MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 598577 | Name: Estramustine phosphate

Description:

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

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

Chemical Structure

Estramustine phosphate
Estramustine phosphate
CAS#4891-15-0 (phosphate)

Theoretical Analysis

MedKoo Cat#: 598577

Name: Estramustine phosphate

CAS#: 4891-15-0 (phosphate)

Chemical Formula: C23H32Cl2NO6P

Exact Mass: 0.0000

Molecular Weight: 520.38

Elemental Analysis: C, 53.09; H, 6.20; Cl, 13.62; N, 2.69; O, 18.45; P, 5.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
2998-57-4 (free base) 4891-15-0 (phosphate) 52205-73-9 (phosphate sodium)
Synonym
Estramustine phosphate; LS 299; LS-299; LS299; NSC 89199; NSC-89199; NSC89199; Estracyt;
IUPAC/Chemical Name
(8R,9S,13S,14S,17S)-13-methyl-17-(phosphonooxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl bis(2-chloroethyl)carbamate
InChi Key
ADFOJJHRTBFFOF-RBRWEJTLSA-N
InChi Code
InChI=1S/C23H32Cl2NO6P/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)/t18-,19-,20+,21+,23+/m1/s1
SMILES Code
C[C@@]12[C@@H](OP(O)(O)=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 520.38 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: 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. 2: Aurilio G, Graffeo R, Bagnardi V, Nolè F, Adamoli L, Pagani O, Gallerani E, Ferrari B, Pruneri G, Goldhirsch A. Estramustine phosphate sodium in heavily pretreated patients with metastatic breast cancer: a retrospective consecutive case series. Int J Clin Oncol. 2015 Feb;20(1):90-4. doi: 10.1007/s10147-014-0694-2. Epub 2014 Apr 12. PubMed PMID: 24722887. 3: 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. 4: Hayakawa N, Matsumoto K, Sato A, Sakamoto H, Ezaki T, Maeda T, Ninomiya A, Nakamura S. Efficacy of tegafur-uracil (UFT) administration in castration-resistant prostate cancer patients with a history of both alternative antiandrogen therapy and estramustine phosphate sodium hydrate therapy. Int Urol Nephrol. 2014 Jun;46(6):1123-9. doi: 10.1007/s11255-013-0634-5. Epub 2013 Dec 20. PubMed PMID: 24356920. 5: 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. 6: 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. 7: Koie T, Mitsuzuka K, Yoneyama T, Narita S, Kawamura S, Kaiho Y, Tsuchiya N, Tochigi T, Habuchi T, Arai Y, Ohyama C, Yoneyama T, Tobisawa Y. Neoadjuvant luteinizing-hormone-releasing hormone agonist plus low-dose estramustine phosphate improves prostate-specific antigen-free survival in high-risk prostate cancer patients: a propensity score-matched analysis. Int J Clin Oncol. 2015 Oct;20(5):1018-25. doi: 10.1007/s10147-015-0802-y. Epub 2015 Feb 15. PubMed PMID: 25681879. 8: 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. 9: 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. 10: 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. 11: 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. 12: Inoue T, Ogura K, Kawakita M, Tsukino H, Akamatsu S, Yamasaki T, Matsui Y, Segawa T, Sugino Y, Kamoto T, Kamba T, Tanaka S, Ogawa O. Effective and Safe Administration of Low-Dose Estramustine Phosphate for Castration-Resistant Prostate Cancer. Clin Genitourin Cancer. 2016 Feb;14(1):e9-e17. doi: 10.1016/j.clgc.2015.08.008. Epub 2015 Sep 2. PubMed PMID: 26433627. 13: Narita S, Tsuchiya N, Yuasa T, Maita S, Obara T, Numakura K, Tsuruta H, Saito M, Inoue T, Horikawa Y, Satoh S, Habuchi T. Outcome, clinical prognostic factors and genetic predictors of adverse reactions of intermittent combination chemotherapy with docetaxel, estramustine phosphate and carboplatin for castration-resistant prostate cancer. Int J Clin Oncol. 2012 Jun;17(3):204-11. doi: 10.1007/s10147-011-0275-6. Epub 2011 Jun 25. PubMed PMID: 21706123. 14: Narita S, Tsuchiya N, Kumazawa T, Maita S, Numakura K, Obara T, Tsuruta H, Saito M, Inoue T, Horikawa Y, Satoh S, Nanjyo H, Habuchi T. Short-term clinicopathological outcome of neoadjuvant chemohormonal therapy comprising complete androgen blockade, followed by treatment with docetaxel and estramustine phosphate before radical prostatectomy in Japanese patients with high-risk localized prostate cancer. World J Surg Oncol. 2012 Jan 4;10:1. doi: 10.1186/1477-7819-10-1. PubMed PMID: 22214417; PubMed Central PMCID: PMC3267659. 15: Bergenheim AT, Henriksson R. Pharmacokinetics and pharmacodynamics of estramustine phosphate. Clin Pharmacokinet. 1998 Feb;34(2):163-72. Review. PubMed PMID: 9515186. 16: Wang LG, Liu XM, Kreis W, Budman DR. Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor. Biochem Pharmacol. 1998 May 1;55(9):1427-33. PubMed PMID: 10076535. 17: Kylmälä T, Castrén-Kortekangas P, Seppänen J, Ylitalo P, Tammela TL. Effect of concomitant administration of clodronate and estramustine phosphate on their bioavailability in patients with metastasized prostate cancer. Pharmacol Toxicol. 1996 Sep;79(3):157-60. PubMed PMID: 8884875. 18: Gunnarsson PO, Forshell GP, Fritjofsson A, Norlén BJ. Plasma concentrations of estramustine phosphate and its major metabolites in patients with prostatic carcinoma treated with different doses of estramustine phosphate (Estracyt). Scand J Urol Nephrol. 1981;15(3):201-5. PubMed PMID: 7323739. 19: Soloway MS, deKernion JB, Gibbons RP, Johnson DE, Loening SA, Pontes JE, Prout GR Jr, Schmidt JD, Scott WW, Chu TM, Gaeta JF, Slack NH, Murphy GP. Comparison of estramustine phosphate and vincristine alone or in combination for patients with advanced, hormone refractory, previously irradiated carcinoma of the prostate. J Urol. 1981 May;125(5):664-7. PubMed PMID: 7230336. 20: Wallin M, Deinum J, Fridén B. Interaction of estramustine phosphate with microtubule-associated proteins. FEBS Lett. 1985 Jan 7;179(2):289-93. PubMed PMID: 2857133.