Nafoxidine

Nafoxidine
ファイル:Nafoxidine.svg
Systematic (IUPAC) name
	1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine
Clinical data
Pregnancy cat.	?
Legal status	?
Routes	By mouth
Identifiers
CAS number	1845-11-0
ATC code	None
PubChem	CID 4416
IUPHAR ligand	4263
ChemSpider	4263
UNII	4RIY10WM82
KEGG	C14212
ChEBI	CHEBI:34881
ChEMBL	CHEMBL28211
Synonyms	U-11,000A; NSC-70735
Chemical data
Formula	C29H31NO2
	InChI InChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3; Key:JEYWNNAZDLFBFF-UHFFFAOYSA-N;

Nafoxidine (INNTooltip International Nonproprietary Name; developmental code names U-11,000A) or nafoxidine hydrochloride (USANTooltip United States Adopted Name) is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed.^[1]^[2]^[3] It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives.^[2] The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer.^[4] Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective.^[5]^[6] However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients,^[5] and this resulted in the discontinuation of its development.^[4]^[7]

Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more.^[8]

テンプレート:Comparison of early clinical experience with antiestrogens for advanced breast cancer

References

↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 848–. ISBN 978-1-4757-2085-3.
↑ ^{以下の位置に戻る: 2.0} ^2.1 Craig JV, Furr BJ (5 February 2010). Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. pp. 95–96. ISBN 978-1-59259-152-7.
↑ Weber GF (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 361–. ISBN 978-3-319-13278-5.
↑ ^{以下の位置に戻る: 4.0} ^4.1 McDaniel RE, Maximov PY, Jordan VC (2013). "Estrogen-mediated mechanisms to control the growth and apoptosis of breast cancer cells: a translational research success story". Vitamins and Hormones. 93: 1–49. doi:10.1016/B978-0-12-416673-8.00007-1. PMID 23810002.
↑ ^{以下の位置に戻る: 5.0} ^5.1 Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J (January 2017). "The use of high-dose estrogens for the treatment of breast cancer". Maturitas. 95: 11–23. doi:10.1016/j.maturitas.2016.10.010. PMID 27889048.
↑ Steinbaum FL, De Jager RL, Krakoff IH (1978). "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology. 4 (2): 123–126. doi:10.1002/mpo.2950040207. PMID 661750.
↑ Lupulescu A (24 October 1990). Hormones and Vitamins in Cancer Treatment. CRC Press. pp. 95–. ISBN 978-0-8493-5973-6.
↑ Hammond CB, Maxson WS (January 1982). "Current status of estrogen therapy for the menopause". Fertility and Sterility. 37 (1): 5–25. doi:10.1016/S0015-0282(16)45970-4. PMID 6277697.

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 848–. ISBN 978-1-4757-2085-3.

[CRAIGFurr2010-2] {以下の位置に戻る: 2.0} ^2.1 Craig JV, Furr BJ (5 February 2010). Hormone Therapy in Breast and Prostate Cancer. Springer Science & Business Media. pp. 95–96. ISBN 978-1-59259-152-7.

[Weber2015-3] Weber GF (22 July 2015). Molecular Therapies of Cancer. Springer. pp. 361–. ISBN 978-3-319-13278-5.

[Elsevier2013-4] {以下の位置に戻る: 4.0} ^4.1 McDaniel RE, Maximov PY, Jordan VC (2013). "Estrogen-mediated mechanisms to control the growth and apoptosis of breast cancer cells: a translational research success story". Vitamins and Hormones. 93: 1–49. doi:10.1016/B978-0-12-416673-8.00007-1. PMID 23810002.

[pmid27889048-5] {以下の位置に戻る: 5.0} ^5.1 Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J (January 2017). "The use of high-dose estrogens for the treatment of breast cancer". Maturitas. 95: 11–23. doi:10.1016/j.maturitas.2016.10.010. PMID 27889048.

[Steinbaumde_Jager1978-6] Steinbaum FL, De Jager RL, Krakoff IH (1978). "Clinical trial of nafoxidine in advanced breast cancer". Medical and Pediatric Oncology. 4 (2): 123–126. doi:10.1002/mpo.2950040207. PMID 661750.

[Lupulescu1990-7] Lupulescu A (24 October 1990). Hormones and Vitamins in Cancer Treatment. CRC Press. pp. 95–. ISBN 978-0-8493-5973-6.

[WallachHammond1982-8] Hammond CB, Maxson WS (January 1982). "Current status of estrogen therapy for the menopause". Fertility and Sterility. 37 (1): 5–25. doi:10.1016/S0015-0282(16)45970-4. PMID 6277697.

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Nafoxidine

References

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