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QuickView for Cimetidine (compound)
PubChem
| Name: | Cimetidine |
|---|---|
| PubChem Compound ID: | 2756 |
| Description: | A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRINS output. It also blocks the activity of CYTOCHROME P-450 which might explain proposals for use in NEOADJUVANT THERAPY. |
| Molecular formula: | C10H16N6S |
| Molecular weight: | 252.34 g/mol |
| Synonyms: |
MLS000069791; 1-Cyano-2-methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]g uanidine; Brumetidina; Metracin; DivK1c_000166; Spectrum_000495; Cimetidine [USAN:BAN:INN:JAN]; KBio2_003543; NCGC00024859-01; Dyspamet.
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MLS000069791; 1-Cyano-2-methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]g uanidine; Brumetidina; Metracin; DivK1c_000166; Spectrum_000495; Cimetidine [USAN:BAN:INN:JAN]; KBio2_003543; NCGC00024859-01; Dyspamet; Acibilin; SKF 92334; KBioGR_001323; SPBio_000884; Cimetag; Gastromet; Lopac-C-4522; NCGC00015240-01; Guanidine, N''-cyano-N-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio] ethyl]-; ZINC04475111; N-Cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine; NSC335308; Cimetum; Prestwick_65; Cimetidinum [INN-Latin]; 1-Cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine; 2-Cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine; AIDS032970; Ulcimet; Tagamet; Guanidine, N-cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio) ethyl)-; CCRIS 3247; AIDS-032970; Acinil; EINECS 257-232-2; Ulcedine; CHEBI:3699; KBio2_000975; D00295; Edalene; Spectrum3_001389; Spectrum2_000782; N''-cyano-N-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine; EU-0100293; Cimetidine (JP15/USP); KBioSS_000975; Guanidine, N-cyano-N'-methyl-N''-[2-[[5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-; Ulcomedina; Spectrum4_000812; Cimetidina [INN-Spanish]; Tametin; Tagamet (TN); Tocris-0902; KBio3_002198; KBio2_006111; HSDB 3917; N-Cyano-N'-methyl-[2-[[[5-methyl-1H-imidazol-4-yl]methyl]thio]ethyl]guanidine; Tratul; NINDS_000166; SMR000038895; Cimetidine; N''-Cyano-N-methyl-N'-[2-[(5-methyl-1H-imidazol-4-yl)methylthio]et hyl]guanidine; Guanidine, N-cyano-N'-methyl-N''-[2-[[ (5-methyl-1H-imidazol-4-yl)methyl]thio] ethyl]-; Guanidine, N''-cyano-N-methyl-N'-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)-; Eureceptor; nchembio732-comp5; NCI60_002936; UPCMLD-DP029:001; Cimal; KBio1_000166; DRG-0150; 51481-61-9; NCGC00091439-01; Ulcomet; 2-cyano-1-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
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DrugBank
Identification
| Name: | Cimetidine |
|---|---|
| Name (isomeric): | DB00501 |
| Drug Type: | small molecule |
| Description: | A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRINS output. It also blocks the activity of CYTOCHROME P-450 which might explain proposals for use in NEOADJUVANT THERAPY. |
| Synonyms: |
Cimetidine A/AB; Cimetidine Hcl
|
| Brand: | Cimetum, Cimetag, Tratul, Tametin, Acibilin, Eureceptor, Tagamet HB 200, Ulcomedina, Acinil, Ulcomet, Edalene, Tagamet HB, Ulcimet, Gastromet, Ulcofalk, Tagamet, Ulcerfen, Cimal, Ulcedine, Ulhys, Dyspamet, Peptol, Ulcedin |
| Category: | Histamine Antagonists, Anti-Ulcer Agents, Enzyme Inhibitors, Adjuvants, Analgesics, Histamine H2 Antagonists |
| CAS number: | 51481-61-9 |
Pharmacology
| Indication: | For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion. |
|---|---|
| Pharmacology: |
Cimetidine is a histamine H2-receptor antagonist. It reduces 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. It is used to treat gastrointestinal disorders such as gastric or duod...
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Cimetidine is a histamine H2-receptor antagonist. It reduces 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. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.
