Estramustine phosphate sodium
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MedKoo CAT#: 100310

CAS#: 52205-73-9 (phosphate sodium)

Description: Estramustine phosphate sodium is a synthetic molecule that combines estradiol and nornitrogen mustard through a carbamate link. Estramustine and its major metabolite estramustine bind to microtubule-associated proteins (MAPs) and tubulin, thereby inhibiting microtubule dynamics and leading to anaphase arrest in a dose-dependent fashion. This agent also exhibits anti-androgenic effects. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

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Estramustine phosphate sodium
CAS# 52205-73-9 (phosphate sodium)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100310
Name: Estramustine phosphate sodium
CAS#: 52205-73-9 (phosphate sodium)
Chemical Formula: C23H30Cl2NNa2O6P
Exact Mass: 0.00
Molecular Weight: 564.350
Elemental Analysis: C, 48.95; H, 5.36; Cl, 12.56; N, 2.48; Na, 8.15; O, 17.01; P, 5.49

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1550 Ready to ship
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Related CAS #: 2998-57-4 (free base)   4891-15-0 (phosphate)   52205-73-9 (phosphate sodium)  

Synonym: Ro 21-8837/001; Leo299; Ro 222296000; LS 299; NSC 89199; estramustine Phosphate sodium; Emcyt. Estracyt.

IUPAC/Chemical Name: sodium (8R,9S,13S,14S,17S)-3-((bis(2-chloroethyl)carbamoyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl phosphate

InChi Key: IIUMCNJTGSMNRO-VVSKJQCTSA-L

InChi Code: InChI=1S/C23H32Cl2NO6P.2Na/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30;;/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30);;/q;2*+1/p-2/t18-,19-,20+,21+,23+;;/m1../s1

SMILES Code: O=P([O-])([O-])O[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(OC(N(CCCl)CCCl)=O)=CC=C4[C@@]3([H])CC[C@]12C.[Na+].[Na+]

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

More Info:

Biological target: Estramustine phosphate sodium is an antimicrotubule chemotherapy agent.
In vitro activity: The molecular mechanism of estramustine phosphate in regulating PC3 cell growth was assessed. PC3 cell appeared growth restrain and apoptosis after treated by estramustine phosphate. MiR-31 level decreased after estramustine phosphate treatment. Prostate cancer tissue presented higher miR-31 level than paracarcinoma tissue. MiR-31 over-expression inhibited estramustine phosphate induced PC3 cell apoptosis. Reference: Eur Rev Med Pharmacol Sci. 2018 Jan;22(1):40-45. https://www.europeanreview.org/article/14098
In vivo activity: The effect of irradiation, alone and in combination with the antimicrotubule drug estramustine (EaM), was investigated in vivo using the BT4C rat intracerebral glioma model. Irradiation did not induce apoptosis in vivo. EaM, however, induced apoptosis in vivo, regardless of whether EaM was given alone, before or after irradiation. Reference: J Neurooncol. 2002 Jan;56(2):143-8. https://pubmed.ncbi.nlm.nih.gov/11995815/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 81.3 143.97
PBS (pH 7.2) 10.0 17.72
DMSO 1.8 3.10
DMF 0.3 0.44

Preparing Stock Solutions

The following data is based on the product molecular weight 564.35 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.

Recalculate based on batch purity %
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. Wei C, Pan Y, Huang H, Li YP. Estramustine phosphate induces prostate cancer cell line PC3 apoptosis by down-regulating miR-31 levels. Eur Rev Med Pharmacol Sci. 2018 Jan;22(1):40-45. doi: 10.26355/eurrev_201801_14098. PMID: 29364469. 2. Mojsilovic SS, Mojsilovic S, Bjelica S, Santibanez JF. Estramustine Phosphate Inhibits TGF-β-Induced Mouse Macrophage Migration and Urokinase-Type Plasminogen Activator Production. Anal Cell Pathol (Amst). 2018 Sep 2;2018:3134102. doi: 10.1155/2018/3134102. PMID: 30245956; PMCID: PMC6139214. 3. Vallbo C, Bergenheim T, Hedman H, Henriksson R. The antimicrotubule drug estramustine but not irradiation induces apoptosis in malignant glioma involving AKT and caspase pathways. J Neurooncol. 2002 Jan;56(2):143-8. doi: 10.1023/a:1014562503097. PMID: 11995815.
In vitro protocol: 1. Wei C, Pan Y, Huang H, Li YP. Estramustine phosphate induces prostate cancer cell line PC3 apoptosis by down-regulating miR-31 levels. Eur Rev Med Pharmacol Sci. 2018 Jan;22(1):40-45. doi: 10.26355/eurrev_201801_14098. PMID: 29364469. 2. Mojsilovic SS, Mojsilovic S, Bjelica S, Santibanez JF. Estramustine Phosphate Inhibits TGF-β-Induced Mouse Macrophage Migration and Urokinase-Type Plasminogen Activator Production. Anal Cell Pathol (Amst). 2018 Sep 2;2018:3134102. doi: 10.1155/2018/3134102. PMID: 30245956; PMCID: PMC6139214.
In vivo protocol: 1. Vallbo C, Bergenheim T, Hedman H, Henriksson R. The antimicrotubule drug estramustine but not irradiation induces apoptosis in malignant glioma involving AKT and caspase pathways. J Neurooncol. 2002 Jan;56(2):143-8. doi: 10.1023/a:1014562503097. PMID: 11995815.

