Flutamide | CAS#13311-84-7 | antiandrogen

MedKoo Cat#: 100374 | Name: Flutamide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Flutamide, also known as SCH13521, is a toluidine derivative and nonsteroidal antiandrogen that is structurally related to bicalutamide and nilutamide. Flutamide and its more potent active metabolite 2-hydroxyflutamide competitively block dihydrotestosterone binding at androgen receptors, forming inactive complexes which cannot translocate into the cell nucleus. Formation of inactive receptors inhibits androgen-dependent DNA and protein synthesis, resulting in tumor cell growth arrest or transient tumor regression. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Flutamide

CAS#13311-84-7

Theoretical Analysis

MedKoo Cat#: 100374

Name: Flutamide

CAS#: 13311-84-7

Chemical Formula: C11H11F3N2O3

Exact Mass: 276.0722

Molecular Weight: 276.21

Elemental Analysis: C, 47.83; H, 4.01; F, 20.63; N, 10.14; O, 17.38

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 190.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 400.00	2 weeks
10g	USD 650.00	2 weeks

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Related CAS #

223134-72-3 (d7) 13311-84-7

Synonym

SCH13521; SCH-13521; SCH 13521; Flucinom; Flugerel; Niftolid; Eulexin; Apimid; Chimax; Drogenil; Euflex; Eulexine; Flucinome; Fluken; Flulem; Flutabene; Flutacan; FlutaGry; Flutamex; Flutamin; Flutan; Flutaplex; Fugerel; Grisetin; Oncosal; Profamid; Prostacur; Prostadirex; Prostica; Prostogenat; Tafenil; Tecnoflut; Testotard. FLUT.

IUPAC/Chemical Name

N-(4-nitro-3-(trifluoromethyl)phenyl)isobutyramide

InChi Key

MKXKFYHWDHIYRV-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)

SMILES Code

CC(C)C(NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

DRUG DESCRIPTION EULEXIN Capsules contain flutamide, an acetanilid, nonsteroidal, orally active anti-androgen having the chemical name, 2-methyl-N-[4-nitro-3 (trifluoromethyl) phenyl] propanamide. Each capsule contains 125 mg flutamide. The compound is a buff to yellow powder with a molecular weight of 276.2. The inactive ingredients for EULEXIN Capsules include: corn starch, lactose, magnesium stearate, povidone, and sodium lauryl sulfate. Gelatin capsule shells may contain methylparaben, propylparaben, butylparaben, and the following dye systems: FD&C Blue 1, FD&C Yellow 6, and either FD&C Red 3 or FD&C Red 40 plus D&C Yellow 10, with titanium dioxide and other inactive ingredients. Use in prostate cancer Gonadotropin-releasing hormone (GnRH) is released by the hypothalamus in a pulsatile fashion; this causes the anterior pituitary gland to release luteinizing hormone (LH) and follicle-stimulating hormone (FSH). LH stimulates the testes to produce testosterone, which is metabolized to DHT by the enzyme 5α-reductase. DHT, and to a much smaller extent, testosterone, stimulate prostate cancer cells to grow. Therefore, blocking these androgens can provide powerful treatment for prostate cancer, especially metastatic disease. Normally administered are analogues of GnRH, such as leuprolide or goserelin. Although they stimulate the same receptors that GnRH does, since they are present continuously and not in a pulsatile manner, they serve to inhibit the pituitary and therefore block the whole chain. However, they initially cause a surge in activity; this is not solely a theoretical risk but may cause the cancer to flare. Flutamide was initially used at the beginning of GnRH-analogue therapy to block this surge, and it and other nonsteroidal anti-androgens continue in this use. There have been studies to investigate the benefit of adding an anti-androgen to surgical orchiectomy or its continued use with a GnRH analogue (combined androgen blockade, CAB). Adding anti-androgens to orchiectomy showed no benefit, while a small benefit was shown with adding anti-androgens to GnRH analogues Unfortunately, therapies which lower testosterone levels, such as orchiectomy or GnRH-analogue administration, also have significant side effects. Compared to these therapies, treatment with antiandrogens exhibits "fewer hot flashes, less of an effect on libido, less muscle wasting, fewer personality changes, and less bone loss." However, antiandrogen therapy alone is less effective than surgery. Nevertheless, given the advanced age of many with prostate cancer, as well as other features, many men may choose antiandrogen therapy alone for a better quality of life. From: http://en.wikipedia.org/wiki/Flutamide.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TCI50814

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Flutamide (SCH-13521) is an antiandrogen drug, with its active metablolite binding at androgen receptor with Ki values of 55 nM, and primarily used to treat prostate cancer.

