| 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 |
|
| Name |
Famotidine |
| Drug Type |
|
| Description |
A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion. [PubChem] |
| Synonyms |
- Famotidina [Spanish]
- Famotidinum [Latin]
|
| Brand Names |
- 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
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide |
| Chemical Formula |
C8H15N7O2S3 |
| Chemical 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  |
| KEGG Compound |
Not Available |
| PubChem Compound |
3325  |
| PubChem Substance |
191368  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA449586  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02242327  |
| RxList Link |
http://www.rxlist.com/cgi/generic/famot.htm  |
| PDRhealth Link |
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pep1325.shtml  |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Famotidine  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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 |
|
| 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  |
| Contraindications |
Show  |
| Interactions |
Show  |
| 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  |
|
|
| General References |
- Drugs.com

- Wikipedia

- RxList

- PDRhealth

|
| Organisms Affected |
|
| Phase 1 Metabolizing Enzymes |
- Cytochrome P450 2C19 (CYP2C19)
|
| Targets |
- Histamine H2 receptor
|
|
Drug Target 1
[top]
|
| Target 1 ID |
124 |
| Target 1 Name |
Histamine H2 receptor |
| Target 1 Synonyms |
- Gastric receptor I
- 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 |
|
| 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  |
| Target 1 UniProtKB/Swiss-Prot ID |
P25021  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
HRH2_HUMAN  |
| 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  |
| Target 1 GenAtlas ID |
HRH2  |
| Target 1 HGNC ID |
HGNC:5183  |
| Target 1 Chromosome Location |
5 |
| Target 1 Locus |
5q35.2 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- 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
]
- 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
]
- 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
]
- Del Valle J, Gantz I: Novel insights into histamine H2 receptor biology. Am J Physiol. 1997 Nov;273(5 Pt 1):G987-96. [PubMed
]
|
| Target 1 Drug References |
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
|