Estramustine phosphate sodium
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MedKoo CAT#: 100310

CAS#: 52205-73-9 (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).


Price and Availability

Size Price Shipping out time Quantity
100mg USD 160 Same day
500mg USD 700 Same day
1g USD 1050 Same day
2g USD 1850 Same day
5g USD 3150 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-23. Prices are subject to change without notice.

Estramustine phosphate sodium, purity > 97%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100310
Name: Estramustine phosphate sodium
CAS#: 52205-73-9 (sodium)
Chemical Formula: C23H30Cl2NNa2O6P
Exact Mass:
Molecular Weight: 564.35
Elemental Analysis: C, 48.95; H, 5.36; Cl, 12.56; N, 2.48; Na, 8.15; O, 17.01; P, 5.49


Related CAS #: 52205-73-9 (sodium)   1227300-83-5 (sodium hydrate)   4891-15-0 (free acid)   2998-57-4  

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+]


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

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


References

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.