In vitro activity:

This study was designed to delineate the role of Nrf2/HO-1 in flutamide-induced hepatic cell injury. The results showed that flutamide concentration dependently induced cytotoxicity, hydrogen peroxide accumulation, and mitochondrial dysfunction as indicated by mitochondrial membrane potential loss and ATP depletion. The protein expression of Nrf2 and HO-1 was induced by flutamide at 12.5 μM but was downregulated by higher concentrations of flutamide. Silencing either Nrf2 or HO-1 was found to aggravate flutamide-induced hydrogen peroxide accumulation and mitochondrial dysfunction as well as inhibition of the Nrf2 pathway. Moreover, preinduction of HO-1 by Copp significantly attenuated flutamide-induced oxidative stress and mitochondrial dysfunction, while inhibition of HO-1 by Snpp aggravated these deleterious effects. These findings suggest that flutamide-induced hepatic cell death and mitochondrial dysfunction is assoicated with inhibition of Nrf2-mediated HO-1. Reference: Oxid Med Cell Longev. 2018 Jul 2;2018:8017073. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30057686/

In vivo activity:

All the male pups which randomly selected for anatomy and measurement of reproductive organs had no changes of the urethra, genital phenotype, and histology in the control group, while those in the flutamide group were with hypospadias, and the incidence rate was 100% (Figure 1(a)). The body mass of the control group (39.67 ± 3.23 g) was more than that of the flutamide (37.21 ± 2.89 g; p < 0.05). Their AGD and penis length were shorter than those of the control (Figure 1(a) and (b)). The blood vessels on the testicular surface of the control group were more abundant than the flutamide group, and the testicular volume of the flutamide group was smaller than that of the control, showing a “small testicle” (Figure 1(c)). Reference: Hum Exp Toxicol. 2020 Dec;39(12):1690-1699. https://journals.sagepub.com/doi/10.1177/0960327120937049?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed

	Solvent	mg/mL	mM
Solubility
	DMSO	55.0	199.12
	Ethanol	55.0	199.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 276.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Zhang L, Guo J, Zhang Q, Zhou W, Li J, Yin J, Cui L, Zhang T, Zhao J, Carmichael PL, Middleton A, Peng S. Flutamide Induces Hepatic Cell Death and Mitochondrial Dysfunction via Inhibition of Nrf2-Mediated Heme Oxygenase-1. Oxid Med Cell Longev. 2018 Jul 2;2018:8017073. doi: 10.1155/2018/8017073. PMID: 30057686; PMCID: PMC6051009. 2. Hejmej A, Bilinska B. The effects of flutamide on cell-cell junctions in the testis, epididymis, and prostate. Reprod Toxicol. 2018 Oct;81:1-16. doi: 10.1016/j.reprotox.2018.06.014. Epub 2018 Jun 26. PMID: 29958919.

In vivo protocol:

1. Yu H, Wen K, Zhou X, Zhang Y, Yan Z, Fu H, Zhu J, Zhu Y. Role of unfolded protein response in genital malformation/damage of male mice induced by flutamide. Hum Exp Toxicol. 2020 Dec;39(12):1690-1699. doi: 10.1177/0960327120937049. Epub 2020 Jul 14. PMID: 32662666. 2. Hejmej A, Bilinska B. The effects of flutamide on cell-cell junctions in the testis, epididymis, and prostate. Reprod Toxicol. 2018 Oct;81:1-16. doi: 10.1016/j.reprotox.2018.06.014. Epub 2018 Jun 26. PMID: 29958919.

