Introduction：Basic information about CAS 4891-15-0|Estramustine phosphate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Estramustine phosphate |
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| CAS Number | 4891-15-0 | Molecular Weight | 520.38300 |
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| Density | 1.4g/cm3 | Boiling Point | 661.2ºC at 760mmHg |
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| Molecular Formula | C23H32Cl2NO6P | Melting Point | / |
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| MSDS | / | Flash Point | 353.7ºC |
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Names
| Name | estramustine phosphate |
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| Synonym | More Synonyms |
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Estramustine phosphate BiologicalActivity
| Description | Estramustine phosphate, an estradiol analog, is an orally active antimicrotubule chemotherapy agent. Estramustine phosphate depolymerises microtubules by binding to microtubule associated proteins (MAPs) and/or to tubulin. Estramustine phosphate can interfere mitosis, trigger cell death and induce apoptosis, which can be used for the research of cancer like prostate cancer[1][2][3]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>EndocrinologySignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Cytoskeleton >>Microtubule/Tubulin |
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| In Vitro | Estramustine phosphate (1 µg/mL, 48 h) suppresses PC3 cell growth[1]. Estramustine phosphate (2 µg/mL, 48 h) elevates phosphatidylserine eversion amount on PC3 cells and induces PC3 cell apoptosis through reducing miR-31[1]. Estramustine phosphate (0-40 µM, 24-72 h) inhibits cell proliferation and tubulin cytoskeleton in RAW 264.7 cells[2]. Estramustine phosphate (10 µM, 24 h) inhibits TGF-β-induced RAW 264.7 cell migration, as well as TGF-β-induced uPA production by inhibiting Smad3 activation[2]. Cell Viability Assay[1] Cell Line: PC3 cells Concentration: 1 µg/ mL Incubation Time: 48 h Result: Suppressed PC3 cell growth. Immunofluorescence[2] Cell Line: RAW 264.7 cells Concentration: 10 µM Incubation Time: 24 h Result: Disrupted the interphase microtubules. Cell Migration Assay [2] Cell Line: 18 h of TGF-β treated RAW 264.7 cells Concentration: 10 µM Incubation Time: 24 h Result: Inhibited TGF-β-Induced Cell Migration. |
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| In Vivo | Estramustine phosphate (Intraperitoneal injection, 4 or 12 mg/kg, a daily dose for 2 weeks) inhibits PAC120 tumor growth 53% by day 35[3]. Animal Model: Human prostate cancer xenograft PAC120[3] Dosage: 4 or 12 mg/kg, a daily dose for 2 weeks. Administration: Intraperitoneal injection Result: Inhibited PAC120 tumor growth 53% by day 35. |
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| References | [1]. C Wei, et al. 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. [2]. Sonja S Mojsilovic, et al. Estramustine Phosphate Inhibits TGF- β-Induced Mouse Macrophage Migration and Urokinase-Type Plasminogen Activator Production. Anal Cell Pathol (Amst). 2018 Sep 2;2018:3134102. [3]. Stephane Oudard, et al. Activity of docetaxel with or without estramustine phosphate versus mitoxantrone in androgen dependent and independent human prostate cancer xenografts. J Urol. 2003 May;169(5):1729-34. |
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Chemical & Physical Properties
| Density | 1.4g/cm3 |
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| Boiling Point | 661.2ºC at 760mmHg |
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| Molecular Formula | C23H32Cl2NO6P |
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| Molecular Weight | 520.38300 |
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| Flash Point | 353.7ºC |
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| Exact Mass | 519.13400 |
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| PSA | 106.11000 |
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| LogP | 5.29900 |
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| Index of Refraction | 1.594 |
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| InChIKey | ADFOJJHRTBFFOF-RBRWEJTLSA-N |
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| SMILES | CC12CCC3c4ccc(OC(=O)N(CCCl)CCCl)cc4CCC3C1CCC2OP(=O)(O)O |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- KG4300000
- CHEMICAL NAME :
- Estradiol, 3-(bis(2-chloroethyl)carbamate) dihydrogen phosphate
- CAS REGISTRY NUMBER :
- 4891-15-0
- LAST UPDATED :
- 199707
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C23-H32-Cl2-N-O6-P
- MOLECULAR WEIGHT :
- 520.43
- WISWESSER LINE NOTATION :
- L E5 B666TTT&J E1 FOPQQO OOVN2G2G
HEALTH HAZARD DATAACUTE TOXICITY DATAMUTATION DATA - TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Bacteria - Salmonella typhimurium
- DOSE/DURATION :
- 1000 ug/plate
- REFERENCE :
- URLRA5 Urological Research. (Springer Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1973- Volume(issue)/page/year: 7,119,1979
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Synonyms
| LS 299 |
| [(8R,9S,13S,14S,17S)-13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate |
| ESTRAMUSTINE PHOSPHATE |
| Leo 299 |
| Emcyt (free acid) |
| (17|A)-17-(phosphonooxy)estra-1,3,5(10)-trien-3-yl bis(2-chloroethyl)carbamate |
| Estradiol,3-(bis(2-chloroethyl)carbamate) dihydrogen phosphate |
