MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 598576 | Name: Estramustine
Featured

Description:

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

Estramustine is a nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.

Chemical Structure

Estramustine
Estramustine
CAS#2998-57-4 (free base)

Theoretical Analysis

MedKoo Cat#: 598576

Name: Estramustine

CAS#: 2998-57-4 (free base)

Chemical Formula: C23H31Cl2NO3

Exact Mass: 439.1681

Molecular Weight: 440.40

Elemental Analysis: C, 62.73; H, 7.10; Cl, 16.10; N, 3.18; O, 10.90

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
100mg USD 850.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
2998-57-4 (free base) 4891-15-0 (phosphate) 52205-73-9 (phosphate sodium)
Synonym
Estramustine; NSC 89201; NSC-89201; NSC89201; LEO 275; LEO-275; LEO275; RO 21-8837;
IUPAC/Chemical Name
(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl bis(2-chloroethyl)carbamate
InChi Key
FRPJXPJMRWBBIH-RBRWEJTLSA-N
InChi Code
InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
SMILES Code
C[C@@]12[C@@H](O)CC[C@@]1([H])[C@]3([H])CCC4=C(C=CC(OC(N(CCCl)CCCl)=O)=C4)[C@@]3([H])CC2
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).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 440.40 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
1: Bissinger R, Modicano P, Frauenfeld L, Lang E, Jacobi J, Faggio C, Lang F. Estramustine-induced suicidal erythrocyte death. Cell Physiol Biochem. 2013;32(5):1426-36. PubMed PMID: 24296399. 2: Zhang C, Jing T, Wang F, Gao X, Xu C, Sun Y. Chemotherapy plus estramustine for management of castration-resistant prostate cancer: meta-analysis of randomized controlled trials. Actas Urol Esp. 2014 Apr;38(3):184-91. doi: 10.1016/j.acuro.2013.07.010. Epub 2014 Feb 5. English, Spanish. PubMed PMID: 24507454. 3: Nakai Y, Nishimura K, Nakayama M, Uemura M, Takayama H, Nonomura N, Tsujimura A; Osaka CRPC Clinical Study Collaboration. Weekly, low-dose docetaxel combined with estramustine for Japanese castration-resistant prostate cancer: its efficacy and safety profile compared with tri-weekly standard-dose treatment. Int J Clin Oncol. 2014 Feb;19(1):165-72. doi: 10.1007/s10147-013-0536-7. Epub 2013 Mar 1. PubMed PMID: 23456140. 4: 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. 5: Petrioli R, Roviello G, Fiaschi AI, Laera L, Bianco V, Ponchietti R, Barbanti G, Francini E. Low-Dose Estramustine Phosphate and Concomitant Low-Dose Acetylsalicylic Acid in Heavily Pretreated Patients With Advanced Castration-Resistant Prostate Cancer. Clin Genitourin Cancer. 2015 Oct;13(5):441-6. doi: 10.1016/j.clgc.2015.03.004. Epub 2015 Mar 26. PubMed PMID: 25920994. 6: Kuramoto T, Inagaki T, Fujii R, Sasaki Y, Nishizawa S, Nanpo Y, Matusmura N, Kohjimoto Y, Hara I. Docetaxel in combination with estramustine and prednisolone for castration-resistant prostate cancer. Int J Clin Oncol. 2013 Oct;18(5):890-7. doi: 10.1007/s10147-012-0463-z. Epub 2012 Aug 31. PubMed PMID: 22936562. 7: Petrylak DP, Tangen CM, Hussain MH, Lara PN Jr, Jones JA, Taplin ME, Burch PA, Berry D, Moinpour C, Kohli M, Benson MC, Small EJ, Raghavan D, Crawford ED. Docetaxel and estramustine compared with mitoxantrone and prednisone for advanced refractory prostate cancer. N Engl J Med. 2004 Oct 7;351(15):1513-20. PubMed PMID: 15470214. 8: Hatano K, Nishimura K, Nakai Y, Yoshida T, Sato M, Kawashima A, Mukai M, Nagahara A, Uemura M, Oka D, Nakayama M, Takayama H, Shimizu K, Meguro N, Tanigawa T, Yamaguchi S, Tsujimura A, Nonomura N. Weekly low-dose docetaxel combined with estramustine and dexamethasone for Japanese patients with metastatic castration-resistant prostate cancer. Int J Clin Oncol. 