1: Medina-Rojas JC, Castillo-Rodríguez IO, Martínez-Klimova E, Ramírez-Ápan T, Hernández-Ortega S, Martínez-García M. Synthesis of flutamide-conjugates. Bioorg Med Chem Lett. 2020 Nov 1;30(21):127507. doi: 10.1016/j.bmcl.2020.127507. Epub 2020 Aug 28. PMID: 32866675. 2: Giorgetti R, di Muzio M, Giorgetti A, Girolami D, Borgia L, Tagliabracci A. Flutamide-induced hepatotoxicity: ethical and scientific issues. Eur Rev Med Pharmacol Sci. 2017 Mar;21(1 Suppl):69-77. PMID: 28379593. 3: Wysowski DK, Fourcroy JL. Flutamide hepatotoxicity. J Urol. 1996 Jan;155(1):209-12. Erratum in: J Urol 1996 Apr;155(4):1396. PMID: 7490837. 4: Goldspiel BR, Kohler DR. Flutamide: an antiandrogen for advanced prostate cancer. DICP. 1990 Jun;24(6):616-23. doi: 10.1177/106002809002400612. PMID: 2193461. 5: Dumesic DA, Winnett C, Lu G, Grogan TR, Abbott DH, Naik R, Chazenbalk GD. Randomized clinical trial: effect of low-dose flutamide on abdominal adipogenic function in normal-weight women with polycystic ovary syndrome. Fertil Steril. 2023 Jan;119(1):116-126. doi: 10.1016/j.fertnstert.2022.09.324. Epub 2022 Nov 15. PMID: 36400597. 6: Schott AM, Vial T, Gozzo I, Chareyre S, Delmas PD. Flutamide-induced methemoglobinemia. DICP. 1991 Jun;25(6):600-1. doi: 10.1177/106002809102500606. PMID: 1877268. 7: Madan RA, Bilusic M, Stein MN, Donahue RN, Arlen PM, Karzai F, Plimack E, Wong YN, Geynisman DM, Zibelman M, Mayer T, Strauss J, Chen G, Rauckhorst M, McMahon S, Couvillon A, Steinberg S, Figg WD, Dahut WL, Schlom J, Gulley JL. Flutamide With or Without PROSTVAC in Non-metastatic Castration Resistant (M0) Prostate Cancer. Oncologist. 2023 Jul 5;28(7):642-e561. doi: 10.1093/oncolo/oyad058. PMID: 37134294; PMCID: PMC10322134. 8: Borroni G, Brazzelli V, Baldini F, Borghini F, Gaviglio MR, Beltrami B, Nolli G. Flutamide-induced pseudoporphyria. Br J Dermatol. 1998 Apr;138(4):711-2. doi: 10.1046/j.1365-2133.1998.02197.x. PMID: 9640390. 9: Sogani PC, Whitmore WF Jr. Flutamide and other antiandrogens in the treatment of advanced prostatic carcinoma. Cancer Treat Res. 1988;39:131-45. doi: 10.1007/978-1-4613-1731-9_9. PMID: 2908604. 10: Khan AM, Singh NT, Bilgrami S. Flutamide induced methemoglobinemia. J Urol. 1997 Apr;157(4):1363. PMID: 9120948. 11: Møller S, Iversen P, Franzmann MB. Flutamide-induced liver failure. J Hepatol. 1990 May;10(3):346-9. doi: 10.1016/0168-8278(90)90144-g. PMID: 2365984. 12: Leroy D, Dompmartin A, Szczurko C. Flutamide photosensitivity. Photodermatol Photoimmunol Photomed. 1996 Oct;12(5):216-8. doi: 10.1111/j.1600-0781.1996.tb00203.x. PMID: 9112281. 13: Brogden RN, Clissold SP. Flutamide. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in advanced prostatic cancer. Drugs. 1989 Aug;38(2):185-203. doi: 10.2165/00003495-198938020-00003. PMID: 2670515. 14: Tsien C, Souhami L. Flutamide photosensitivity. J Urol. 1999 Aug;162(2):494. PMID: 10411069. 15: Neri R. Pharmacology and pharmacokinetics of flutamide. Urology. 1989 Oct;34(4 Suppl):19-21; discussion 46-56. doi: 10.1016/0090-4295(89)90230-6. PMID: 2477934. 16: Brogden RN, Chrisp P. Flutamide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in advanced prostatic cancer. Drugs Aging. 1991 Mar;1(2):104-15. doi: 10.2165/00002512-199101020-00003. PMID: 1794008. 17: Cohen MR. Flutamide or thalidomide? Nursing. 2004 Jun;34(6):18. doi: 10.1097/00152193-200406000-00012. PMID: 15187694. 18: Motta T, Maggi G, D'Alberton A. Flutamide and hirsutism. J Endocrinol Invest. 1994 Sep;17(8):673. doi: 10.1007/BF03349685. PMID: 7868809. 19: Grimaldi F, Proto G, Bertolissi F. Flutamide--effects and side effects. Fertil Steril. 1993 Apr;59(4):937. doi: 10.1016/s0015-0282(16)55890-7. PMID: 8458522. 20: Hart W, Stricker BH. Flutamide and hepatitis. Ann Intern Med. 1989 Jun 1;110(11):943-4. doi: 10.7326/0003-4819-110-11-943_2. PMID: 2719431.

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ABT-279

MedKoo CAT#: 524117

CAS#: 676559-83-4