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1: Song P, Huang C, Wang Y. The efficacy and safety comparison of docetaxel, cabazitaxel, estramustine, and mitoxantrone for castration-resistant prostate cancer: A network meta-analysis. Int J Surg. 2018 Jun 12. pii: S1743-9191(18)31502-4. doi: 10.1016/j.ijsu.2018.06.010. [Epub ahead of print] PubMed PMID: 29906643.

2: D'Aniello C, Pisconti S, Facchini S, Imbimbo C, Cavaliere C. Estramustine phosphate induces prostate cancer cell line PC3 apoptosis by down-regulating miR-31 levels. Eur Rev Med Pharmacol Sci. 2018 Apr;22(7):1875-1876. doi: 10.26355/eurrev_201804_14706. PubMed PMID: 29687836.

3: Lin X, Wang Y. Re-expression of microRNA-4319 inhibits growth of prostate cancer via Her-2 suppression. Clin Transl Oncol. 2018 Apr 9. doi: 10.1007/s12094-018-1871-y. [Epub ahead of print] PubMed PMID: 29633185.

4: Azuma T, Matayoshi Y, Sato Y, Nagase Y. Effect of dutasteride on castration-resistant prostate cancer. Mol Clin Oncol. 2018 Jan;8(1):133-136. doi: 10.3892/mco.2017.1480. Epub 2017 Nov 2. PubMed PMID: 29387405; PubMed Central PMCID: PMC5769310.

5: Wei C, Pan Y, Huang H, Li YP. Estramustine phosphate induces prostate cancer cell line PC3 apoptosis by down-regulating miR-31 levels. Eur Rev Med Pharmacol Sci. 2018 Jan;22(1):40-45. doi: 10.26355/eurrev_201801_14098. PubMed PMID: 29364469.

6: Goto M, Kitamura N, Tanaka A, Katsuragi T, Higashi T, Morimoto H, Shimajiri S, Tsukada J. [Primary breast diffuse large B-cell lymphoma developing subsequent to estramustine therapy for prostate cancer]. Rinsho Ketsueki. 2017;58(12):2411-2413. doi: 10.11406/rinketsu.58.2411. Japanese. PubMed PMID: 29332876.

7: Wong YN, Manola J, Hudes GR, Roth BJ, Moul JW, Barsevick AM, Scher RM, Volk MJ, Vaughn DJ, Williams SD, Fisch MJ, Cella D, Carducci MA, Wilding G. Phase 2 Study of Weekly Paclitaxel Plus Estramustine in Metastatic Hormone-Refractory Prostate Carcinoma: ECOG-ACRIN Cancer Research Group (E1898) Trial. Clin Genitourin Cancer. 2018 Apr;16(2):e315-e322. doi: 10.1016/j.clgc.2017.10.001. Epub 2017 Oct 16. PubMed PMID: 29173976; PubMed Central PMCID: PMC5975965.

8: Matsumoto T, Hatakeyama S, Ookubo T, Mitsuzuka K, Narita S, Inoue T, Yamashita S, Narita T, Koie T, Kawamura S, Tochigi T, Tsuchiya N, Habuchi T, Arai Y, Ohyama C. Cost-effectiveness comparison between neoadjuvant chemohormonal therapy and extended pelvic lymph node dissection in high-risk prostate cancer patients treated with radical prostatectomy: a multi-institutional analysis. Med Oncol. 2017 Oct 31;34(12):190. doi: 10.1007/s12032-017-1050-y. PubMed PMID: 29090390.

9: Patial V, Sharma S, Sk UH. Dendrimer conjugated estramustine nanocrystalline 'Dendot': An effective inhibitor of DMBA-TPA induced papilloma formation in mouse. Eur J Pharm Sci. 2017 Nov 15;109:316-323. doi: 10.1016/j.ejps.2017.08.026. Epub 2017 Aug 23. PubMed PMID: 28842350.

