Tìm theo
Cimetidine
Các tên gọi khác (11 ) :
  • 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
  • Cimetag
  • Cimetidin
  • Cimetidina
  • Cimétidine
  • Cimetidinum
  • N-Cyano-n'-methyl-n''-(2-([(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine
  • N''-cyano-N-methyl-n'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]thio}ethyl)guanidine
  • Tagamet hb 200
  • Ulcerfen
Thuốc đường tiêu hóa
Thuốc Gốc
Small Molecule
CAS: 51481-61-9
ATC: A02BA01
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C10H16N6S
PTK: 252.339
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. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H16N6S
Phân tử khối
252.339
Monoisotopic mass
252.115715232
InChI
InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
InChI Key
InChIKey=AQIXAKUUQRKLND-UHFFFAOYSA-N
IUPAC Name
(Z)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
Traditional IUPAC Name
cimetidine
SMILES
C\N=C(\NCCSCC1=C(C)NC=N1)NC#N
Độ tan chảy
142 °C
Độ hòa tan
9380 mg/L (at 25 °C)
logP
0.40
logS
-1.35
pKa (strongest acidic)
13.38
pKa (Strongest Basic)
6.91
PSA
88.89 Å2
Refractivity
70.32 m3·mol-1
Polarizability
27.47 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
5
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-5.89
pKa
6.8
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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. [PubChem] 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.
Dược Động Học :
▧ Absorption :
Rapid 60-70%
▧ Protein binding :
15-20%
▧ Metabolism :
Hepatic
▧ Route of Elimination :
The principal route of excretion of cimetidine is the urine.
▧ Half Life :
2 hours
Độc Tính : Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.
Chỉ Định : For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
Tương Tác Thuốc :
  • Acenocoumarol Cimetidine may increase the anticoagulant effect of acenocoumarol.
  • Alfentanil Increases the effect of the narcotic
  • Alprazolam Cimetidine may increase the effect of the benzodiazepine, alprazolam.
  • Aminophylline Cimetidine may increase the serum concentration of aminophylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of aminophylline if cimetidine is initiated, discontinued or dose changed.
  • Amitriptyline Cimetidine may increase the effect of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if cimetidine is initiated, discontinued or dose changed.
  • Amoxapine Cimetidine may increase the effect of the tricyclic antidepressant, amoxapine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amoxapine if cimetidine is initiated, discontinued or dose changed.
  • Anisindione Cimetidine may increase the anticoagulant effect of anisindione.
  • Astemizole Increased risk of cardiotoxicity and arrhythmias
  • Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
  • Bendamustine CA1A2 hepatic enzyme metabolism is affected by increased amounts of bendamustine by cimetidine. In addition, decreased conversion of bendamustine to active metabolites occurs. Amounts of active metabolites may be decreased. Decreased conversion of bendamustine to active metabolites also occurs.
  • Bromazepam Co-administration with cimetidine will cause a reduction in bromazepam clearance and increases half-life.
  • Carbamazepine Cimetidine may increase the serum concentration of carbamazepine during the first few days of concomitant therapy. Monitor for changes in the therapeutic and adverse effects of carbamazepine if cimetidine is initiated, discontinued or dose changed.
  • Carmustine Increases myelosuppression caused by carmustine
  • Cefditoren H2-Antagonists such as cimetidine may decrease the serum concentration of cefditoren. Cefditoren prescribing information recommends to avoid concomitant use with H2-antagonists (eg, famotidine, ranitidine) and antacids as well. Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of H2-antagonists can not be avoided.
  • Chlordiazepoxide Cimetidine may increase the effect of the benzodiazepine, chlordiazepoxide.
  • Clomipramine Cimetidine may increase the effect of the tricyclic antidepressant, clomipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of clomipramine if cimetidine is initiated, discontinued or dose changed.
  • Clonazepam Cimetidine may increase the effect of the benzodiazepine, clonazepam.
  • Clorazepate Cimetidine may increase the effect of the benzodiazepine, clorazepate.
  • Clozapine Cimetidine may increase the serum concentratin of clozapine. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of clozapine if cimetidine is initiated, discontinued or dose changed.
  • Codeine Cimetidine may decrease the therapeutic effect of codeine by decreasing its metabolism to its active metabolite, morphine. Monitor for changes in the therapeutic effect of codeine if cimetidine is initiated, discontinued or dose changed.
