The solution stability of this product in corn oil has not been determined. However, other sources state that solutions of tamoxifen in corn oil can be stored at 4°C for up to a week.
T5648
Tamoxifen
Tamoxifen
1 of 2 reviewers received a sample product or took part in a promotion
≥99% (TLC), powder, PKC inhibitor
Synonym(s):
trans-Tamoxifen, (Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine
Sign Into View Organizational & Contract Pricing
Select a Size
1 G
PLN 2,500.00
5 G
PLN 5,290.00
All Photos(4)
Select a Size
Change View
1 G
PLN 2,500.00
5 G
PLN 5,290.00
About This Item
Linear Formula:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS Number:
Molecular Weight:
371.51
EC Number:
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.54
Recommended Products
Product Name
Tamoxifen, ≥99%
sterility
(Not packaged in a sterile environment)
Assay
≥99%
mp
97-98 °C (lit.)
solubility
H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble
antibiotic activity spectrum
neoplastics
Mode of action
enzyme | inhibits
originator
AstraZeneca
storage temp.
2-8°C
SMILES string
CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3
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
NKANXQFJJICGDU-QPLCGJKRSA-N
Gene Information
human ... CYP1A2(1544) , EBP(10682) , ESR1(2099) , ESR2(2100) , ESRRA(2101)
rat ... Ar(24208) , Esr1(24890)
Looking for similar products? Visit Product Comparison Guide
General description
Tamoxifen (TC), a selective estrogen receptor modulator (SERM), is used against breast cancer in both men and women. It also acts as a prophylactic agent against breast cancer in women.[1] This protein kinase C inhibitor and anti-angiogenetic factor 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. TC blocks estradiol-stimulated vascular endothelial growth factor (VEGF) production in breast tumor cells. Patients with estrogen receptor-positive tumors are more likely to benefit from tamoxifen. It exhibits both estrogenic agonist and antagonist effects by selectively binding to estrogen receptors in different parts of the body.[1]
This nonsteroidal triphenylethylene derivative suppresses tumor growth and has been reported to be a carcinogen and teratogen in animals. Additionally, TC may also protect bone from estrogen-deficiency bone loss, lower plasma cholesterol, and have been implicated in liver carcinogenesis in rats. Other actions of TC include the reduction of plasma levels of insulin-like growth factor, induction of cells surrounding cancer cells to secrete transforming growth factor β, and inhibition of membrane lipid peroxidation, likely by decreasing membrane fluidity.
This nonsteroidal triphenylethylene derivative suppresses tumor growth and has been reported to be a carcinogen and teratogen in animals. Additionally, TC may also protect bone from estrogen-deficiency bone loss, lower plasma cholesterol, and have been implicated in liver carcinogenesis in rats. Other actions of TC include the reduction of plasma levels of insulin-like growth factor, induction of cells surrounding cancer cells to secrete transforming growth factor β, and inhibition of membrane lipid peroxidation, likely by decreasing membrane fluidity.
Application
Tamoxifen has been used:
- in the MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) assay and crystal violet staining assay to access cell viability[2] [3]
- to induce Dicer ablation in Dicer-conditional mice, to study the effects of Dicer deficiency on adipocyte differentiation and function.[4]
- to study its biological effects on the glucocorticoid (GC)-resistant cell line Jurkat, derived from acute lymphoblastic leukemia of T lineage (T-ALL)[5]
- to study the physiological effects of tamoxifen treatment on the hypothalamus-POA mediated by estrogen receptor alpha (ERα) in mice[6]
- to induce Cre recombinase activity for gene manipulation.[7]
- to facilitate the recombination of the ect2flox allele in mouse organs
- to study its effect on lipopolysaccharide (LPS)-induced microglial activation
Biochem/physiol Actions
Protein kinase C inhibitor. Induces apoptosis in human malignant glioma cell lines. Tamoxifen and its metabolite 4-hydroxytamoxifen are selective estrogen response modifiers (SERMs) that act as estrogen antagonists in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells.
Features and Benefits
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Preparation Note
Tamoxifen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution. It is also soluble in methanol, ethanol, 2-propanol and propylene glycol. Stock solutions of tamoxifen can also be prepared in DMSO at 10 mM. However, it is practically insoluble in water (solubility is <0.01%, 20° C). Solutions are sensitive to UV light, and DMSO solutions are stable when stored at -20° C in the dark.
Storage and Stability
Tamoxifen is relatively stable. The powder should be stable for at least two years when stored desiccated at 2-8C, protected from light.
Other Notes
This product is not packaged in a sterile environment.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Choose from one of the most recent versions:
Certificates of Analysis (COA)
Lot/Batch Number
Don't see the Right Version?
If you require a particular version, you can look up a specific certificate by the Lot or Batch number.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
Microglia-Specific Expression of Olfml3 Is Directly Regulated by Transforming Growth Factor ?1-Induced Smad2 Signaling
Neidert N, et al.
