Tamoxifen

Base Information Edit

Chemical Name:Tamoxifen
CAS No.:10540-29-1
Molecular Formula:C26H29NO
Molecular Weight:371.522
Hs Code.:29221990
European Community (EC) Number:234-118-0
NSC Number:727681
UNII:094ZI81Y45
DSSTox Substance ID:DTXSID1034187
Nikkaji Number:J238.685B,J75.058A,J10.452C
Wikipedia:Tamoxifen
NCI Thesaurus Code:C62078
RXCUI:10324
Pharos Ligand ID:77VBQQV883JS
Metabolomics Workbench ID:42990
ChEMBL ID:CHEMBL83
Mol file:10540-29-1.mol

Synonyms:Citrate, Tamoxifen;ICI 46,474;ICI 46474;ICI 47699;ICI-46,474;ICI-46474;ICI-47699;ICI46,474;ICI46474;ICI47699;Nolvadex;Novaldex;Soltamox;Tamoxifen;Tamoxifen Citrate;Tomaxithen;Zitazonium

Suppliers and Price of Tamoxifen

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Tamoxifen
2.5g
$ 418.00

TRC
Tamoxifen
25g
$ 275.00

Tocris
Tamoxifen ≥99%(HPLC)
100
$ 71.00

Sigma-Aldrich
Tamoxifen analytical standard
50mg
$ 56.20

Sigma-Aldrich
Tamoxifen certified reference material, TraceCERT
50mg
$ 98.30

Sigma-Aldrich
Tamoxifensolution 1?mg/mLinmethanol,certifiedreferencematerial,ampuleof1?mL,Cerilliant?
1ML
$ 89.00

Sigma-Aldrich
Tamoxifen ≥99%
1g
$ 242.00

Sigma-Aldrich
Tamoxifen ≥99%
5g
$ 969.00

Medical Isotopes, Inc.
Tamoxifen >99%
1 g
$ 820.00

Medical Isotopes, Inc.
Tamoxifen-d3HCl
1 mg
$ 625.00

Total 161 raw suppliers

Chemical Property of Tamoxifen Edit

Chemical Property:

Appearance/Colour:White crystalline solid
Vapor Pressure:1.85E-09mmHg at 25°C
Melting Point:97-98 °C(lit.)
Refractive Index:1.582
Boiling Point:482.3 °C at 760 mmHg
PKA:pKa 8.71(H2O t = 25 I = 0.025) (Uncertain)
Flash Point:140 °C
PSA：12.47000
Density:1.042 g/cm³
LogP:5.99610
Storage Temp.:2-8°C
Solubility.:H2O: insoluble
Water Solubility.:Insoluble in water. Soluble in methanol, ethanol, propanol or propylene glycol.Soluble in dimethyl sulfoxide, dichloromethane an
XLogP3:7.1
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:371.224914549
Heavy Atom Count:28
Complexity:463

Purity/Quality:

99.5% ^*data from raw suppliers

Tamoxifen ^*data from reagent suppliers

Safty Information:

