(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine

• ChemBase ID: 557
• Molecular Formular: C26H29NO
• Molecular Mass: 371.51456
• Monoisotopic Mass: 371.22491455
• SMILES: O(c1ccc(/C(=C(/CC)\c2ccccc2)/c2ccccc2)cc1)CCN(C)C
• Canonical SMILES: CC/C(=C(\c1ccccc1)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
• 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-
• InChIKey: NKANXQFJJICGDU-QPLCGJKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine; {2-[4-(1,2-diphenylbut-1-en-1-yl)phenoxy]ethyl}dimethylamine
• IUPAC Traditional name: tamoxifen; {2-[4-(1,2-diphenylbut-1-en-1-yl)phenoxy]ethyl}dimethylamine
• Brand Name: Apo-Tamox; Citofen; Crisafeno; Diemon; Gen-Tamoxifen; Istubol; Kessar; Noltam; Nolvadex; Nolvadex-D; Nourytam; Novo-Tamoxifen; Oncomox; PMS-Tamoxifen; Retaxim; Tamizam; Tamofen; Tamone; Tamoxasta; Tamoxen; Valodex; Zemide
• Synonyms: Tamoxifenum [INN-Latin]; Tamoxifeno [INN-Spanish]; Tamoxifene [INN-French]; Trans-Tamoxifen; Tamoxifen Citrate; Tamoxifen; Tamoxifen; (E/Z)-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine; 1-[p-[2-(N,N-Dimethylamino)ethoxy] phenyl]-1,2-diphenylbut-1-ene; (E/Z)-Mammaton; (E/Z)-Novaldex; (E/Z)-Tamoxifen; (Z)-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine; ICI 47699; Mammaton; Novaldex; Tamoxifen; Z-Tamoxifen; (Z)-1-(对二甲基氨基乙氧基苯基)-1,2-二苯基-1-丁烯; (Z)-2-[4-(1,2-二苯基-1-丁烯)苯氧基]-N,N-二甲基乙胺; 他莫昔芬

Database IDs

• CAS Number: 7728-73-6; 10540-29-1
• EC Number: 234-118-0
• MDL Number: MFCD00010454
• PubChem SID: 46505515; 24900307; 160964020
• PubChem CID: 2733526

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2851102
• LogD (pH = 7.4): 4.971639
• Log P: 6.351222
• Molar Refractivity: 128.4308 cm^3
• Polarizability: 46.4946 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.93
• LOG S: -5.56
• Solubility (Water): 1.02e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.000167 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; Dichloromethane
• Apperance: White Crystalline Solid
• Melting Point: 92-94°C; 97-98 °C(lit.)
• Hydrophobicity(logP): 7.1

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer
• RTECS: KR5919600
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-60-61-64
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350-H360-H362
• GHS Precautionary statements: P201-P263-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544), EBP(10682), ESR1(2099), ESR2(2100), ESRRA(2101)rat ... Ar(24208), Esr1(24890)

Product Information

• Purity: ≥99%; 98%

DETAILS

DrugBank - DB00675

• Drug Groups: approved
• Description: One of the selective estrogen receptor modulators with tissue-specific activities. 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]
• Indication: For the treatment of breast cancer.
• Pharmacology: 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.
• Toxicity: Signs observed at the highest doses following studies to determine LD₅₀ in animals were respiratory difficulties and convulsions.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Tamoxifen is extensively metabolized after oral administration. N-Desmethyl-tamoxifen is the major metabolite found in plasma. N-Desmethyl-tamoxifen 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.
• Half Life: Distribution t_1/2=7 to 14 hours; Elimination t_1/2=5 to 7 days; Elimination t_1/2 of N-desmethyl-tamoxifen=9-14 days.
• Elimination: The drug is excreted mainly as polar conjugates, with unchanged drug and unconjugated metabolites accounting for less than 30% of the total fecal radioactivity.
• References: Jordan VC: Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol. 2006 Jan;147 Suppl 1:S269-76. [Pubmed] ; 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. [Pubmed] ; 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. [Pubmed] ; Steiner AZ, Terplan M, Paulson RJ: Comparison of tamoxifen and clomiphene citrate for ovulation induction: a meta-analysis. Hum Reprod. 2005 Jun;20(6):1511-5. Epub 2005 Apr 21. [Pubmed] ; van Bommel EF, Hendriksz TR, Huiskes AW, Zeegers AG: Brief communication: tamoxifen therapy for nonmalignant retroperitoneal fibrosis. Ann Intern Med. 2006 Jan 17;144(2):101-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T5648

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
General description
Tamoxifen is a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor. Tamoxifen is a prodrug that is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. In breast cancer, the gene repressor activity of tamoxifen against ERBB2 is dependent upon PAX2. Blocks estradiol-stimulated VEGF production in breast tumor cells.
Biochem/physiol Actions
蛋白激酶 C 抑制剂。诱发人类恶性神经胶质瘤细胞系的细胞凋亡。他莫昔芬及其代谢产物 4-羟基他莫昔芬是选择性雌激素反应调节剂 (SERM)，在乳腺中用作雌激素拮抗剂。阻止乳腺肿瘤细胞中雌二醇刺激的 VEGF 的产生。

Toronto Research Chemicals - T006000

Tamoxifen is a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor. Tamoxifen is a prodrug that is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2

Toronto Research Chemicals - T006005

Mixture of Tamoxifen and its (E)-isomer.

REFERENCES

• Jordan VC: Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol. 2006 Jan;147 Suppl 1:S269-76. Pubmed
• 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. Pubmed
• 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. Pubmed
• Steiner AZ, Terplan M, Paulson RJ: Comparison of tamoxifen and clomiphene citrate for ovulation induction: a meta-analysis. Hum Reprod. 2005 Jun;20(6):1511-5. Epub 2005 Apr 21. Pubmed
• van Bommel EF, Hendriksz TR, Huiskes AW, Zeegers AG: Brief communication: tamoxifen therapy for nonmalignant retroperitoneal fibrosis. Ann Intern Med. 2006 Jan 17;144(2):101-6. Pubmed
• Lerner, L., et al.: Cancer Res., 50, 4177 (1977)
• Love, R., et al.: J. Clin. Oncol., 20 2559 (1977)
• Sutherland, R., et al.: Nature, 267, 434 (1977)
• Collins, D., et al.: J. Med. Chem., 14, 952 (1971)