Bicalutamide

  • CAT Number: A000982
  • CAS Number: 90357-06-5
  • Molecular Formula: C18H14F4N2O4S
  • Molecular Weight: 430.4
  • Purity: ≥95%
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Bicalutamide is a synthetic, nonsteroidal antiandrogen. Bicalutamide competitively binds to cytosolic androgen receptors in target tissues, thereby inhibiting the receptor binding of androgens. This agent does not bind to most mutated forms of androgen receptors.

Catalog Number A000982
CAS Number 90357-06-5
Molecular Formula

C18H14F4N2O4S

Purity 95%
Target Androgen Receptor
Solubility >21.5mg/mL in DMSO
Storage -20°C
InChI 1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
InChIKey LKJPYSCBVHEWIU-UHFFFAOYSA-N
SMILES CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
Reference

1: Moretti C, Guccione L, Di Giacinto P, Simonelli I, Exacoustos C, Toscano V,
Motta C, De Leo V, Petraglia F, Lenzi A. Combined Oral Contraception and
Bicalutamide in Polycystic Ovary Syndrome and Severe Hirsutism – a Double-blind
RTC. J Clin Endocrinol Metab. 2017 Dec 1. doi: 10.1210/jc.2017-01186. [Epub ahead
of print] PubMed PMID: 29211888.
<br>

2: Huang R, Han J, Liang X, Sun S, Jiang Y, Xia B, Niu M, Li D, Zhang J, Wang S,
Wei W, Liu Q, Zheng W, Zhang G, Song Y, Panga D. Androgen Receptor Expression and
Bicalutamide Antagonize Androgen Receptor Inhibit β-Catenin Transcription Complex
in Estrogen Receptor-Negative Breast Cancer. Cell Physiol Biochem.
2017;43(6):2212-2225. doi: 10.1159/000484300. Epub 2017 Oct 25. PubMed PMID:
29069648.
<br>

3: de Jesus Cortez F, Nguyen P, Truillet C, Tian B, Kuchenbecker KM, Evans MJ,
Webb P, Jacobson MP, Fletterick RJ, England PM. Development of 5N-Bicalutamide, a
High-Affinity Reversible Covalent Antiandrogen. ACS Chem Biol. 2017 Dec
15;12(12):2934-2939. doi: 10.1021/acschembio.7b00702. Epub 2017 Nov 2. PubMed
PMID: 28981251.
<br>

4: Bulldan A, Malviya VN, Upmanyu N, Konrad L, Scheiner-Bobis G.
Testosterone/bicalutamide antagonism at the predicted extracellular androgen
binding site of ZIP9. Biochim Biophys Acta. 2017 Dec;1864(12):2402-2414. doi:
10.1016/j.bbamcr.2017.09.012. Epub 2017 Sep 21. PubMed PMID: 28943399.
<br>

5: Wang Y, Jiang W, Huo C. One-Pot Synthesis of β-Hydroxysulfones and Its
Application in the Preparation of Anticancer Drug Bicalutamide. J Org Chem. 2017
Oct 6;82(19):10628-10634. doi: 10.1021/acs.joc.7b01371. Epub 2017 Sep 14. PubMed
PMID: 28875700.
<br>

6: Siemens DR, Klotz L, Heidenreich A, Chowdhury S, Villers A, Baron B, van Os S,
Hasabou N, Wang F, Lin P, Shore ND. Efficacy and Safety of Enzalutamide vs
Bicalutamide in Younger and Older Patients with Metastatic Castration Resistant
Prostate Cancer in the TERRAIN Trial. J Urol. 2017 Aug 19. pii:
S0022-5347(17)77377-6. doi: 10.1016/j.juro.2017.08.080. [Epub ahead of print]
PubMed PMID: 28827103.
<br>

7: Rams-Baron M, Wlodarczyk P, Dulski M, Wlodarczyk A, Kruk D, Rachocki A,
Jachowicz R, Paluch M. The indications of tautomeric conversion in amorphous
bicalutamide drug. Eur J Pharm Sci. 2017 Dec 15;110:117-123. doi:
10.1016/j.ejps.2017.06.034. Epub 2017 Jun 28. PubMed PMID: 28666849.

<br>
8: Pilon D, Behl AS, Ellis LA, Robitaille MN, Lefebvre P, Dawson NA. Assessment
of Real-World Central Nervous System Events in Patients with Advanced Prostate
Cancer Using Abiraterone Acetate, Bicalutamide, Enzalutamide, or Chemotherapy. Am
Health Drug Benefits. 2017 May;10(3):143-153. PubMed PMID: 28626511; PubMed
Central PMCID: PMC5470240.
<br>

9: Yang C, Di P, Fu J, Xiong H, Jing Q, Ren G, Tang Y, Zheng W, Liu G, Ren F.
Improving the physicochemical properties of bicalutamide by complex formation
with bovine serum albumin. Eur J Pharm Sci. 2017 Aug 30;106:381-392. doi:
10.1016/j.ejps.2017.05.059. Epub 2017 May 29. PubMed PMID: 28571783.

<br>
10: Sakamoto K, Ito T, Tanioka F, Fukamizu H, Tokura Y. Primary signet-ring
cell/histiocytoid carcinoma of the eyelid expressing androgen receptors and
treated with bicalutamide. J Dermatol. 2017 Sep;44(9):e230-e231. doi:
10.1111/1346-8138.13915. Epub 2017 May 23. PubMed PMID: 28543368.

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