Fadrozole free base

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

MedKoo CAT#: 205962

CAS#: 102676-47-1 (free base)

Description: Fadrozole is a nonsteroidal aromatase inhibitor with potential antineoplastic activity. Fadrozole specifically inhibits aromatase, blocking the aromatization of androstenedione and testosterone into estrone and estradiol, respectively, the final step in estrogen biosynthesis; the reduction in estrogen levels may inhibit growth in estrogen-dependent cancers. Aromatase, a member of the cytochrome P-450 superfamily, is found in many tissues; overexpression has been linked to the development of preneoplastic and neoplastic changes in breast tissue. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

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Fadrozole is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205962
Name: Fadrozole free base
CAS#: 102676-47-1 (free base)
Chemical Formula: C14H13N3
Exact Mass: 223.11095
Molecular Weight: 223.27
Elemental Analysis: C, 75.31; H, 5.87; N, 18.82


Related CAS #: 102676-31-3 (HCl)   176702-70-8 (HCl hydrate)   102676-47-1 (free base)    

Synonym: Fadrozole; CGS 16949A; CGS-16949A; CGS16949A; Fadrozole free base

IUPAC/Chemical Name: 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile

InChi Key: CLPFFLWZZBQMAO-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H13N3/c15-8-11-4-6-12(7-5-11)14-3-1-2-13-9-16-10-17(13)14/h4-7,9-10,14H,1-3H2

SMILES Code: N#CC1=CC=C(C2CCCC3=CN=CN23)C=C1


Technical Data

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:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Brixius-Anderko S, Scott EE. Structure of human cortisol-producing cytochrome P450 11B1 bound to the breast cancer drug fadrozole provides insights for drug design. J Biol Chem. 2018 Nov 13. pii: jbc.RA118.006214. doi: 10.1074/jbc.RA118.006214. [Epub ahead of print] PubMed PMID: 30425102.

2: Hajihoseini Z, Eghbalsaied S. Simultaneous effects of IGF1 and Fadrozole on parthenogenesis and pluripotency markers in chicken embryo. Theriogenology. 2018 Jul 1;114:317-323. doi: 10.1016/j.theriogenology.2018.04.009. Epub 2018 Apr 13. PubMed PMID: 29684809.

3: Schroeder AL, Ankley GT, Habib T, Garcia-Reyero N, Escalon BL, Jensen KM, Kahl MD, Durhan EJ, Makynen EA, Cavallin JE, Martinovic-Weigelt D, Perkins EJ, Villeneuve DL. Rapid effects of the aromatase inhibitor fadrozole on steroid production and gene expression in the ovary of female fathead minnows (Pimephales promelas). Gen Comp Endocrinol. 2017 Oct 1;252:79-87. doi: 10.1016/j.ygcen.2017.07.022. Epub 2017 Jul 21. PubMed PMID: 28736226; PubMed Central PMCID: PMC6010346.

4: Luzio A, Matos M, Santos D, Fontaínhas-Fernandes AA, Monteiro SM, Coimbra AM. Disruption of apoptosis pathways involved in zebrafish gonad differentiation by 17α-ethinylestradiol and fadrozole exposures. Aquat Toxicol. 2016 Aug;177:269-84. doi: 10.1016/j.aquatox.2016.05.029. Epub 2016 Jun 3. PubMed PMID: 27337697.

5: Luzio A, Monteiro SM, Rocha E, Fontaínhas-Fernandes AA, Coimbra AM. Development and recovery of histopathological alterations in the gonads of zebrafish (Danio rerio) after single and combined exposure to endocrine disruptors (17α-ethinylestradiol and fadrozole). Aquat Toxicol. 2016 Jun;175:90-105. doi: 10.1016/j.aquatox.2016.03.014. Epub 2016 Mar 16. PubMed PMID: 27002526.

6: Luzio A, Monteiro SM, Garcia-Santos S, Rocha E, Fontaínhas-Fernandes AA, Coimbra AM. Zebrafish sex differentiation and gonad development after exposure to 17α-ethinylestradiol, fadrozole and their binary mixture: A stereological study. Aquat Toxicol. 2015 Sep;166:83-95. doi: 10.1016/j.aquatox.2015.07.015. Epub 2015 Jul 26. PubMed PMID: 26240953.

7: Mohammadrezaei M, Toghyani M, Gheisari A, Toghyani M, Eghbalsaied S. Synergistic effect of fadrozole and insulin-like growth factor-I on female-to-male sex reversal and body weight of broiler chicks. PLoS One. 2014 Jul 30;9(7):e103570. doi: 10.1371/journal.pone.0103570. eCollection 2014. PubMed PMID: 25075864; PubMed Central PMCID: PMC4116201.

8: Leonard JA, Cope WG, Barnhart MC, Bringolf RB. Metabolomic, behavioral, and reproductive effects of the aromatase inhibitor fadrozole hydrochloride on the unionid mussel Lampsilis fasciola. Gen Comp Endocrinol. 2014 Sep 15;206:213-26. doi: 10.1016/j.ygcen.2014.07.019. Epub 2014 Jul 27. PubMed PMID: 25072892.

