Gastro
Basic information
- CAS
76824-35-6- Standard SMILES
NC(N)=Nc1nc(CSCCC(N)=NS(N)(=O)=O)cs1- InChIKey
XUFQPHANEAPEMJ-UHFFFAOYSA-N- Molecular formula
- C8H15N7O2S3
- Average molar mass
- 337.5 g/mol
- Monoisotopic mass
- 337.04493627
Overview
Famotidine is a member of guanidines, a sulfonamide and a member of 1,3-thiazoles. It has a role as a H2-receptor antagonist, an anti-ulcer drug and a P450 inhibitor.
Names & identifiers
- Preferred name
- Gastro
- IUPAC
- 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide
- English name
- Famotidine
- Molecular formula
- C8H15N7O2S3
- Molecular weight
- 337.45
Names & synonyms
FamogardFamopsinFamovaneMensomaNevofamPurifamBrolinHacipGastroFamotidine-13C3ApogastineGastrodomina
Show more names
pepdinepepcidIfadaganormk208gastermotiaxmucloxpepdulpeptan
GastrosidinAntodineBestidineBlocacidConfobosCuantinDispronilFamocid
Database identifiers
- CAS
76824-35-6- PubChem CID
- 3325
- DTXSID
DTXSID5023039- ChEBI
CHEBI:4975
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 238 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 469
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Gastric and Ulcer Drugs
Pharmaceuticals
LogP
-0.64
-0.56
Solubility1.0 mg/mL at 20 °C
Melting Point163.5 °C
Physical DescriptionSolid
Collision Cross Section
174.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5023039]
171.05 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
165.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 163 · 163-164°C
- Boiling point
- 562.7 · 562.7±60.0 °C(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 2
- rtecs
- UA2300000
- hs_code
- 29341000
- Toxicity
- LD50 i.v. in mice: 244.4 mg/kg (Yasufumi)
- risk_code
- 20/21/22-45-61
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T
- safety_code
- 22-24/25-53-45-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H303
- Precautionary statements
- P270-P301+P312-P403-P501c
- Hazardous Substances Data
- 76824-35-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Protein BindingThe protein binding of famotidine is about 15 to 22%.
Pharmacodynamics
Famotidine decreases the production of gastric acid, suppresses acid concentration and pepsin content, and decreases the volume of gastric secretion. Famotidine inhibits both basal and nocturnal gastric acid secretion, as well as acid secretion stimulated by food, caffeine, insulin, and pentagastrin. Famotidine has a dose-dependent therapeutic action, with the highest dose having the most extended duration of action and the highest inhibitory effect on gastric acid secretion. Following oral administration, the onset of action is within one hour, and the peak effect is reached within 1-3 hours. The duration of effect is about 10-12 hours.
Mechanism of Action
Histamine acts as a local hormone that stimulates the acid output by parietal cells via a paracrine mechanism. Neuroendocrine cells called enterochromaffin-like (ECL) cells lie close to the parietal cells and regulate the basal secretion of histamine. Histamine release is also promoted from stimulation by acetylcholine and gastrin, a peptide hormone. Gastrin (G) cells release gastrin, which works on CCK<sub>2</sub> receptors on ECL cells. This action promotes the release of histamine from ECL cells. Upon release, histamine acts on H<sub>2</sub> receptors expressed on the basolateral membrane of parietal cells, leading to increased intracellular cAMP levels and activated proton pumps on parietal cells. Proton pump releases more protons into the stomach, thereby increasing the secretion of acid. In conditions that are associated with acid hypersecretion such as ulcers, there is a loss of regulation of acid secretion. Famotidine works on H<sub>2</sub> receptors and blocks the actions of histamine.
Biological Half-LifeThe elimination half-life is about 2 to 4 hours. The half-life is expected to increase nonlinearly in patients with decreased renal function.
Metabolism/MetabolitesFamotidine undergoes minimal first-pass metabolism. About 25-30% of the drug is eliminated through hepatic metabolism. The only metabolite identified in humans is the S-oxide.
Related reactions
1 records
Compound notes
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