaction with TRPV1 and involvement of endogenous prostaglandins. World J Gastroenterol. 2006 May 21;12(19):3031-7. [PubMed Link Image]
  5. Takahashi HK, Watanabe T, Yokoyama A, Iwagaki H, Yoshino T, Tanaka N, Nishibori M: Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol. 2006 Aug;70(2):450-3. Epub 2006 May 24. [PubMed Link Image]
  6. Fukuda M, Tanaka S, Suzuki S, Kusama K, Kaneko T, Sakashita H: Cimetidine induces apoptosis of human salivary gland tumor cells. Oncol Rep. 2007 Mar;17(3):673-8. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.