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Record Information
Version3.6
Creation Date2006-05-18 08:25:34 UTC
Update Date2013-02-09 00:11:00 UTC
HMDB IDHMDB01919
Secondary Accession NumbersNone
Metabolite Identification
Common NameFamotidine
DescriptionFamotidine is a histamine H2-receptor antagonist that inhibits stomach acid production, and is commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD/GORD). It is commonly marketed by Merck under the trade names Pepcidine and Pepcid.
Structure
Thumb
Synonyms
  1. Gastridan
  2. Panalba
  3. Tamin
  4. Amfamox
  5. Antodine
  6. Apo-Famotidine
  7. Apogastine
  8. Bestidine
  9. Blocacid
  10. Brolin
  11. Cepal
  12. Confobos
  13. Cronol
  14. Cuantin
  15. Famocid
  16. Famodar
  17. Famodil
  18. Famodin
  19. Famodine
  20. Famogard
  21. Famonit
  22. Famopsin
  23. Famos
  24. Famosan
  25. Famotal
  26. Famotep
  27. Famotidina
  28. Famotidine
  29. Famotidinum
  30. Famotin
  31. Famovane
  32. Famowal
  33. Gastridin
  34. Gastrion
  35. Gastro
  36. Gastrodomina
  37. Gastrofam
  38. Gastropen
  39. Gastrosidin
  40. Hacip
  41. Huberdina
  42. Ingastri
  43. Invigan
  44. Lecedil
  45. Logos
  46. Mensoma
  47. Midefam
  48. Mosul
  49. Motiax
  50. Muclox
  51. Mylanta AR
  52. Neocidine
  53. Nevofam
  54. Notidin
  55. Novo-Famotidine
  56. Nulceran
  57. Nulcerin
  58. Pepcid
  59. Pepcidin
  60. Pepcidin Pepcidine
  61. Pepdine
  62. Pepdul
  63. Pepfamin
  64. Peptan
  65. Peptidin
  66. Purifam
  67. Quamatel
  68. Quamtel
  69. Renapepsa
  70. Restadin
  71. Rogasti
  72. Rubacina
  73. Tipodex
  74. Topcid
  75. Ulcatif
  76. Ulceprax
  77. Ulcofam
  78. Ulfagel
  79. Ulfam
  80. Ulfamid
  81. Ulfinol
  82. Ulgarine
  83. Vagostal
Chemical FormulaC8H15N7O2S3
Average Molecular Weight337.445
Monoisotopic Molecular Weight337.044934829
IUPAC Name3-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}-N-sulfamoylpropanimidamide
Traditional Name3-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}-N-sulfamoylpropanimidamide
CAS Registry Number76824-35-6
SMILES
NC(=N)NC1=NC(CSCCC(=N)NS(N)(=O)=O)=CS1
InChI Identifier
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)
InChI KeyXUFQPHANEAPEMJ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassOrganic Sulfuric Acids and Derivatives
Sub ClassOrganic Sulfuric Acid Diamides
Other Descriptors
  • 1,3-thiazole(ChEBI)
  • Aromatic Heteromonocyclic Compounds
  • guanidines(ChEBI)
  • sulfonamide(ChEBI)
Substituents
  • Guanidine
  • Imine
  • Thiazole
  • Thioether
Direct ParentOrganic Sulfuric Acid Diamides
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.0 mg/mL at 20 °CNot Available
LogP-0.64ISLAM,MS & NARURKAR,MM (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.11ALOGPS
logP-0.25ALOGPS
logP-1.4ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.38ChemAxon
pKa (Strongest Basic)7.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area170.83 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.01 m3·mol-1ChemAxon
Polarizability31.71 Å3ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.0 (0.30-9.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022737
KNApSAcK IDNot Available
Chemspider ID3208
KEGG Compound IDC00025
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFamotidine
NuGOwiki LinkHMDB01919
Metagene LinkHMDB01919
METLIN ID2652
PubChem Compound3325
PDB IDNot Available
ChEBI ID4975
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:
ALDH4A1
Uniprot ID:
P30038
Molecular weight:
55117.24
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT2
Uniprot ID:
O94808
Molecular weight:
76929.885
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT1
Uniprot ID:
Q06210
Molecular weight:
78805.81
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
General function:
Involved in transaminase activity
Specific function:
Not Available
Gene Name:
OAT
Uniprot ID:
P04181
Molecular weight:
48534.39
General function:
Involved in glutamate-cysteine ligase activity
Specific function:
Not Available
Gene Name:
GCLC
Uniprot ID:
P48506
Molecular weight:
68629.42
General function:
Involved in N-acetyltransferase activity
Specific function:
Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
Gene Name:
NAGS
Uniprot ID:
Q8N159
Molecular weight:
58155.835
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name:
BCAT2
Uniprot ID:
O15382
Molecular weight:
33776.315
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of the cognate amino acid to the corresponding tRNA in a two-step reaction: the amino acid is first activated by ATP to form a covalent intermediate with AMP and is then transferred to the acceptor end of the cognate tRNA. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma activation and subsequent phosphorylation dissociates from the multisynthetase complex and assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
Gene Name:
EPRS
Uniprot ID:
P07814
Molecular weight:
170589.705
General function:
Involved in asparagine synthase (glutamine-hydrolyzing) activity
Specific function:
Not Available
Gene Name:
ASNS
Uniprot ID:
P08243
Molecular weight:
62167.855
General function:
Involved in oxidoreductase activity
Specific function:
Important for recycling the chief excitatory neurotransmitter, glutamate, during neurotransmission.
