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User:Mr. Ibrahem/Estramustine phosphate

< User:Mr. Ibrahem
Mr. Ibrahem/Estramustine phosphate
Clinical data
Trade namesEmcyt, Estracyt, others
Other namesEstradiol normustine phosphate; EMP; Leo 299; NSC-89199; Ro 21-8837/001; Estradiol 3-normustine 17β-phosphate; Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(dihydrogen phosphate)
AHFS/Drugs.comMonograph
MedlinePlusa608046
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
Drug classChemotherapeutic agent (alkylating agent)[1]
Legal status
Legal status
Pharmacokinetic data
Bioavailability44–75% (as estramustine and estromustine)[2]
Protein binding• Estradiol: 98%[3]
• Estrone: 96%[3]
MetabolismLiver, intestines[4][2][7]
Metabolites• Estramustine[4][2]
• Estromustine[4][2]
• Estradiol[4][2]
• Estrone[4][2]
• Phosphoric acid[4][2]
• Normustine[5]
Elimination half-life• EMP: 1.27 hours[6]
• Estromustine: 10–14 hrs[2]
• Estrone: 15–17 hours[2]
ExcretionBile, feces (2.9–4.8%)[2][7]
Identifiers
  • [(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
Chemical and physical data
FormulaC23H32Cl2NO6P
Molar mass520.38 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OP(=O)(O)O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
  • 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
  • Key:ADFOJJHRTBFFOF-RBRWEJTLSA-N

Estramustine phosphate (EMP), sold under the brand names Emcyt among others, is a medication used to treat prostate cancer.[8] Specifically it is used when the disease is hormone refractory.[8] It is taken by mouth three to four times per day.[8]

Common side effects include diarrhea, heart failure, low red blood cells, breast enlargement, liver problems, blood clots, and nausea.[9] Other side effects may include sexual dysfunction, high blood pressure, and angioedema.[8] Use in pregnancy may harm the baby.[8] It is made by joining an estradiol with a nitrogen mustard.[10]

Estramustine phosphate was introduced for medical use in the early 1970s.[4] It is available in the United States, Canada, the United Kingdom, and other European countries, among others.[1] In the United Kingdom 100 tablets of 140 mg costs the NHS about £170 as of 2021.[9] This amount in the United States costs about 1,600 USD.[11]

References edit

  1. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 406–407. ISBN 978-3-88763-075-1. Archived from the original on 2021-06-07. Retrieved 2021-08-24.
  2. ^ a b c d e f g h i j Bergenheim AT, Henriksson R (February 1998). "Pharmacokinetics and pharmacodynamics of estramustine phosphate". Clin Pharmacokinet. 34 (2): 163–72. doi:10.2165/00003088-199834020-00004. PMID 9515186. S2CID 1943973.
  3. ^ a b Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324. Archived (PDF) from the original on 2016-08-22. Retrieved 2021-08-24.
  4. ^ a b c d e f g Kitamura T (February 2001). "Necessity of re-evaluation of estramustine phosphate sodium (EMP) as a treatment option for first-line monotherapy in advanced prostate cancer". Int. J. Urol. 8 (2): 33–6. doi:10.1046/j.1442-2042.2001.00254.x. PMID 11240822. S2CID 43384150.
  5. ^ Inoue, Takahiro (2018). "Role of Estramustine Phosphate and Other Estrogens for Castration-Resistant Prostate Cancer". Hormone Therapy and Castration Resistance of Prostate Cancer. pp. 249–256. doi:10.1007/978-981-10-7013-6_26. ISBN 978-981-10-7012-9.
  6. ^ Perry CM, McTavish D (July 1995). "Estramustine phosphate sodium. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in prostate cancer". Drugs Aging. 7 (1): 49–74. doi:10.2165/00002512-199507010-00006. PMID 7579781. S2CID 36725810.
  7. ^ a b "Emcyt (estramustine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 21 February 2014. Retrieved 8 February 2014.
  8. ^ a b c d e f "Estramustine Monograph for Professionals". Drugs.com. Archived from the original on 7 January 2022. Retrieved 16 December 2021.
  9. ^ a b c BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 940. ISBN 978-0857114105.
  10. ^ "Drug Information Portal - U.S. National Library of Medicine - Quick Access to Quality Drug Information". druginfo.nlm.nih.gov. Archived from the original on 11 January 2022. Retrieved 16 December 2021.
  11. ^ "Estramustine Phosphate Sodium Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 16 December 2021.
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