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7728-73-6 molecular structure
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(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 and InChIs

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

Cite this record

CBID:557 http://www.chembase.cn/molecule-557.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
7728-73-6
10540-29-1
EC Number
234-118-0
MDL Number
MFCD00010454
PubChem SID
24900307
46505515
160964020
PubChem CID
2733526

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 3.2851102  LogD (pH = 7.4) 4.971639 
Log P 6.351222  Molar Refractivity 128.4308 cm3
Polarizability 46.4946 Å3 Polar Surface Area 12.47 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.93  LOG S -5.56 
Solubility (Water) 1.02e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.000167 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] expand Show data source
Dichloromethane expand Show data source
Apperance
White Crystalline Solid expand Show data source
Melting Point
92-94°C expand Show data source
97-98 °C(lit.) expand Show data source
Hydrophobicity(logP)
7.1 expand Show data source
Storage Condition
Amber Vial, -20°C Freezer expand Show data source
RTECS
KR5919600 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-60-61-64 expand Show data source
Safety Statements
53-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H350-H360-H362 expand Show data source
GHS Precautionary statements
P201-P263-P308 + P313 expand Show data source
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 expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... CYP1A2(1544), EBP(10682), ESR1(2099), ESR2(2100), ESRRA(2101)rat ... Ar(24208), Esr1(24890) expand Show data source
Purity
≥99% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00675 external link
Item Information
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 t1/2=7 to 14 hours; Elimination t1/2=5 to 7 days; Elimination t1/2 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 external link
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 external link
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 external link
Mixture of Tamoxifen and its (E)-isomer.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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