Pictogram(s): T, Xi
Hazard Codes:T,Xi
Statements: 45-60-61-64-36/37/38
Safety Statements: 53-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Drug Classes:Antineoplastic Agents
Canonical SMILES:CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
Isomeric SMILES:CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
Recent ClinicalTrials:Comparative Evaluation of Efficacy and Safety of Toremifene, Tamoxifen, and Aromatase Inhibitor Plus Ovarian Function Suppression in Hormone Receptor-Positive Early Breast Cancer Among Non-Low-Risk Premenopausal Women: A Real-World Study
Recent EU Clinical Trials:Predicting an accurate tamoxifen dose: a feasibility study in patients with hormone positive breast cancer
Recent NIPH Clinical Trials:A Study Evaluating the Efficacy and Safety of Adjuvant Giredestrant Compared With Physician's Choice of Adjuvant Endocrine Monotherapy in Participants With Estrogen Receptor-Positive, HER2-Negative Early Breast Cancer (lidERA Breast Cancer)
Uses 1. Treatment for Women with metastatic breast cancer recurrence. 2. Used as adjuvant therapy after surgery for breast cancer metastasis, and relapse prevention. 3. For the treatment of ovarian cancer, endometrial cancer and endometriosis. A nonsteroidal estrogen antagonist of interest in the treatment of some forms of breast cancer. Tamoxifen is a Protein Kinase C inhibitor, and induces apoptosis in human malignant glioma cell lines 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. Protein kinase C inhibitor. Induces apoptosis in human malignant glioma cell lines. Tamoxifen and its metabolite 4-hydroxytamoxifen are selective estrogen response mo difiers (SERMs) that act as estrogen antagonists in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells. Tamoxifen has been used to facilitate the recombination of ect2flox allele in mouse organs91. It has also been used to study its effect on lipopolysaccharide (LPS)-induced microglial activation92.
Drug interactions 1. The drug combines with fluorouracil, cyclophosphamide, methotrexate, vincristine and doxorubicin, etc. and can improve the effects. 2. The drug can increase the dopaminergic effect of bromocriptine mesylate. 3. The data show that the drug can prolong neuromuscular blockade of atracurium. 4. The drug can enhance the effect of anticoagulants, not combining with anticoagulants (such as warfarin, two coumarin anticoagulants). 5. Antacids and cimetidine, famotidine, ranitidine can change the pH of the stomach, making the drug enteric-coated tablets decomposed and showing a stimulating effect on the stomach, so when l in combination , these drugs should be interval of 1 to 2 hours. 6. Estrogen can affect the therapeutic effect of the drug, should not be combined. 7. The in vitro test results show that the drug may inhibit the metabolism of tacrolimus. 8.When in combination with mitomycin, the risk of hemolytic syndrome and hematuria increased. 9. The drug combines with triptolide which can lead to accelerate tumor growth in mice, so the combination should be cautious. 10. with allopurinol, the drug may increase liver toxicity. 11. The drug combines with other cytotoxic drugs, increasing the risk of thromboembolism. Potentially hazardous interactions with other drugs Anticoagulants: effects of coumarins enhanced. Antidepressants: metabolism of tamoxifen to active metabolite possibly inhibited by fluoxetine and paroxetine - avoid. Antipsychotics: increased risk of ventricular arrhythmias with droperidol - avoid. Buproprion: metabolism of tamoxifen to active metabolite possibly inhibited - avoid. Cinacalcet: metabolism of tamoxifen to active metabolite possibly inhibited - avoid.
Description In 1966, ICI Pharmaceuticals (now AstraZeneca) first synthesized tamoxifen in the hope of developing a morning-after contraceptive pill. The UK patent for this compound was in place in 1962, whereas the US patent was repeatedly denied until the 1980s. Tamoxifen was approved for a fertility treatment but it was not proven as useful in regulating human contraception. Even though there was a link between estrogen and breast cancer, developing a cancer treatment was not a priority at the time. In 1971, the first clinical study showed a convincing effect of tamoxifen in treating advanced breast cancer. From 1971 to 1977, this drug was neither clinically nor financially remarkable. In 1980s, however, publications first showed that tamoxifen, in addition to chemotherapy, improved survival for patients with early stage breast cancer. In 1998, the meta-analysis by the Oxford-based Early Breast Cancer Trialists’ Collaborative Group showed that tamoxifen did indeed save lives in early breast cancer. In 2001, tamoxifen sales were over $1.024 billion. Since the expiration of the patent in 2002, it is now widely available as a generic drug. By 2004, tamoxifen was the best selling hormonal drug for the treatment of breast cancer.
Indications Tamoxifen (Nolvadex) is a synthetic antiestrogen used in the treatment of breast cancer. Normally, estrogens act by binding to a cytoplasmic protein receptor, and the resulting hormone–receptor complex is then translocated into the nucleus, where it induces the synthesis of ribosomal RNA (rRNA) and messenger RNA (mRNA) at specific sites on the DNA of the target cell. Tamoxifen also avidly binds to estrogen receptors and competes with endogenous estrogens for these critical sites. The drug–receptor complex has little or no estrogen agonist activity.Tamoxifen directly inhibits growth of human breast cancer cells that contain estrogen receptors but has little effect on cells without such receptors. Tamoxifen is a partial estrogen agonist in breast and thus is used as a treatment and chemopreventative for breast cancer. Tamoxifen is a full agonist in bone and endometrium, and prolonged use of tamoxifen leads to a fourfold to fivefold increase in the incidence of endometrial cancer. See Chapter 56 for a detailed discussion of the use of tamoxifen in breast cancer.
Therapeutic Function Antiestrogen, Antineoplastic
Clinical Use Tamoxifen is a SERM that is used as an antiestrogen in the treatment of estrogen-dependent breas Tcancer following prim ary treatment (c hemotherapy and/or surgery).

Technology Process of Tamoxifen

There total 186 articles about Tamoxifen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%