Tìm theo
Tamoxifen
Các tên gọi khác (25 ) :
  • (Z)-2-(4-(1,2-Diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamine
  • (Z)-2-(Para-(1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylamine
  • 1-P-beta-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • 1-Para-beta-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • Apo-tamox
  • Citofen
  • Crisafeno
  • Diemon
  • Gen-tamoxifen
  • Istubol
  • Noltam
  • Nourytam
  • Oncomox
  • Retaxim
  • Tamofen
  • Tamone
  • Tamoxasta
  • Tamoxifen
  • Tamoxifène
  • Tamoxifene
  • Tamoxifeno
  • Tamoxifenum
  • trans-Tamoxifen
  • Valodex
  • Zemide
Thuốc chống ung thư và tác động vào hệ thống miễn dịch
Thuốc Gốc
Small Molecule
CAS: 10540-29-1
ATC: L02BA01
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C26H29NO
PTK: 371.5146
One of the selective estrogen receptor modulators (SERM) with tissue-specific activities for the treatment and prevention of estrogen receptor positive breast cancer. Tamoxifen acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism, bone density, and cell proliferation in the endometrium. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C26H29NO
Phân tử khối
371.5146
Monoisotopic mass
371.224914555
InChI
InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI Key
InChIKey=NKANXQFJJICGDU-QPLCGJKRSA-N
IUPAC Name
(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine
Traditional IUPAC Name
tamoxifen
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1
Độ tan chảy
97 °C
Độ hòa tan
0.000167 mg/mL at 25 °C
logP
7.1
logS
-5.6
pKa (Strongest Basic)
8.76
PSA
12.47 Å2
Refractivity
128.43 m3·mol-1
Polarizability
44.19 Å3
Rotatable Bond Count
8
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
3
Bioavailability
1
MDDR-Like Rule
true
Dược Lực Học : Tamoxifen belongs to a class of drugs called selective estrogen receptor modulators (SERMs), which have both estrogenic and antiestrogenic effects. Tamoxifen has the same nucleus as diethylstilbestrol but possesses an additional side chain (trans isomer) which accounts for its antiestrogenic activity.
Cơ Chế Tác Dụng : One of the selective estrogen receptor modulators (SERM) with tissue-specific activities for the treatment and prevention of estrogen receptor positive breast cancer. Tamoxifen acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism, bone density, and cell proliferation in the endometrium. [PubChem] Tamoxifen is a nonsteroidal agent that binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes. The prolonged binding of tamoxifen to the nuclear chromatin of these results in reduced DNA polymerase activity, impaired thymidine utilization, blockade of estradiol uptake, and decreased estrogen response. It is likely that tamoxifen interacts with other coactivators or corepressors in the tissue and binds with different estrogen receptors, ER-alpha or ER-beta, producing both estrogenic and antiestrogenic effects.
Dược Động Học :
▧ Absorption :
When a single oral dose of 20 mg is given, the average peak plasma concentration (Cmax) is 40 ng/mL which occurred approximately 5 hours after dosing (Tmax). The Cmax of N-desmethyl tamoxifen is 15 ng/mL. Steady-state concentrations for tamoxifen is achieved in 4 weeks, while steady-state concentrations for N-desmethyl tamoxifen is achieved in 8 weeks.
▧ Metabolism :
Hepatic. Tamoxifen is extensively metabolized after oral administration. N-Desmethyl-tamoxifen is the major metabolite found in plasma. N-Desmethyl-tamoxifen's activity is similar to tamoxifen. 4-hydroxy-tamoxifen and a side chain primary alcohol derivative of tamoxifen have been identified as minor metabolites in plasma. 4-Hydroxy-tamoxifen formation is catalyzed mainly by cytochrome P450 (CYP) 2D6, and also by CYP2C9 and 3A4. At high tamoxifen concentrations, CYP2B6 also catalyzes 4-hydroxylation of the parent drug. 4-Hydroxy-tamoxifen possesses 30- to 100-times greater affinity for the estrogen receptor and 30- to 100-times greater potency at inhibiting estrogen-dependent cell proliferation compared to tamoxifen. It is also metabolized by flavin monooxygenases FMO1 and FMO3 to form tamoxifen-N-oxide.
▧ Route of Elimination :
65% of the dose was excreted from the body over 2 weeks in which fecal excretion was the primary route of elimination. Tamoxifen is excreted mainly as polar conjugates, with unchanged drug and unconjugated metabolites accounting for less than 30% of the total fecal radioactivity.
▧ Half Life :
The decline in tamoxifen plasma concentrations is biphasic with a terminal elimination half-life of approximately 5 to 7 days. The estimated half-life of N-desmethyl tamoxifen is 14 days.
▧ Clearance :
Clearance (CL/F) as body weight adjusted in female pediatric patients was approximately 2.3-fold higher than in female breast cancer patients.
