Nilutamide | CAS#63612-50 | MedKoo Biosciences

MedKoo Cat#: 100667 | Name: Nilutamide

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Description:

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

Nilutamide is an antiandrogen medication used in the treatment of advanced-stage prostate cancer. Nilutamide blocks the androgen receptor, preventing its interaction with testosterone. Because most prostate cancer cells rely on the stimulation of the androgen receptor for growth and survival, nilutamide can prolong life in men with prostate cancer. Nilutamide is marketed under the name Nilandron in the United States and under the name Anandron in Canada. (Source: http://en.wikipedia.org/wiki/Nilutamide)

Chemical Structure

Nilutamide

CAS#63612-50-0

Theoretical Analysis

MedKoo Cat#: 100667

Name: Nilutamide

CAS#: 63612-50-0

Chemical Formula: C12H10F3N3O4

Exact Mass: 317.0623

Molecular Weight: 317.22

Elemental Analysis: C, 45.43; H, 3.18; F, 17.97; N, 13.25; O, 20.17

Price and Availability

Size	Price	Availability
200mg	USD 350.00	2 Weeks
1g	USD 750.00	2 Weeks
2g	USD 1,250.00	2 Weeks

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Synonym

NILANDRON 55dimethyl34nitro3(trifluoromethyl)phenyl24imidazolidinedione

IUPAC/Chemical Name

5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dione

InChi Key

XWXYUMMDTVBTOU-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)

SMILES Code

O=C1N(C2=CC=C([N+]([O-])=O)C(C(F)(F)F)=C2)C(C(C)(C)N1)=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

Nilutamide is an antiandrogen medication used in the treatment of advanced stage prostate cancer. Nilutamide blocks the androgen receptor, preventing its interaction with testosterone. Because most prostate cancer cells rely on the stimulation of the androgen receptor for growth and survival, nilutamide can prolong life in men with prostate cancer. Nilutamide is marketed under the name Nilandron in the United States and under the name Anandron in Canada. NILANDRONÂ® tablets contain nilutamide, a nonsteroidal, orally active antiandrogen having the chemical name 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione. Nilutamide is a microcrystalline, white to practically white powder with a molecular weight of 317.25. Its molecular formula is C12H10F3N3O4. It is freely soluble in ethyl acetate, acetone, chloroform, ethyl alcohol, dichloromethane, and methanol. It is slightly soluble in water [ < 0.1% W/V at 25Â°C (77Â°F)]. It melts between 153Â°C and 156Â°C (307.4Â°F and 312.8Â°F). Each NILANDRON tablet contains 150 mg of nilutamide. Other ingredients in NILANDRON tablets are corn starch, lactose, povidone, docusate sodium, magnesium stearate, and talc. Mechanism of Action: Prostate cancer is known to be androgen sensitive and responds to androgen ablation. In animal studies, nilutamide has demonstrated antiandrogenic activity without other hormonal (estrogen, progesterone, mineralocorticoid, and glucocorticoid) effects. In vitro, nilutamide blocks the effects of testosterone at the androgen receptor level. In vivo, nilutamide interacts with the androgen receptor and prevents the normal androgenic response.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nilutamide (Nilandron) is an orally active nonsteroidal androgen receptor antagonist.

In vitro activity:

Although both T and DHT had marginal effects on AR mRNA expression level and cell growth in vitro, the nonsteroidal antiandrogen nilutamide significantly stimulated ESC growth and induced Akt expression. The enhancing effects of nilutamide on mouse ESCs indicated that the Akt pathway may be involved in nilutamide-promoted ESC growth. Reference: Fertil Steril. 2006 Apr;85 Suppl 1:1195-203. https://pubmed.ncbi.nlm.nih.gov/16616092/

In vivo activity:

A last series of experiments was performed after administration of nilutamide in mice. Thirty minutes after administration of doses (15 or 30 mumol.kg-1 i.p.) similar to those used in humans, the hexobarbital sleeping time was increased by 40 and 60%, respectively. There was no evidence, however, for the irreversible inactivation of microsomal enzymes since CO-binding cytochrome P-450 and monooxygenase activities remained unchanged in liver microsomes from mice killed 1 or 6 hr after administration of nilutamide (30 mumol.kg-1 i.p.). These results show that nilutamide inhibits hepatic cytochrome P-450 activity, and suggest that inhibition may actually occur after therapeutic doses of nilutamide in humans. Reference: Biochem Pharmacol. 1989 Mar 15;38(6):941-7. https://pubmed.ncbi.nlm.nih.gov/2930595/

	Solvent	mg/mL	mM
Solubility
	DMSO	156.5	493.35
	Ethanol	63.0	198.60

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 317.22 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:

