Peringatan Keamanan

High doses of tamoxifen in animals lead to respiratory difficulty and convulsions.L7799,L7802 High doses in advanced metastatic cancer patients resulted in acute neurotoxicity seen by tremor, hyperreflexia, unsteady gait, and dizziness.L7799,L7802 Patients experiencing and overdose should be given supportive treatment as no specific treatment for overdose is suggested.L7799,L7802

Tamoxifen

DB00675

small molecule approved

Deskripsi

Tamoxifen is a non-steroidal antiestrogen used to treat estrogen receptor positive breast cancers as well as prevent the incidence of breast cancer in high risk populations.A1025,L7799,L7802 Tamoxifen is used alone or as an adjuvant in these treatments.L7799,L7802 Tamoxifen may no longer be the preferred treatment for these types of cancers as patients generally have better survival, side effect profiles, and compliance with anastrozole.A1026

Tamoxifen was granted FDA approval on 30 December 1977.L7799

Struktur Molekul 2D

Berat 371.5146
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) The terminal elimination half-life of tamoxifen is 5 to 7 days, while the half-life of N-desmethyltamoxifen, the primary circulating metabolite, is approximately 14 days.[L7799,L7802]
Volume Distribusi The volume of distribution of tamoxifen is approximately 50-60L/kg.[A182207]
Klirens (Clearance) The clearance of tamoxifen was 189mL/min in a study of six postmenopausal women.[A182213]

Absorpsi

An oral dose of 20mg reaches a Cmax of 40ng/mL with a Tmax of 5 hours.L7799,L7802 The metabolite N-desmethyltamoxifen reaches a Cmax of 15ng/mL.L7799,L7802 10mg of tamoxifen orally twice daily for 3 months results in a Css of 120ng/mL and a Css of 336ng/mL.L7799,L7802

Metabolisme

Tamoxifen can by hydroxylated to ?-hydroxytamoxifen which is then glucuronidated or undergoes sulfate conjugation by sulfotransferase 2A1.A182102,A182108 Tamoxifen can also undergo N-oxidation by flavin monooxygenases 1 and 3 to tamoxifen N-oxide.A182102,A182108,A182111 Tamoxifen is N-dealkylated to N-desmethyltamoxifen by CYP2D6, CYP1A1, CYP1A2, CYP3A4, CYP1B1, CYP2C9, CYP2C19, and CYP3A5.A14873,A182102,A182105,A182108,A182111 N-desmethyltamoxifen can be sulfate conjugated to form N-desmethyltamoxifen sulfate, 4-hydroxylated by CYP2D6 to form endoxifen, or N-dealkylated again by CYP3A4 and CYP3A5 to N,N-didesmethyltamoxifen.A182102,A182105,A182183 N,N-didesmethyltamoxifen undergoes a substitution reaction to form tamoxifen metabolite Y, followed by ether cleavage to metabolite E, which can then be sulfate conjugated by sulfotransferase 1A1 and 1E1 or O-glucuronidated.A182183,A182249 Tamoxifen can also by 4-hydroxylated by CYP2D6, CYP2B6, CYP3A4, CYP2C9, and CYP2C19 to form 4-hydroxytamoxifen.A14873,A182102,A182105,A182108 4-hydroxytamoxifen can undergo glucuronidation by UGT1A8, UGT1A10, UGT2B7, and UGT2B17 to tamoxifen glucuronides, sulfate conjugation by sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, or N-dealkylation by CYP3A4 and CYP3A5 to endoxifen.A182102,A182105 Endoxifen undergoes demethylation to norendoxifen, a reversible sulfate conjugation reaction via sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, sulfate conjugation via sulfotransferase 2A1 to 4-endoxifen sulfate, or glucuronidation via UGT1A8, UGT1A10, UGT2B7, or UGT2B15 to tamoxifen glucuronides.A182183,A182102,A182105

Rute Eliminasi

Tamoxifen is mainly eliminated in the feces.L7799,L7802 Animal studies have shown 75% of radiolabelled tamoxifen recovered in the feces, with negligible collection from urine.A182201 However, 1 human study showed 26.7% recovery in the urine and 24.7% in the feces.A182204

Farmakogenomik

2 Varian
CYP2D6 (rs3892097)

Patients with this genotype have reduced metabolism of tamoxifen resulting in reduced plasma concentrations its active form endoxifen.

F5 (rs6025)

Patients with this genotype have increased risk of a thromboembolic event with tamoxifen.

Interaksi Makanan

3 Data
  • 1. Exercise caution with St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce the serum concentration of tamoxifen.
  • 2. Take with a full glass of water.
  • 3. Take with or without food.