2013 Aug;18(4):704-10. doi: 10.1007/s10147-012-0429-1. Epub 2012 Jun 12. PubMed PMID: 22688162. 9: Matsumoto K, Tanaka N, Hayakawa N, Ezaki T, Suzuki K, Maeda T, Ninomiya A, Nakamura S. Efficacy of estramustine phosphate sodium hydrate (EMP) monotherapy in castration-resistant prostate cancer patients: report of 102 cases and review of literature. Med Oncol. 2013 Dec;30(4):717. doi: 10.1007/s12032-013-0717-2. Epub 2013 Sep 5. PubMed PMID: 24005812. 10: Ravery V, Fizazi K, Oudard S, Drouet L, Eymard JC, Culine S, Gravis G, Hennequin C, Zerbib M. The use of estramustine phosphate in the modern management of advanced prostate cancer. BJU Int. 2011 Dec;108(11):1782-6. doi: 10.1111/j.1464-410X.2011.10201.x. Epub 2011 Jul 14. Review. PubMed PMID: 21756277. 11: Sk UH, Dixit D, Sen E. Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation. Eur J Med Chem. 2013 Oct;68:47-57. doi: 10.1016/j.ejmech.2013.07.007. Epub 2013 Jul 27. PubMed PMID: 23954240. 12: Fizazi K, Lesaunier F, Delva R, Gravis G, Rolland F, Priou F, Ferrero JM, Houedé N, Mourey L, Theodore C, Krakowski I, Berdah JF, Baciuchka M, Laguerre B, Fléchon A, Ravaud A, Cojean-Zelek I, Oudard S, Labourey JL, Lagrange JL, Chinet-Charrot P, Linassier C, Deplanque G, Beuzeboc P, Geneve J, Davin JL, Tournay E, Culine S. A phase III trial of docetaxel-estramustine in high-risk localised prostate cancer: a planned analysis of response, toxicity and quality of life in the GETUG 12 trial. Eur J Cancer. 2012 Jan;48(2):209-17. doi: 10.1016/j.ejca.2011.10.015. Epub 2011 Nov 24. PubMed PMID: 22119204. 13: Minato A, Fujimoto N, Kubo T, Harada S, Akasaka S, Matsumoto T. Efficacy of estramustine phosphate according to risk classification of castration-resistant prostate cancer. Med Oncol. 2012 Dec;29(4):2895-900. doi: 10.1007/s12032-012-0178-z. Epub 2012 Feb 10. PubMed PMID: 22323054. 14: Qi WX, Shen Z, Yao Y. Docetaxel-based therapy with or without estramustine as first-line chemotherapy for castration-resistant prostate cancer: a meta-analysis of four randomized controlled trials. J Cancer Res Clin Oncol. 2011 Dec;137(12):1785-90. doi: 10.1007/s00432-011-1052-7. Epub 2011 Sep 14. PubMed PMID: 21915752. 15: Scott LM, Chen L, Daniel KG, Brooks WH, Guida WC, Lawrence HR, Sebti SM, Lawrence NJ, Wu J. Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs. Bioorg Med Chem Lett. 2011 Jan 15;21(2):730-3. doi: 10.1016/j.bmcl.2010.11.117. Epub 2010 Dec 4. PubMed PMID: 21193311; PubMed Central PMCID: PMC3034307. 16: Edgren M, Westlin JE, Letocha H, Nordgren H, Kälkner KM, Nilsson S. Estramustine-binding protein (EMBP) in renal cell carcinoma immunohistochemistry, immunoscintigraphy and in vitro estramustine effects. Acta Oncol. 1996;35(4):483-8. PubMed PMID: 8695166. 17: Kim WY, Whang YE, Pruthi RS, Baggstrom MQ, Rathmell WK, Rosenman JG, Wallen EM, Goyal LK, Grigson G, Watkins C, Godley PA. Neoadjuvant docetaxel/estramustine prior to radical prostatectomy or external beam radiotherapy in high risk localized prostate cancer: a phase II trial. Urol Oncol. 2011 Nov-Dec;29(6):608-13. doi: 10.1016/j.urolonc.2009.09.012. Epub 2009 Dec 21. PubMed PMID: 20022268. 18: Perry CM, McTavish D. Estramustine phosphate sodium. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in prostate cancer. Drugs Aging. 1995 Jul;7(1):49-74. Review. PubMed PMID: 7579781. 19: Swanson DA, Johnson DE. Estramustine phosphate (Emcyt) as treatment for metastatic renal carcinoma. Urology. 1981 Apr;17(4):344-6. PubMed PMID: 7013236. 20: Bergenheim AT, Henriksson R, Piepmeier JM, Yoshida D. Estramustine in malignant glioma. J Neurooncol. 1996 Oct;30(1):81-9. Review. PubMed PMID: 8865006.