1. Brancaleone V, Vellecco V, Matassa DS, d'Emmanuele di Villa Bianca R, Sorrentino R, Ianaro A, Bucci M, Esposito F, Cirino G. Crucial role of androgen receptor in vascular H2S biosynthesis induced by testosterone. Br J Pharmacol. 2015 Mar;172(6):1505-15. doi: 10.1111/bph.12740. Epub 2014 Jul 2. PMID: 24750035; PMCID: PMC4369260. 2. Chang CY, Hsuuw YD, Huang FJ, Shyr CR, Chang SY, Huang CK, Kang HY, Huang KE. Androgenic and antiandrogenic effects and expression of androgen receptor in mouse embryonic stem cells. Fertil Steril. 2006 Apr;85 Suppl 1:1195-203. doi: 10.1016/j.fertnstert.2005.11.031. PMID: 16616092. 3. Horsmans Y, Lannes D, Larrey D, Tinel M, Letteron P, Loeper J, Pessayre D. Nilutamide inhibits mephenytoin 4-hydroxylation in untreated male rats and in human liver microsomes. Xenobiotica. 1991 Dec;21(12):1559-70. doi: 10.3109/00498259109044405. PMID: 1785203. 4. Babany G, Tinel M, Letteron P, Freneaux E, Berson A, Larrey D, Pessayre D. Inhibitory effects of nilutamide, a new androgen receptor antagonist, on mouse and human liver cytochrome P-450. Biochem Pharmacol. 1989 Mar 15;38(6):941-7. doi: 10.1016/0006-2952(89)90284-0. PMID: 2930595.

In vitro protocol:

In vivo protocol:

1. Horsmans Y, Lannes D, Larrey D, Tinel M, Letteron P, Loeper J, Pessayre D. Nilutamide inhibits mephenytoin 4-hydroxylation in untreated male rats and in human liver microsomes. Xenobiotica. 1991 Dec;21(12):1559-70. doi: 10.3109/00498259109044405. PMID: 1785203. 2. Babany G, Tinel M, Letteron P, Freneaux E, Berson A, Larrey D, Pessayre D. Inhibitory effects of nilutamide, a new androgen receptor antagonist, on mouse and human liver cytochrome P-450. Biochem Pharmacol. 1989 Mar 15;38(6):941-7. doi: 10.1016/0006-2952(89)90284-0. PMID: 2930595.

1: Norlin M, Pettersson H, Tang W, Wikvall K. Androgen receptor-mediated regulation of the anti-atherogenic enzyme CYP27A1 involves the JNK/c-jun pathway. Arch Biochem Biophys. 2010 Dec 4. [Epub ahead of print] PubMed PMID: 21134350. 2: Akaza H. Combined androgen blockade for prostate cancer: review of efficacy, safety and cost-effectiveness. Cancer Sci. 2011 Jan;102(1):51-6. doi: 10.1111/j.1349-7006.2010.01774.x. Epub 2010 Nov 22. PubMed PMID: 21091846. 3: Foster WR, Car BD, Shi H, Levesque PC, Obermeier MT, Gan J, Arezzo JC, Powlin SS, Dinchuk JE, Balog A, Salvati ME, Attar RM, Gottardis MM. Drug safety is a barrier to the discovery and development of new androgen receptor antagonists. Prostate. 2010 Sep 28. [Epub ahead of print] PubMed PMID: 20878947. 4: Pavone-Macaluso M. Words of wisdom. Re: Does oral antiandrogen use before leuteinizing hormone-releasing therapy in patients with metastatic prostate cancer prevent clinical consequences of a testosterone flare? Oh WK, Landrum MB, Lamont EB, et al. Urology 2010;75:642-7. Eur Urol. 2010 Aug;58(2):314-5. PubMed PMID: 20845534. 5: Keiser J, Vargas M, Vennerstrom JL. Activity of antiandrogens against juvenile and adult Schistosoma mansoni in mice. J Antimicrob Chemother. 2010 Sep;65(9):1991-5. Epub 2010 Jun 24. PubMed PMID: 20576641; PubMed Central PMCID: PMC2920177. 6: Labrie F. Hormonal therapy of prostate cancer. Prog Brain Res. 2010;182:321-41. PubMed PMID: 20541672. 7: Koizumi H, Yu J, Hashimoto R, Ouchi Y, Okabe T. Involvement of androgen receptor in nitric oxide production induced by icariin in human umbilical vein endothelial cells. FEBS Lett. 2010 Jun 3;584(11):2440-4. Epub 2010 Apr 21. PubMed PMID: 20416296. 8: Yu J, Akishita M, Eto M, Ogawa S, Son BK, Kato S, Ouchi Y, Okabe T. Androgen receptor-dependent activation of endothelial nitric oxide synthase in vascular endothelial cells: role of phosphatidylinositol 3-kinase/akt pathway. Endocrinology. 2010 Apr;151(4):1822-8. Epub 2010 Mar 1. PubMed PMID: 20194727. 9: Langenhuijsen JF, van Lin EN, Hoffmann AL, Spitters-Post I, Alfred Witjes J, Kaanders JH, Mulders PF. Neoadjuvant androgen deprivation for prostate volume reduction: The optimal duration in prostate cancer radiotherapy. Urol Oncol. 2011 Jan-Feb;29(1):52-7. Epub 2009 Jun 12. PubMed PMID: 19523856. 10: Choo R, Danjoux C, Gardner S, Morton G, Szumacher E, Loblaw DA, Cheung P, Pearse M. Efficacy of salvage radiotherapy plus 2-year androgen suppression for postradical prostatectomy patients with PSA relapse. Int J Radiat Oncol Biol Phys. 2009 Nov 15;75(4):983-9. Epub 2009 May 4. PubMed PMID: 19409726.