Nafoxidine

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

MedKoo CAT#: 584883

CAS#: 1845-11-0

Description: Nafoxidine is an estrogen antagonist that has been used in the treatment of breast cancer.


Price and Availability

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Nafoxidine is not in stock, 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#: 584883
Name: Nafoxidine
CAS#: 1845-11-0
Chemical Formula: C29H31NO2
Exact Mass: 425.2355
Molecular Weight: 425.572
Elemental Analysis: C, 81.85; H, 7.34; N, 3.29; O, 7.52


Synonym: Nafoxidine

IUPAC/Chemical Name: Pyrrolidine, 1-(2-(4-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl)phenoxy)ethyl)-

InChi Key: JEYWNNAZDLFBFF-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: COC1=CC2=C(C(C3=CC=C(OCCN4CCCC4)C=C3)=C(C5=CC=CC=C5)CC2)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

Shelf Life:
>3 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:
2934990300


References

1: Johansson Seechurn CCC, Gazić Smilović I, Colacot T, Zanotti-Gerosa A, Časar Z. Development of concise two-step catalytic approach towards lasofoxifene precursor nafoxidine. Bioorg Med Chem. 2018 May 15;26(9):2691-2697. doi: 10.1016/j.bmc.2018.04.021. Epub 2018 Apr 10. PubMed PMID: 29678534.

2: Bloom HJ, Boesen E. Antioestrogens in treatment of breast cancer: value of nafoxidine in 52 advanced cases. Br Med J. 1974 Apr 6;2(5909):7-10. PubMed PMID: 4362455; PubMed Central PMCID: PMC1610174.

3: Sato M, Rippy MK, Bryant HU. Raloxifene, tamoxifen, nafoxidine, or estrogen effects on reproductive and nonreproductive tissues in ovariectomized rats. FASEB J. 1996 Jun;10(8):905-12. PubMed PMID: 8666168.

4: Lazier CB, Alford WS. Interaction of the anti-oestrogen, nafoxidine hydrochloride, with the soluble nuclear oestradiol-binding protein in chick liver. Biochem J. 1977 Jun 15;164(3):659-67. PubMed PMID: 883957; PubMed Central PMCID: PMC1164844.

5: Attardi B, Palumbo LA. Effects of nafoxidine on the luteinizing hormone surge: temporal distribution of estrogen receptors and induction of cytoplasmic progestin receptors in the hypothalamus-preoptic area, pituitary, and uterus of the immature rat. Endocrinology. 1981 Nov;109(5):1365-74. PubMed PMID: 7297482.

6: Sasaki GH, Leung BS, Fletcher WS. Therapeutic value of nafoxidine hydrochloride in the treatment of advanced carcinoma of the human breast. Surg Gynecol Obstet. 1976 Apr;142(4):560-4. PubMed PMID: 1257870.

7: Devi PK. Antiestrogens. Pharmacol Ther. 1981;12(3):439-47. Review. PubMed PMID: 7025028.

8: Maertens C, Droogmans G, Chakraborty P, Nilius B. Inhibition of volume-regulated anion channels in cultured endothelial cells by the anti-oestrogens clomiphene and nafoxidine. Br J Pharmacol. 2001 Jan;132(1):135-42. PubMed PMID: 11156570; PubMed Central PMCID: PMC1572544.

9: Campbell PS, Satterfield PM. Effect of neonatal exposure to the antioestrogens nafoxidine and CI-628 upon the development of the uterus in the prepubertal rat. J Reprod Fertil. 1988 May;83(1):225-31. PubMed PMID: 3397940.

10: Santa Cruz AR, Medrano EE, Baldi A. Dolichol-sugar derivative synthesis in human breast cancer cell line (T47D). Effects of estrogens and antiestrogens. Biochem Biophys Res Commun. 1985 Jan 16;126(1):382-8. PubMed PMID: 3970700.

11: De Lorenzo MS, Farina HG, Alonso DF, Gomez DE. Role of protein kinase C-dependent signaling pathways in the antiangiogenic properties of nafoxidine. Anticancer Res. 2004 May-Jun;24(3a):1737-43. PubMed PMID: 15274349.

12: Gray JM, Wade GN. Food intake, body weight, and adiposity in female rats: actions and interactions of progestins and antiestrogens. Am J Physiol. 1981 May;240(5):E474-81. PubMed PMID: 7195153.

13: Yaz G, Kabadere S, Oztopçu P, Durmaz R, Uyar R. Comparison of the antiproliferative properties of antiestrogenic drugs (nafoxidine and clomiphene) on glioma cells in vitro. Am J Clin Oncol. 2004 Aug;27(4):384-8. PubMed PMID: 15289732.

14: Galand P, Tchernitchin N, Tchernitchin AN. Time-course of the effects of nafoxidine and oestradiol on separate groups of responses in the uterus of the immature rat. J Steroid Biochem. 1984 Jul;21(1):43-7. PubMed PMID: 6748655.

15: Alhadi T, Vonderhaar BK. Induction of cryptic lactogenic hormone binding in livers of adult female mice treated neonatally with estradiol or nafoxidine. Endocrinology. 1982 Jan;110(1):254-9. PubMed PMID: 6274621.

16: Trachtenberg J. Androgen receptor content of nafoxidine treated experimentally induced canine prostatic hyperplasia. Clin Invest Med. 1985;8(1):29-34. PubMed PMID: 2580656.

17: Chan L, Jackson RL, Means AR. Female steroid hormones and lipoprotein synthesis in the cockerel: effects of progesterone and nafoxidine on the estrogenic stimulation of very low density lipoproteins (VLDL) synthesis. Endocrinology. 1977 Jun;100(6):1636-43. PubMed PMID: 192542.

18: Gardner RM, Kirkland JL, Stancel GM. Selective blockade of estrogen-induced uterine responses by the antiestrogen nafoxidine. Endocrinology. 1978 Nov;103(5):1583-9. PubMed PMID: 748005.

19: Wiseman H. The antioxidant action of a pure antioestrogen: ability to inhibit lipid peroxidation compared to tamoxifen and 17 beta-oestradiol and relevance to its anticancer potential. Biochem Pharmacol. 1994 Feb 9;47(3):493-8. PubMed PMID: 8117317.

20: Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. PubMed PMID: 9048584.