  • Desipramine Cimetidine may increase the effect of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if cimetidine is initiated, discontinued or dose changed.
  • Dextropropoxyphene Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of propoxyphene. Monitor for changes in the therapeutic and adverse effects of propoxyphene if cimetidine is intitiated, discontinued or dose changed.
  • Diazepam Cimetidine may increase the effect of the benzodiazepine, diazepam.
  • Dicoumarol Cimetidine may increase the anticoagulant effect of dicumarol.
  • Dihydroquinidine barbiturate Increases the effect of quinidine
  • Dofetilide Increases effect/toxicity of dofetilide
  • Donepezil Possible antagonism of action
  • Doxepin Cimetidine may increase the effect of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if cimetidine is initiated, discontinued or dose changed.
  • Dyphylline Increases the effect of theophylline
  • Eltrombopag Affects hepatic CYP1A2 metabolism, will decrease effect/level of eltrombopag. Affects hepatic CYP2C9/10 metabolism, will decrease effect/level of eltrombopag.
  • Enoxacin Cimetidine may decrease the absorption of enoxacin.
  • Epirubicin Cimetidine can increase epirubicin levels
  • Estazolam Cimetidine may increase the effect of the benzodiazepine, estazolam.
  • Ethotoin Increases the effect of hydantoin
  • Fentanyl Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of fentanyl. Closely monitor changes in the therapeutic and adverse effects of fentanyl if cimetidine is initiated, discontinued or dose changed.
  • Flecainide Cimetidine, a moderate CYP2D6 inhibitor, may decrease the metabolism of flecainide.
  • Flurazepam Cimetidine may increase the effect of the benzodiazepine, flurazepam.
  • Fosphenytoin Cimetidine may increase the serum concentration of fosphenytoin by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of fosphenytoin if cimetidine is initiated, discontinued or dose changed.
  • Galantamine Possible antagonism of action
  • Halazepam Cimetidine may increase the effect of the benzodiazepine, halazepam.
  • Heroin Cimetidine increases the effect of the narcotic
  • Imipramine Cimetidine may increase the effect of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if cimetidine is initiated, discontinued or dose changed.
  • Itraconazole The H2-receptor antagonist, cimetidine, may decrease the absorption of itraconazole.
  • Ketazolam Cimetidine may increase the effect of the benzodiazepine, ketazolam.
  • Ketoconazole The H2-receptor antagonist, cimetidine, may decrease the absorption of ketoconazole.
  • Labetalol Cimetidine may increase the serum concentration of labetolol by decreasing its metabolism.
  • Lidocaine Increases the effect and toxicity of lidocaine
  • Mephenytoin Increases the effect of hydantoin
  • Metformin Cimetidine may increase the therapeutic and adverse effects of metformin by increasing its serum concentration. Consider alternate therapy.
  • Methadone Cimetidine, a moderate CYP3A4 inhibitor, may increase the serum concentration of metahdone, a CYP3A4 substrate. Monitor for changes in the therapeutic and adverse effects of methadone if cimetidine is initiatied, discontinued or dose changed.
  • Metoprolol Cimetidine may increase the serum concentration of metoprolol by decreasing its metabolism.
  • Midazolam Cimetidine may increase the effect of the benzodiazepine, midazolam.
  • Moclobemide Cimetidine may increase the serum concentration of moclobemide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of moclobemide if cimetidine is initiated, discontinued or dose changed.
  • Nalbuphine Increases the effect of the narcotic
  • Nifedipine Cimetidine may increase the effect of the calcium channel blocker, nifedipine.
  • Nimodipine Cimetidine increases the effect of the calcium channel blocker, nimodipine.
  • Nitrendipine Cimetidine increases the effect of the calcium channel blocker, nitrendipine.
  • Nortriptyline Cimetidine may increase the effect of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if cimetidine is initiated, discontinued or dose changed.
  • Oxtriphylline Cimetidine may increase the serum concentration of oxtriphylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of oxtriphylline if cimetidine is initiated, discontinued or dose changed.
  • Oxycodone Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of oxycodone. Monitor for changes in the therapeutic and adverse effects of oxycodone if cimetidine is initiated, discontinued or dose changed.