Gene Name:
GLUD2
Uniprot ID:
P49448
Molecular weight:
61433.465
General function:
Involved in glutaminase activity
Specific function:
Plays an important role in the regulation of glutamine catabolism. Promotes mitochondrial respiration and increases ATP generation in cells by catalyzing the synthesis of glutamate and alpha-ketoglutarate. Increases cellular anti-oxidant function via NADH and glutathione production. May play a role in preventing tumor proliferation.
Gene Name:
GLS2
Uniprot ID:
Q9UI32
Molecular weight:
66322.225
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen.
Gene Name:
CTPS1
Uniprot ID:
P17812
Molecular weight:
66689.9
General function:
Involved in glutaminase activity
Specific function:
Catalyzes the first reaction in the primary pathway for the renal catabolism of glutamine. Plays a role in maintaining acid-base homeostasis. Regulates the levels of the neurotransmitter glutamate in the brain. Isoform 2 lacks catalytic activity.
Gene Name:
GLS
Uniprot ID:
O94925
Molecular weight:
65459.525
General function:
Involved in catalytic activity
Specific function:
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:
FTCD
Uniprot ID:
O95954
Molecular weight:
58925.93
General function:
Involved in oxidoreductase activity
Specific function:
May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
Gene Name:
GLUD1
Uniprot ID:
P00367
Molecular weight:
61397.315
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD2
Uniprot ID:
Q05329
Molecular weight:
65410.77
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q99259
Molecular weight:
66896.065
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
General function:
Involved in tetrahydrofolylpolyglutamate synthase activity
Specific function:
Catalyzes conversion of folates to polyglutamate derivatives allowing concentration of folate compounds in the cell and the intracellular retention of these cofactors, which are important substrates for most of the folate-dependent enzymes that are involved in one-carbon transfer reactions involved in purine, pyrimidine and amino acid synthesis. Unsubstitued reduced folates are the preferred substrates. Metabolizes methotrexate (MTX) to polyglutamates.
Gene Name:
FPGS
Uniprot ID:
Q05932
Molecular weight:
59173.37
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate. Participates in cellular nitrogen metabolism and also in liver gluconeogenesis starting with precursors transported from skeletal muscles (By similarity).
Gene Name:
GPT
Uniprot ID:
P24298
Molecular weight:
54636.415
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that converts glutamate to glutamate 5-semialdehyde, an intermediate in the biosynthesis of proline, ornithine and arginine.
Gene Name:
ALDH18A1
Uniprot ID:
P54886
Molecular weight:
87088.29
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the cleavage of 5-oxo-L-proline to form L-glutamate coupled to the hydrolysis of ATP to ADP and inorganic phosphate.
Gene Name:
OPLAH
Uniprot ID:
O14841
Molecular weight:
137456.195
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
General function:
Involved in catalytic activity
Specific function:
Decarboxylates L-arginine to agmatine. Truncated splice isoforms probably lack activity.
Gene Name:
ADC
Uniprot ID:
Q96A70
Molecular weight:
49979.185
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in NAD+ synthase (glutamine-hydrolyzing) activity
Specific function:
Not Available
Gene Name:
NADSYN1
Uniprot ID:
Q6IA69
Molecular weight:
79283.945
General function:
Involved in hydrolase activity
Specific function:
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:
CAD
Uniprot ID:
P27708
Molecular weight:
242981.73
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate.
Gene Name:
GPT2
Uniprot ID:
Q8TD30
Molecular weight:
46982.6
General function:
Involved in CTP synthase activity
Specific function:
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen. Constitutes the rate-limiting enzyme in the synthesis of cytosine nucleotides.
Gene Name:
CTPS2
Uniprot ID:
Q9NRF8
Molecular weight:
65677.005
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
General function:
Involved in glutamate-ammonia ligase activity
Specific function:
ATP + L-glutamate + NH(3) = ADP + phosphate + L-glutamine
Gene Name:
PIG59
Uniprot ID:
A8YXX4
Molecular weight:
42064.1
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of glutamate to tRNA(Glu) in a two-step reaction: glutamate is first activated by ATP to form Glu-AMP and then transferred to the acceptor end of tRNA(Glu) (By similarity).
Gene Name:
EARS2
Uniprot ID:
Q5JPH6
Molecular weight:
58688.1
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AASS
Uniprot ID:
A4D0W4
Molecular weight:
102130.9
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Not Available
Gene Name:
GGT7
Uniprot ID:
A0PJJ9
Molecular weight:
62565.3
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75