Frontiers in Immunology, 9, 1728-1728 (2018)
Bon-Kyoung Koo et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(24), 7548-7550 (2015-05-30)
Rnf43 (RING finger protein 43) and Znrf3 (zinc/RING finger protein 3) (RZ) are two closely related transmembrane E3 ligases, encoded by Wnt target genes, that remove surface Wnt (wingless-int) receptors. The two genes are mutated in various human cancers. Such
Meimei Liu et al.
Aquatic toxicology (Amsterdam, Netherlands), 213, 105220-105220 (2019-06-16)
Tamoxifen (TAM) is an antiestrogenic agent and can enter the aquatic environment in wastewater. It has been reported that TAM can induce hepatic steatosis in vertebrates, however, the effects of TAM exposure on lipid metabolism of hepatopancreas in crustaceans remains
Anna Barkovskaya et al.
Scientific reports, 10(1), 16992-16992 (2020-10-14)
In this study, we probed the importance of O-GlcNAc transferase (OGT) activity for the survival of tamoxifen-sensitive (TamS) and tamoxifen-resistant (TamR) breast cancer cells. Tamoxifen is an antagonist of estrogen receptor (ERα), a transcription factor expressed in over 50% of
Tamoxifen
Farrar MC and Jacobs TF
StatPearls [Internet] (2023)
Articles
We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance
Discover Bioactive Small Molecules for ADME/Tox
Related Content
Explore protein pathway analysis through chemical library screening, investigating protein interactions, and modulating signaling pathways with small molecules.
Chromatograms
application for HPLC, application for SPE-
Tamoxifen was dissolved in corn oil (20mg/ml concentration). Can this solution be stored long term and how? Thank you.
1 answer-
Helpful?
-
-
Is this product pharmaceutical grade?
1 answer-
This product is intended for research use only. At this time, a pharmaceutical-grade product option is not available.
Helpful?
-
-
Hello, Thank you for your product. According to my protocol, I have to dissolve Tamoxifen in the corn oil at the final concentration of 40 mg/ml and feed my mice with that. However, it's insoluble. How can I resolve it? Thank you, Hossein
1 answer-
This product is soluble in chloroform (50 mg/mL, clear, colorless to faintly yellow), 2-propanol, DMSO (10 mM), ethanol, methanol and propylene glycol. Kindly review the information on the product datasheet available at this link: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/389/852/t5648pis.pdf
Corn oil has also been used as a vehicle for tamoxifen as cited by Whitfield J, Littlewood T, Soucek L. Tamoxifen administration to mice. Cold Spring Harb Protoc. 2015 Mar 2;2015(3):269-71. doi: 10.1101/pdb.prot077966. PMID: 25734062; PMCID: PMC6773604. Kindly also review the details at this link: https://www.jax.org/research-and-faculty/resources/cre-repository/tamoxifen
Helpful?
-
-
If I want to use 20mg of tamoxifen, could I only dissolve part of tamoxifen and then store the rest of the powder at refrigerator? Or do I have to dissolve all vial at once?
1 answer-
Tamoxifen is relatively stable. Any required amount can be weighed up for use as needed and the bottle resealed. The powder should be stable for at least two years when stored desiccated at 2-8C, and protected from light.
Helpful?
-
-
Is this product sterile?
1 answer-
This product is not packaged in a sterile environment.
Helpful?
-
-
What is the solubility of tamoxifen, Product No. T5648?
1 answer-
Tamoxifen is tested for solubility in chloroform at a concentration of 50mg/mL. This yields a colorless to faint yellow solution. Tamoxifen is practically insoluble in water. It has been reported to be soluble in methanol, ethanol, 2-propanol and propylene glycol. This product is also reported to be soluble in DMSO at 10mM concentration. Reference for DMSO solubility: Wong, K.R., et al., Am. J. Physiol. Heart Circ. Physiol., 277, H1403-H1409 (1999). Please also see the product information sheet (under Documents, above) for more information on the solubility of this product.
Helpful?
-
-
What is the stability of tamoxifen (e.g., Product No. T5648) once in solution?
1 answer-
Solutions of tamoxifen are sensitive to UV light. According to C.A. O'Brian et al., [Cancer Res. 45, 2462 (1985)], tamoxifen when dissolved in DMSO can be stored at -20°C in the dark. We generally recommend making the solution fresh right before each use.
Helpful?
-
-
What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
Helpful?
-
-
How do I find the expiration date of the bottle of Product No T5648, Tamoxifen, in my possession?
1 answer-
According to Sigma Quality Control Data, T5648 (tamoxifen) should be stable for at least two years if stored dessicated at 2-8°C in the dark. However, there is not an established expiration or retest date for Tamoxifen. This product is guaranteed for 1 year from shipment, if stored correctly and unopened.
Helpful?
-
Active Filters
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service