  • Oxymorphone Increases the effect of the narcotic
  • Pazopanib Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
  • Phenytoin Cimetidine may increase the therapeutic effect of phenytoin.
  • Posaconazole Significant decrease of posaconazole levels
  • Pramipexole Cimetidine may increase the effect and toxicity of pramipexole.
  • Prazepam Cimetidine may increase the effect of the benzodiazepine, prazepam.
  • Procainamide The histamine H2-receptor antagonist, cimetidine, may increase the effect of procainamide.
  • Propranolol Cimetidine may increase the serum concentration of propranolol by decreasing its metabolism.
  • Protriptyline Cimetidine may increase the effect of tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of trimipramine if cimetidine is initiated, discontinued or dose changed.
  • Quazepam Cimetidine may increase the effect of the benzodiazepine, quazepam.
  • Quinidine Cimetidine may increase the serum concentration of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if cimetidine is initiated, discontinued or dose changed.
  • Quinidine barbiturate Increases the effect of quinidine
  • Rivastigmine Possible antagonism of action
  • Roflumilast Increases roflumilast levels.
  • Sildenafil Increases the effect and toxicity of sildenafil
  • Sufentanil Increases the effect of the narcotic
  • Tacrine The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Cimetidine, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Cimetidine is initiated, discontinued or if the dose is changed.
  • Tacrolimus Cimetidine may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Cimetidine therapy is initiated, discontinued or altered.
  • Tamoxifen Cimetidine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tamsulosin Cimetidine, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Cimetidine is initiated, discontinued, or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Theophylline Cimetidine may increase the effect of theophylline.
  • Ticlopidine Cimetidine may increase Ticlopidine levels. Avoid concomitant therapy.
  • Timolol Cimetidine may increase the serum concentration of timolol by decreasing its metabolism.
  • Tizanidine Cimetidine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
  • Tolazoline Anticipated loss of efficacy of tolazoline
  • Tolterodine Cimetidine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
  • Tramadol Cimetidine may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Cimetidine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trazodone The CYP3A4 inhibitor, Cimetidine, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Cimetidine is initiated, discontinued or dose changed.
  • Triazolam Cimetidine may increase the serum concentration of triazolam by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of triazolam if cimetidine is initiated, discontinued or dose changed.
  • Trimipramine Cimetidine may increase the effect of tricyclic antidepressant, trimipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of trimipramine if cimetidine is initiated, discontinued or dose changed.
  • Vilazodone Cimetidine may decrease the metabolism of Selective Serotonin Reuptake Inhibitors. Consider using an alternative H2-antagonist to avoid the risk of selective serotonin reuptake inhibitor (SSRI) toxicity. Monitor for increased therapeutic or toxic effects of SSRI if cimetidine is initiated/dose increased, or decreased effects if cimetidine is discontinued/dose decreased.
  • Warfarin Cimetidine may increase the serum concentration of warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if cimetidine is initiated, discontinued or dose changed.
  • Zaleplon Cimetidine may increase the serum concentration of zaleplon by decreasing its metabolism. Reduce the initial dose of zaleplon to 5 mg in patients receiving cimetidine.
Liều Lượng & Cách Dùng : Injection - Intravenous - 6 mg/ml
Solution - Oral - 300 mg/5 ml
Solution - Oral - 300 mg/ml
Tablet, film coated - Oral - 200 mg
Tablet, film coated - Oral - 300 mg
Tablet, film coated - Oral - 400 mg
Tablet, film coated - Oral - 800 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Julphar
    Sản phẩm biệt dược : Cimetag
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Tagamet
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Tagamet HB
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Tagamet HB200
  • Công ty :
    Sản phẩm biệt dược : Ulcedine
  • Công ty : Finadiet
    Sản phẩm biệt dược : Ulcerfen
  • Công ty : Farmasa
    Sản phẩm biệt dược : Ulcimet
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00501
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2756
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505360
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00295
ChemSpider
http://www.chemspider.com/Chemical-Structure.2654.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=22889
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0093-8181-01
PharmGKB
http://www.pharmgkb.org/drug/PA449001
Wikipedia
http://en.wikipedia.org/wiki/Cimetidine
RxList
http://www.rxlist.com/cgi/generic/cimet.htm
Drugs.com
http://www.drugs.com/cdi/cimetidine.html
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