Độc Tính : Signs observed at the highest doses following studies to determine LD50 in animals were respiratory difficulties and convulsions.
Chỉ Định : Tamoxifen is indicated for the treatment of metastatic breast cancer in women and men and ductal carcinoma in Situ.
Tương Tác Thuốc :
  • Acenocoumarol Tamoxifen may increase the serum concentration of Acenocoumarol increasing the risk of bleeding. Concomitant therapy should be avoided.
  • Aminoglutethimide Aminoglutethimide may increase Tamoxifen clearance decreasing its therapeutic effect. Consider alternate therapy or monitor for changes in Tamoxifen effects when Aminoglutethimide is initiated, discontinued or dose changed.
  • Amiodarone Amiodarone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Amprenavir Amprenavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Atazanavir Atazanavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Capecitabine Capecitabine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Capecitabine is initiated, discontinued or dose changed.
  • Chloroquine Chloroquine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Chlorpromazine Chlorpromazine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Cimetidine Cimetidine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Cinacalcet Cinacalcet may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Clarithromycin Clarithromycin may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Clomipramine Clomipramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Clozapine Clozapine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Cocaine Cocaine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Conivaptan Conivaptan may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Darifenacin Darifenacin may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Darunavir Darunavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Delavirdine Delavirdine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Desipramine Desipramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Diphenhydramine Diphenhydramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Duloxetine Duloxetine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Floxuridine Floxuridine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Floxiridine is initiated, discontinued or dose changed.
  • Fluconazole Fluconzole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Fluconazole is initiated, discontinued or dose changed.
  • Fluorouracil Fluorouracil may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Fluorouracil is initiated, discontinued or dose changed.
  • Fluoxetine Fluoxetine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Flurbiprofen Flurbiprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Flurbiprofen is initiated, discontinued or dose changed.
  • Fosamprenavir Fosmprenavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Gemfibrozil Gemfibrozil may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Gemfibrozil is initiated, discontinued or dose changed.
  • Haloperidol Haloperidol may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Ibuprofen Ibuprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Ibuprofen is initiated, discontinued or dose changed.
  • Imatinib Imatinib may increase the serum concentration of Tamoxifen by decreasing its metabolism and clearance. Imatinib may also decrease the therapeutic effect of Tamoxifen by decreasing active metabolite production. Monitor for changes in the therapeutic/adverse effects of Tamoxifen if Imatinib is initiated, discontinued or dose changed.
  • Imipramine Imipramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Indinavir Indinavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Indomethacin Indomethacin may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Indomethacin is initiated, discontinued or dose changed.
  • Isoniazid Isoniazid may increase the serum concentration of Tamoxifen by decreasing its metabolism and clearance. Isoniazid may also decrease the therapeutic effect of Tamoxifen by decreasing active metabolite production. Monitor for changes in the therapeutic/adverse effects of Tamoxifen if Isoniazid is initiated, discontinued or dose changed.
  • Itraconazole Itraconazole may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Ketoconazole Ketoconazole may increase the serum concentration of Tamoxifen by decreasing its metabolism and clearance. Ketoconazole may also decrease the therapeutic effect of Tamoxifen by decreasing active metabolite production. Monitor for changes in the therapeutic/adverse effects of Tamoxifen if Ketoconazole is initiated, discontinued or dose changed.
  • Lidocaine Lidocaine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Lopinavir Lopinavir may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Lumefantrine Lumefantrine, a moderate CYP2D6 inhibitor, may decrease the formation of highly potent tamoxifen metabolites. Concomitant therapy may decrease the effectiveness of tamoxifen. Consider alternate therapy.
  • Mefenamic acid Mefenamic acid may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Mefenamic acid is initiated, discontinued or dose changed.
  • Methadone Methadone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Methimazole Methimazole may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Miconazole Miconazole may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Nefazodone Nefazodone may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Nelfinavir Nelfinavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Nicardipine Nicardipine may increase the serum concentration of Tamoxifen by decreasing its metabolism and clearance. Nicardipine may also decrease the therapeutic effect of Tamoxifen by decreasing active metabolite production. Monitor for changes in the therapeutic/adverse effects of Tamoxifen if Nicardipine is initiated, discontinued or dose changed.
  • Nilotinib Nilotinib may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Paroxetine Paroxetine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Pergolide Pergolide may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Pioglitazone Pioglitazone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Piroxicam Piroxicam may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Piroxicam is initiated, discontinued or dose changed.
  • Posaconazole Posaconazole may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Pyrimethamine Pyrimethamine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Quinidine Quinidine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Quinine Quinine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Quinupristin This combination presents an increased risk of toxicity
  • Ranolazine Ranolazine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Rifabutin The rifamycin decreases the effect of anti-estrogen
  • Rifampicin The rifamycin decreases the effect of anti-estrogen
  • Ritonavir Ritonavir may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Rivaroxaban Tamoxifen may increase serum concentrations of Rivaroxaban increasing the risk of bleeding. Concomitant therapy should be avoided.
