Nafoxidine HCl | CAS#1847-63-8 | estrogen antagonist

MedKoo Cat#: 206550 | Name: Nafoxidine HCl

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Description:

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

Nafoxidine, also known as PNU-0011100 and CP-5600, is a partial estrogen antagonist. Nafoxidine competes with endogenous estrogen for binding to specific estrogen receptors. This agent also inhibits angiogenesis in some tissues by blocking the effects of fibroblast growth factor (FGF) and vascular endothelial growth factor (VEGF); paradoxically, it may enhance angiogenesis in uterine tissue. Nafoxidine also induces oxidative stress, protein kinase C and calcium signaling.

Chemical Structure

Nafoxidine HCl

CAS#1847-63-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 206550

Name: Nafoxidine HCl

CAS#: 1847-63-8 (HCl)

Chemical Formula: C29H32ClNO2

Exact Mass: 461.2122

Molecular Weight: 462.03

Elemental Analysis: C, 75.39; H, 6.98; Cl, 7.67; N, 3.03; O, 6.93

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 285.00	2 Weeks
25mg	USD 820.00	2 Weeks

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Related CAS #

1847-63-8 (HCl salt) 1845-11-0 (free base)

Synonym

CP-5600; CP5600; CP 5600; PNU-0011100; PNU 0011100; PNU0011100; U-11,000A; Nafoxidine HCl; Nafoxidine Hydrochloride;

IUPAC/Chemical Name

1-[2-[4-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl)phenoxy]ethyl]-pyrrolidine hydrochloride,

InChi Key

HJOOGTROABIIIU-UHFFFAOYSA-N

InChi Code

InChI=1S/C29H31NO2.ClH/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;1H

SMILES Code

COC1=CC2=C(C(C3=CC=C(OCCN4CCCC4)C=C3)=C(C5=CC=CC=C5)CC2)C=C1.[H]Cl

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nafoxidine, also known as PNU-0011100 and CP-5600, is a partial estrogen antagonist.

In vitro activity:

This study analyzed the effect of nafoxidine on the earlier biological processes of angiogenesis and explored the role of different signaling pathways involved in the in vitro response of endothelial cells (HUVEC). Nafoxidine significantly inhibited adhesion, spreading, migration and invasion of HUVEC at concentrations ranging from 1 to 2.5 microM. Endothelial cord formation on Matrigel was inhibited by nafoxidine and cotreatment with phorbol-12-myristate-13-acetate (PMA) clearly prevented the antiangiogenic effect of the antiestrogen. Reference: Anticancer Res. 2004 May-Jun;24(3a):1737-43. https://pubmed.ncbi.nlm.nih.gov/15274349/

In vivo activity:

Nafoxidine an antiestrogen is shown to possess antitumor activity against the Zajdela ascitic hepatoma. Nafoxidine prolonged the survival time of the rats injected with the tumor cells; complete regression of the tumor was observed when rats bearing a 3-day-old tumor were injected with this compound. Reference: Eur J Cancer Clin Oncol. 1986 Dec;22(12):1475-8. https://pubmed.ncbi.nlm.nih.gov/3595673/

Preparing Stock Solutions

The following data is based on the product molecular weight 462.03 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. 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. PMID: 15274349. 2. De Lorenzo MS, Alonso DF, Gomez DE. Nafoxidine modulates the expression of matrix-metalloproteinase-2 (MMP-2) and tissue inhibitor of metalloproteinases-1 (TIMP-1) in endothelial cells. Anticancer Res. 2000 Jan-Feb;20(1A):395-400. PMID: 10769686. 3. Khar A. Nafoxidine possesses antitumor activity against an ascitic hepatoma. Eur J Cancer Clin Oncol. 1986 Dec;22(12):1475-8. doi: 10.1016/0277-5379(86)90082-9. PMID: 3595673. 4. Strum JM. Nafoxidine administered to newborn female GR mice arrests the development of their mammary glands. Virchows Arch B Cell Pathol Incl Mol Pathol. 1983;42(2):227-33. doi: 10.1007/BF02890385. PMID: 6133394.