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| Mechanism of Action: | Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. |
| Absorption: | Rapid 60-70% |
| Protein binding: | 15-20% |
| Biotransformation: | Hepatic |
| Route of elimination: | The principal route of excretion of cimetidine is the urine. |
| Half Life: | 2 hours |
| Toxicity: | Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat. |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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| Drug interaction: |
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Targets
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
| UniProt ID: | P25021 | ||||
|---|---|---|---|---|---|
| Gene: | HRH2 | ||||
| Actions: | antagonist | ||||
| References: |
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Enzymes
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen
| UniProt ID: | P05177 | ||
|---|---|---|---|
| Gene: | CYP1A2 | ||
| Actions: | inhibitor | ||
| References: |
|
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
| UniProt ID: | P33261 | ||
|---|---|---|---|
| Gene: | CYP2C19 | ||
| Actions: | inhibitor | ||
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | ||
|---|---|---|---|
| Gene: | CYP3A4 | ||
| Actions: | inhibitor | ||
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P20815 | ||
|---|---|---|---|
| Gene: | CYP3A5 | ||
| Actions: | inhibitor | ||
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P24462 | ||
|---|---|---|---|
| Gene: | CYP3A7 | ||
| Actions: | inhibitor | ||
| References: |
|
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
| UniProt ID: | P10635 | |
|---|---|---|
| Gene: | CYP2D6 | |
| Actions: | inhibitor | |
| References: |
|
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB
| UniProt ID: | P15538 | |
|---|---|---|
| Gene: | CYP11B1 | |
| Actions: | inhibitor | |
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)
| UniProt ID: | P10632 | |
|---|---|---|
| Gene: | CYP2C8 | |
| Actions: | inhibitor | |
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan
| UniProt ID: | P11712 | |
|---|---|---|
| Gene: | CYP2C9 | |
| Actions: | inhibitor | |
| References: |
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Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms
| UniProt ID: | P05181 | |
|---|---|---|
| Gene: | CYP2E1 | |
| Actions: | inhibitor | |
| References: |
|
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds
| UniProt ID: | P31513 | |||
|---|---|---|---|---|
| Gene: | FMO3 | |||
| Actions: | substrate | |||
| References: |
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This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines
| UniProt ID: | Q01740 | ||
|---|---|---|---|
| Gene: | FMO1 | ||
| Actions: | substrate | ||
| References: |
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Transporters
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
| UniProt ID: | P08183 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | ABCB1 | ||||||
| Actions: | substrate, inhibitor, inducer | ||||||
| References: |
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Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
| UniProt ID: | O15244 | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Gene: | SLC22A2 | ||||||||
| Actions: | substrate, inhibitor | ||||||||
| References: |
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Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
| UniProt ID: | O15245 | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Gene: | SLC22A1 | ||||||||
| Actions: | substrate, inhibitor | ||||||||
| References: |
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Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
| UniProt ID: | O75751 | ||||
|---|---|---|---|---|---|
| Gene: | SLC22A3 | ||||
| Actions: | substrate, inhibitor | ||||
| References: |
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Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3
| UniProt ID: | O76082 | |||
|---|---|---|---|---|
| Gene: | SLC22A5 | |||
| Actions: | inhibitor | |||
| References: |
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Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
| UniProt ID: | O95342 | |
|---|---|---|
| Gene: | ABCB11 | |
| Actions: | inhibitor | |
| References: |
|
| UniProt ID: | Q4U2R8 | ||||
|---|---|---|---|---|---|
| Gene: | SLC22A6 | ||||
| Actions: | substrate, inhibitor | ||||
| References: |
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Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)
| UniProt ID: | Q8TCC7 | |||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Gene: | SLC22A8 | |||||||||||
| Actions: | substrate, inhibitor | |||||||||||
| References: |
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Solute transporter for tetraethylammonium (TEA), 1- methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acyclovir, ganciclovir and also the zwitterionic cephalosporin, cephalexin and cephradin. Seems to also play a role in the uptake of oxaliplatin (a new platinum anticancer agent). Able to transport paraquat (PQ or N,N-dimethyl-4-4'-bipiridinium); a widely used herbicid. Responsible for the secretion of cationic drugs across the brush border membranes
| UniProt ID: | Q96FL8 | |
|---|---|---|
| Gene: | SLC47A1 | |
| Actions: | inhibitor | |
| References: |
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Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
| UniProt ID: | Q9H015 | ||
|---|---|---|---|
| Gene: | SLC22A4 | ||
| Actions: | inhibitor | ||
| References: |
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Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
| UniProt ID: | Q9NSA0 | |
|---|---|---|
| Gene: | SLC22A11 | |
| Actions: | inhibitor | |
| References: |
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Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
| UniProt ID: | Q9Y694 | ||
|---|---|---|---|
| Gene: | SLC22A7 | ||
| Actions: | substrate, inhibitor | ||
| References: |
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