Interaksi Obat

1475 Data
Afatinib The serum concentration of Afatinib can be increased when it is combined with Tamoxifen.
Bosutinib The serum concentration of Bosutinib can be increased when it is combined with Tamoxifen.
Brentuximab vedotin The serum concentration of Brentuximab vedotin can be increased when it is combined with Tamoxifen.
Glycochenodeoxycholic Acid Tamoxifen may decrease the excretion rate of Glycochenodeoxycholic Acid which could result in a higher serum level.
Pravastatin Tamoxifen may decrease the excretion rate of Pravastatin which could result in a higher serum level.
Loratadine Tamoxifen may decrease the excretion rate of Loratadine which could result in a higher serum level.
Atropine Tamoxifen may decrease the excretion rate of Atropine which could result in a higher serum level.
Fluorescein Tamoxifen may decrease the excretion rate of Fluorescein which could result in a higher serum level.
Cefaclor Tamoxifen may decrease the excretion rate of Cefaclor which could result in a higher serum level.
Tinidazole Tamoxifen may decrease the excretion rate of Tinidazole which could result in a higher serum level.
Repaglinide Tamoxifen may decrease the excretion rate of Repaglinide which could result in a higher serum level.
Ezetimibe Tamoxifen may decrease the excretion rate of Ezetimibe which could result in a higher serum level.
Taurocholic acid Tamoxifen may decrease the excretion rate of Taurocholic acid which could result in a higher serum level.
Indocyanine green acid form Tamoxifen may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
Pilsicainide Tamoxifen may decrease the excretion rate of Pilsicainide which could result in a higher serum level.
Glycyrrhizic acid Tamoxifen may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
Belantamab mafodotin Tamoxifen may decrease the excretion rate of Belantamab mafodotin which could result in a higher serum level.
Ursodeoxycholic acid Tamoxifen may decrease the excretion rate of Ursodeoxycholic acid which could result in a higher serum level.
Edoxaban The serum concentration of Edoxaban can be increased when it is combined with Tamoxifen.
Ledipasvir The serum concentration of Ledipasvir can be increased when it is combined with Tamoxifen.
Naloxegol The serum concentration of Naloxegol can be increased when it is combined with Tamoxifen.
Pazopanib The serum concentration of Pazopanib can be increased when it is combined with Tamoxifen.
Prucalopride The serum concentration of Prucalopride can be increased when it is combined with Tamoxifen.
Silodosin The excretion of Silodosin can be decreased when combined with Tamoxifen.
Topotecan The serum concentration of Topotecan can be increased when it is combined with Tamoxifen.
Aripiprazole The metabolism of Aripiprazole can be increased when combined with Tamoxifen.
Aripiprazole lauroxil The metabolism of Aripiprazole lauroxil can be increased when combined with Tamoxifen.
Deferasirox The serum concentration of Tamoxifen can be increased when it is combined with Deferasirox.
Peginterferon alfa-2b The serum concentration of Tamoxifen can be increased when it is combined with Peginterferon alfa-2b.
Teriflunomide The serum concentration of Tamoxifen can be decreased when it is combined with Teriflunomide.
Leflunomide The serum concentration of Tamoxifen can be decreased when it is combined with Leflunomide.
Dabrafenib The serum concentration of Tamoxifen can be decreased when it is combined with Dabrafenib.
Eliglustat The metabolism of Eliglustat can be decreased when combined with Tamoxifen.
Ibrutinib The metabolism of Ibrutinib can be decreased when combined with Tamoxifen.
Everolimus The serum concentration of Everolimus can be increased when it is combined with Tamoxifen.
Rifaximin The serum concentration of Rifaximin can be increased when it is combined with Tamoxifen.
Luliconazole The serum concentration of Tamoxifen can be increased when it is combined with Luliconazole.
Cilostazol The metabolism of Cilostazol can be decreased when combined with Tamoxifen.
Colchicine The serum concentration of Colchicine can be increased when it is combined with Tamoxifen.
Fentanyl The metabolism of Tamoxifen can be decreased when combined with Fentanyl.
Iloperidone The metabolism of Iloperidone can be decreased when combined with Tamoxifen.
Retapamulin The metabolism of Retapamulin can be decreased when combined with Tamoxifen.
Tofacitinib The metabolism of Tofacitinib can be decreased when combined with Tamoxifen.
Vardenafil The metabolism of Vardenafil can be decreased when combined with Tamoxifen.
Zopiclone The metabolism of Zopiclone can be decreased when combined with Tamoxifen.
Lovastatin The metabolism of Lovastatin can be decreased when combined with Tamoxifen.
Metreleptin The metabolism of Tamoxifen can be increased when combined with Metreleptin.
Bexarotene The metabolism of Tamoxifen can be increased when combined with Bexarotene.
Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Tamoxifen.
Alprazolam The metabolism of Alprazolam can be decreased when combined with Tamoxifen.
Atomoxetine The metabolism of Atomoxetine can be decreased when combined with Tamoxifen.
Ospemifene The risk or severity of adverse effects can be increased when Tamoxifen is combined with Ospemifene.
Ifosfamide The metabolism of Ifosfamide can be increased when combined with Tamoxifen.
Perampanel The metabolism of Perampanel can be increased when combined with Tamoxifen.
Anastrozole The serum concentration of Anastrozole can be decreased when it is combined with Tamoxifen.
Letrozole The serum concentration of Letrozole can be decreased when it is combined with Tamoxifen.
Mipomersen Tamoxifen may increase the hepatotoxic activities of Mipomersen.