10: Fujita N, Koie T, Ohyama C, Tanaka Y, Soma O, Matsumoto T, Yamamoto H, Imai A, Tobisawa Y, Yoneyama T, Hatakeyama S, Hashimoto Y. Overall survival of high-risk prostate cancer patients who received neoadjuvant chemohormonal therapy followed by radical prostatectomy at a single institution. Int J Clin Oncol. 2017 Dec;22(6):1087-1093. doi: 10.1007/s10147-017-1160-8. Epub 2017 Jul 5. PubMed PMID: 28681153.

11: 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.

12: Fukui T, Nakamura K, Sakatani T, Atsuta T, Kato T, Fukumoto T, Ito M, Inoue K, Terai A. [Low-Dose Estramustine Phosphate Monotherapy in Castration-Resistant Prostate Cancer Patients]. Hinyokika Kiyo. 2017 Feb;63(2):57-62. doi: 10.14989/ActaUrolJap_63_2_57. Japanese. PubMed PMID: 28264534.

13: Hagiwara K, Koie T, Ohyama C, Yamamoto H, Imai A, Hatakeyama S, Yoneyama T, Hashimoto Y, Tobisawa Y, Yoneyama T. Efficacy of a neoadjuvant gonadotropin-releasing hormone antagonist plus low-dose estramustine phosphate in high-risk prostate cancer: a single-center study. Int Urol Nephrol. 2017 May;49(5):811-816. doi: 10.1007/s11255-017-1546-6. Epub 2017 Feb 17. PubMed PMID: 28213801.

14: Kandori S, Yoshino T, Tsutsumi M, Yamauchi A, Ohtani M, Fukuhara Y, Miyanaga N, Miyazaki J, Nishiyama H, Shimazui T. Feasibility of classical secondary hormonal therapies prior to docetaxel therapy in Japanese patients with castration-resistant prostate cancer: Multicenter retrospective study. Prostate Int. 2016 Dec;4(4):140-144. Epub 2016 Sep 20. PubMed PMID: 27995113; PubMed Central PMCID: PMC5153431.

15: Narita T, Koie T, Ookubo T, Mitsuzuka K, Narita S, Yamamoto H, Inoue T, Hatakeyama S, Kawamura S, Tochigi T, Habuchi T, Arai Y, Ohyama C. The impact of extended lymph node dissection versus neoadjuvant therapy with limited lymph node dissection on biochemical recurrence in high-risk prostate cancer patients treated with radical prostatectomy: a multi-institutional analysis. Med Oncol. 2017 Jan;34(1):1. Epub 2016 Nov 26. PubMed PMID: 27889880.

16: Flaig TW, Potluri RC, Ng Y, Todd MB, Mehra M, Higano CS. Disease and Treatment Characteristics of Men Diagnosed With Metastatic Hormone-Sensitive Prostate Cancer in Real Life: Analysis From a Commercial Claims Database. Clin Genitourin Cancer. 2017 Apr;15(2):273-279.e1. doi: 10.1016/j.clgc.2016.10.002. Epub 2016 Oct 18. PubMed PMID: 27876504.

17: Reichert ZR, Hussain M. Androgen Receptor and Beyond, Targeting Androgen Signaling in Castration-Resistant Prostate Cancer. Cancer J. 2016 Sep/Oct;22(5):326-329. Review. PubMed PMID: 27749325.

18: Qin Z, Li X, Zhang J, Tang J, Han P, Xu Z, Yu Y, Yang C, Wang C, Xu T, Xu Z, Zou Q. Chemotherapy with or without estramustine for treatment of castration-resistant prostate cancer: A systematic review and meta-analysis. Medicine (Baltimore). 2016 Sep;95(39):e4801. doi: 10.1097/MD.0000000000004801. Review. PubMed PMID: 27684806; PubMed Central PMCID: PMC5265899.

19: Murachi K, Kumagai T, Masuda T, Nakanishi T, Tanaka S, Tajima K, Takebe Y, Oda T. [Efficacy and Prognostic Factors of Estracyt ® in Patients with Castration-Resistant Prostate Cancer (CRPC) : From the Data Analysis of Estracyt ® Special Drug Use Investigation]. Hinyokika Kiyo. 2016 Jun;62(6):295-306. Japanese. PubMed PMID: 27452492.

20: Collado-Borrell R, Escudero-Vilaplana V, Romero-Jiménez R, Iglesias-Peinado I, Herranz-Alonso A, Sanjurjo-Sáez M. Oral antineoplastic agent interactions with medicinal plants and food: an issue to take into account. J Cancer Res Clin Oncol. 2016 Nov;142(11):2319-30. doi: 10.1007/s00432-016-2190-8. Epub 2016 Jun 17. Review. PubMed PMID: 27316629.