  • Saquinavir Saquinavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Sertraline Sertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Sitaxentan Sitaxsentan may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sitaxsentan is initiated, discontinued or dose changed.
  • Sulfadiazine Sulfadiazine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfadiazine is initiated, discontinued or dose changed.
  • Sulfisoxazole Sulfisoxazole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfisoxazole is initiated, discontinued or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Tamoxifen. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tamoxifen if Telithromycin is initiated, discontinued or dose changed.
  • Terbinafine Terbinafine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Thioridazine Thioridazine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Ticlopidine Ticlopidine may decrease the therapeutic effect of tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tolbutamide Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tamoxifen. Consider alternate therapy or monitor for changes in Tamoxifen therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
  • Topotecan The p-glycoprotein inhibitor, Tamoxifen, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
  • Tranylcypromine The CYP2D6 inhibitor, Tranylcypromine, may decrease the efficacy of Tamoxifen by reducing active metabolite production. Consider alternate therapy.
  • Trazodone Trazodone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tretinoin The moderate CYP2C8 inhibitor, Tamoxifen, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Tamoxifen is initiated, discontinued to dose changed.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of tamoxifen by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of tamoxifen if voriconazole is initiated, discontinued or dose changed.
  • Warfarin Tamoxifen, a CYP2C9 inhibitor, may increase the serum concentration of warfarin by decreasing its metabolism. Concomitant therapy is contraindicated due to significant increase in bleed risk.
Liều Lượng & Cách Dùng : Solution - Oral - 10 mg/5 mL
Tablet - Oral - 10 mg, 20 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Medicamerc
    Sản phẩm biệt dược : Adifen
  • Công ty : Sawai Seiyaku
    Sản phẩm biệt dược : Adopan
  • Công ty : Teva Int'l
    Sản phẩm biệt dược : Bilem
  • Công ty : Cadila
    Sản phẩm biệt dược : Caditam
  • Công ty :
    Sản phẩm biệt dược : Citofen
  • Công ty : LKM
    Sản phẩm biệt dược : Crisafeno
  • Công ty : Docpharma
    Sản phẩm biệt dược : Doctamoxifene
  • Công ty : Ebewe
    Sản phẩm biệt dược : Ebefen
  • Công ty : Sandoz
    Sản phẩm biệt dược : Fenahex
  • Công ty : Merck Serono
    Sản phẩm biệt dược : Genox
  • Công ty : Biogalenic
    Sản phẩm biệt dược : Gynatam
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Istubal
  • Sản phẩm biệt dược : Mammonex
  • Công ty : Aspen Pharmacare
    Sản phẩm biệt dược : Neophedan
  • Công ty :
    Sản phẩm biệt dược : Noltam
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Nolvadex
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Nolvadex-D
  • Công ty : Remedica
    Sản phẩm biệt dược : Novofen
  • Công ty : Sun
    Sản phẩm biệt dược : Oncomox
  • Công ty : Pharmascience
    Sản phẩm biệt dược : PMS-Tamoxifen
  • Sản phẩm biệt dược : Soltamox
  • Công ty : Orion
    Sản phẩm biệt dược : Tadex
  • Công ty : Medochemie
    Sản phẩm biệt dược : Tamifen
  • Công ty : Mithra
    Sản phẩm biệt dược : Tamizam
  • Công ty : Sanofi-Aventis
    Sản phẩm biệt dược : Tamofen
  • Công ty : Actavis
    Sản phẩm biệt dược : Tamoneprin
  • Công ty : Pharmachemie
    Sản phẩm biệt dược : Tamoplex
  • Công ty : Ascent
    Sản phẩm biệt dược : Tamoxen
  • Công ty : Celon
    Sản phẩm biệt dược : Tamoxilon
  • Công ty : Hetero
    Sản phẩm biệt dược : Tamtero
  • Công ty : Zodiac
    Sản phẩm biệt dược : Tecnotax
  • Công ty : Alkem
    Sản phẩm biệt dược : Tomifen
  • Công ty :
    Sản phẩm biệt dược : Valodex
  • Công ty :
    Sản phẩm biệt dược : Zemide
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00675
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2733526
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505515
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07108
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00966
ChemSpider
http://www.chemspider.com/Chemical-Structure.2015313.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=20607
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-0144-91
PharmGKB
http://www.pharmgkb.org/drug/PA451581
Wikipedia
http://en.wikipedia.org/wiki/Tamoxifen
RxList
http://www.rxlist.com/cgi/generic/tamox.htm
Drugs.com
http://www.drugs.com/tamoxifen.html
... loading
... loading