Lepirudin The risk or severity of bleeding can be increased when Tamoxifen is combined with Lepirudin.
Bivalirudin The risk or severity of bleeding can be increased when Tamoxifen is combined with Bivalirudin.
Alteplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Alteplase.
Urokinase The risk or severity of bleeding can be increased when Tamoxifen is combined with Urokinase.
Reteplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Reteplase.
Anistreplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Anistreplase.
Tenecteplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Tenecteplase.
Abciximab The risk or severity of bleeding can be increased when Tamoxifen is combined with Abciximab.
Drotrecogin alfa The risk or severity of bleeding can be increased when Tamoxifen is combined with Drotrecogin alfa.
Streptokinase The risk or severity of bleeding can be increased when Tamoxifen is combined with Streptokinase.
Dicoumarol The risk or severity of bleeding can be increased when Tamoxifen is combined with Dicoumarol.
Argatroban The risk or severity of bleeding can be increased when Tamoxifen is combined with Argatroban.
Ardeparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Ardeparin.
Phenindione The risk or severity of bleeding can be increased when Tamoxifen is combined with Phenindione.
Fondaparinux The risk or severity of bleeding can be increased when Tamoxifen is combined with Fondaparinux.
Warfarin The risk or severity of bleeding can be increased when Tamoxifen is combined with Warfarin.
Pentosan polysulfate The risk or severity of bleeding can be increased when Tamoxifen is combined with Pentosan polysulfate.
Phenprocoumon The risk or severity of bleeding can be increased when Tamoxifen is combined with Phenprocoumon.
Dipyridamole The risk or severity of bleeding can be increased when Tamoxifen is combined with Dipyridamole.
Heparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Heparin.
Enoxaparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Enoxaparin.
Epoprostenol The risk or severity of bleeding can be increased when Tamoxifen is combined with Epoprostenol.
Acenocoumarol The risk or severity of bleeding can be increased when Tamoxifen is combined with Acenocoumarol.
4-hydroxycoumarin The risk or severity of bleeding can be increased when Tamoxifen is combined with 4-hydroxycoumarin.
Coumarin The risk or severity of bleeding can be increased when Tamoxifen is combined with Coumarin.
Ximelagatran The risk or severity of bleeding can be increased when Tamoxifen is combined with Ximelagatran.
Desmoteplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Desmoteplase.
Defibrotide The risk or severity of bleeding can be increased when Tamoxifen is combined with Defibrotide.
Ancrod The risk or severity of bleeding can be increased when Tamoxifen is combined with Ancrod.
Beraprost The risk or severity of bleeding can be increased when Tamoxifen is combined with Beraprost.
Prasugrel The risk or severity of bleeding can be increased when Tamoxifen is combined with Prasugrel.
Rivaroxaban The risk or severity of bleeding can be increased when Tamoxifen is combined with Rivaroxaban.
Sulodexide The risk or severity of bleeding can be increased when Tamoxifen is combined with Sulodexide.
Semuloparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Semuloparin.
Idraparinux The risk or severity of bleeding can be increased when Tamoxifen is combined with Idraparinux.
Cangrelor The risk or severity of bleeding can be increased when Tamoxifen is combined with Cangrelor.
Astaxanthin The risk or severity of bleeding can be increased when Tamoxifen is combined with Astaxanthin.
Apixaban The risk or severity of bleeding can be increased when Tamoxifen is combined with Apixaban.
Otamixaban The risk or severity of bleeding can be increased when Tamoxifen is combined with Otamixaban.
Amediplase The risk or severity of bleeding can be increased when Tamoxifen is combined with Amediplase.
Danaparoid The risk or severity of bleeding can be increased when Tamoxifen is combined with Danaparoid.
Dalteparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Dalteparin.
Tinzaparin The risk or severity of bleeding can be increased when Tamoxifen is combined with Tinzaparin.

Target Protein

Estrogen receptor ESR1
Estrogen receptor beta ESR2
Protein kinase C PRKCA
Sex hormone-binding globulin SHBG
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase EBP
Androgen receptor AR
Voltage-gated inwardly rectifying potassium channel KCNH2 KCNH2
Nuclear receptor subfamily 1 group I member 2 NR1I2
Estrogen-related receptor gamma ESRRG
Mitogen-activated protein kinase 8 MAPK8

Referensi & Sumber

Synthesis reference: Chengjian Mao, "Tamoxifen and 4-hydroxytamoxifen-activated system for regulated production of proteins in eukaryotic cells." U.S. Patent US20030199022, issued October 23, 2003.
Artikel (PubMed)
  • PMID: 8242225
    Jordan VC: Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol. 1993 Oct;110(2):507-17.
  • PMID: 15639680
    Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2.
  • PMID: 12124303
    Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74.
  • PMID: 25157097
    Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25.
  • PMID: 24328412
    Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168.
  • PMID: 10383884
    White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153.
  • PMID: 15987777
    Parte P, Kupfer D: Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab Dispos. 2005 Oct;33(10):1446-52. doi: 10.1124/dmd.104.000802. Epub 2005 Jun 29.
  • PMID: 27083550
    Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen's oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12.
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