In vitro protocol:

In vivo protocol:

1. Khar A. Nafoxidine possesses antitumor activity against an ascitic hepatoma. Eur J Cancer Clin Oncol. 1986 Dec;22(12):1475-8. doi: 10.1016/0277-5379(86)90082-9. PMID: 3595673. 2. Strum JM. Nafoxidine administered to newborn female GR mice arrests the development of their mammary glands. Virchows Arch B Cell Pathol Incl Mol Pathol. 1983;42(2):227-33. doi: 10.1007/BF02890385. PMID: 6133394.

1: 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. 2: 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. 3: 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. 4: De Lorenzo MS, Alonso DF, Gomez DE. Nafoxidine modulates the expression of matrix-metalloproteinase-2 (MMP-2) and tissue inhibitor of metalloproteinases-1 (TIMP-1) in endothelial cells. Anticancer Res. 2000 Jan-Feb;20(1A):395-400. PubMed PMID: 10769686. 5: 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. 6: Fanidi A, Courion-Guichardaz C, Fayard JM, Pageaux JF, Laugier C. Effects of tamoxifen, tamoxifen metabolites, and nafoxidine on adenosine 3',5'-monophosphate phosphodiesterase: correlations with growth inhibitory activities but not estrogen receptor affinities. Endocrinology. 1989 Sep;125(3):1187-93. PubMed PMID: 2547579. 7: Quarmby VE, Fox-Davies C, Newbold RR, Korach KS. Response of the mouse uterus to nafoxidine stimulation: agonism and antagonism. Biol Reprod. 1988 May;38(4):945-54. PubMed PMID: 3401548. 8: 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. 9: Khar A. Nafoxidine possesses antitumor activity against an ascitic hepatoma. Eur J Cancer Clin Oncol. 1986 Dec;22(12):1475-8. PubMed PMID: 3595673. 10: Galand P, Tchernitchin N, Tchernitchin AN. Dissociation of uterine eosinophilia and water imbibition from other estrogen-induced responses by nafoxidine pretreatment. Mol Cell Endocrinol. 1985 Oct;42(3):227-33. PubMed PMID: 2412910. 11: Trachtenberg J. Androgen receptor content of nafoxidine treated experimentally induced canine prostatic hyperplasia. Clin Invest Med. 1985;8(1):29-34. PubMed PMID: 2580656. 12: 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. 13: Galand P, Mairesse N, Roorijck J, Flandroy L. Differential blockade of estrogen-induced uterine responses by the antiestrogen nafoxidine. J Steroid Biochem. 1983 Sep;19(3):1259-63. PubMed PMID: 6194375. 14: Strum JM. Nafoxidine administered to newborn female GR mice arrests the development of their mammary glands. Virchows Arch B Cell Pathol Incl Mol Pathol. 1983;42(2):227-33. PubMed PMID: 6133394. 15: Sala Blanco J, Casas Tineo B, Hidalgo A. [Effects of subacute treatment with clomiphene, ethamoxytriphetol (Mer-25), and nafoxidine on blood calcium and bone density in rats]. Rev Esp Oncol. 1982;29(3):497-503. Spanish. PubMed PMID: 6927021. 16: 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. 17: 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. 18: Mairesse N, Reiss N, Galand P, Kaye AM. Nafoxidine-responsive uterine protein: further characterization and distinction from the "estrogen-induced" protein (IP). Mol Cell Endocrinol. 1981 Oct;24(1):53-63. PubMed PMID: 6173271. 19: Hamburger AD. Effects of nafoxidine and oestriol on the oestradiol-induced activation of rat liver tryptophan oxygenase and tyrosine aminotransferase and increase in uterine weight. Biochem Pharmacol. 1981 Sep 1;30(17):2485-8. PubMed PMID: 21043251. 20: Stolbach LL, Begg CB, Hall T, Horton J. Treatment of renal carcinoma: a phase III randomized trial of oral medroxyprogesterone (Provera), hydroxyurea, and nafoxidine. Cancer Treat Rep. 1981 Jul-Aug;65(7-8):689-92. PubMed PMID: 6454485.

View History

NSC-77053

MedKoo CAT#: 561194

CAS#: 77308-57-7