9: Shanthanagouda AH, Nugegoda D, Patil JG. Effects of bisphenol A and fadrozole exposures on cyp19a1 expression in the Murray rainbowfish, Melanotaenia fluviatilis. Arch Environ Contam Toxicol. 2014 Aug;67(2):270-80. doi: 10.1007/s00244-014-0047-1. Epub 2014 Jun 5. PubMed PMID: 24898176.

10: Duarte-Guterman P, Langlois VS, Hodgkinson K, Pauli BD, Cooke GM, Wade MG, Trudeau VL. The aromatase inhibitor fadrozole and the 5-reductase inhibitor finasteride affect gonadal differentiation and gene expression in the frog Silurana tropicalis. Sex Dev. 2009;3(6):333-41. doi: 10.1159/000280586. Epub 2010 Feb 2. PubMed PMID: 20130388.

11: Langlois VS, Duarte-Guterman P, Ing S, Pauli BD, Cooke GM, Trudeau VL. Fadrozole and finasteride exposures modulate sex steroid- and thyroid hormone-related gene expression in Silurana (Xenopus) tropicalis early larval development. Gen Comp Endocrinol. 2010 Apr 1;166(2):417-27. doi: 10.1016/j.ygcen.2009.11.004. Epub 2009 Nov 14. PubMed PMID: 19917284.

12: Zhang D, Popesku JT, Martyniuk CJ, Xiong H, Duarte-Guterman P, Yao L, Xia X, Trudeau VL. Profiling neuroendocrine gene expression changes following fadrozole-induced estrogen decline in the female goldfish. Physiol Genomics. 2009 Aug 7;38(3):351-61. doi: 10.1152/physiolgenomics.00051.2009. Epub 2009 Jun 9. PubMed PMID: 19509080.

13: Villeneuve L, Wang RL, Bencic DC, Biales AD, Martinović D, Lazorchak JM, Toth G, Ankley GT. Altered gene expression in the brain and ovaries of zebrafish (Danio rerio) exposed to the aromatase inhibitor fadrozole: microarray analysis and hypothesis generation. Environ Toxicol Chem. 2009 Aug;28(8):1767-82. doi: 10.1897/08-653.1. PubMed PMID: 19422270.

14: Zhang X, Hecker M, Park JW, Tompsett AR, Jones PD, Newsted J, Au DW, Kong R, Wu RS, Giesy JP. Time-dependent transcriptional profiles of genes of the hypothalamic-pituitary-gonadal axis in medaka (Oryzias latipes) exposed to fadrozole and 17beta-trenbolone. Environ Toxicol Chem. 2008 Dec;27(12):2504-11. doi: 10.1897/08-082.1. PubMed PMID: 18693774.

15: Wacker DW, Schlinger BA, Wingfield JC. Combined effects of DHEA and fadrozole on aggression and neural VIP immunoreactivity in the non-breeding male song sparrow. Horm Behav. 2008 Jan;53(1):287-94. Epub 2007 Oct 24. PubMed PMID: 18036596.

16: Minnaard-Huiban M, Emmen JM, Roumen L, Beugels IP, Cohuet GM, van Essen H, Ruijters E, Pieterse K, Hilbers PA, Ottenheijm HC, Plate R, de Gooyer ME, Smits JF, Hermans JJ. Fadrozole reverses cardiac fibrosis in spontaneously hypertensive heart failure rats: discordant enantioselectivity versus reduction of plasma aldosterone. Endocrinology. 2008 Jan;149(1):28-31. Epub 2007 Sep 20. PubMed PMID: 17884944.

17: Mikolajczyk T, Chyb J, Sokolowska-Mikolajczyk M, Szczerbik P, Socha M, Epler P. The effect of aromatase inhibitor, fadrozole, on sGnRHa stimulated LH secretion in goldfish (Carassius auratus) and common carp (Cyprinus carpio). Reprod Biol. 2006;6 Suppl 1:195-9. Review. PubMed PMID: 16967099.

18: Ménard J, Pascoe L. Can the dextroenantiomer of the aromatase inhibitor fadrozole be useful for clinical investigation of aldosterone-synthase inhibition? J Hypertens. 2006 Jun;24(6):993-7. Review. PubMed PMID: 16685193.

19: Tamada H, Shimizu Y, Inaba T, Kawate N, Sawada T. The effects of the aromatase inhibitor fadrozole hydrochloride on fetuses and uteri in late pregnant rats. J Endocrinol. 2004 Feb;180(2):337-45. PubMed PMID: 14765986.

20: Nunez SB, Calis K, Cutler GB Jr, Jones J, Feuillan PP. Lack of efficacy of fadrozole in treating precocious puberty in girls with the McCune-Albright syndrome. J Clin Endocrinol Metab. 2003 Dec;88(12):5730-3. PubMed PMID: 14671160.