# Alestramustine
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Alestramustine
> Markdown URL: https://mediated.wiki/source/Alestramustine.md
> Source: https://en.wikipedia.org/wiki/Alestramustine
> Source revision: 1329020122
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-3-[''bis''(2-Chloroethyl)carbamoyloxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] (2''S'')-2-aminopropanoate
| image = Alestramustine.svg
| image_class = skin-invert-image
| width = 250px
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| pregnancy_AU =
| pregnancy_US =
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| routes_of_administration =
| class = [Chemotherapeutic agent](/source/Chemotherapeutic_agent); [Estrogen](/source/Estrogen_(medication)); [Estrogen ester](/source/Estrogen_ester)
| bioavailability =
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| CAS_number_Ref =
| CAS_number = 139402-18-9
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| PubChem = 20055302
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| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 16736564
| UNII = 81U8A51CHK
| ChEMBL = 2106670
| synonyms = Alanylestramustine; Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(L-alaninate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(2β-aminopropanoate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-((2''S'')-2-aminopropanoate)
| C=26 | H=36 | Cl=2 | N=2 | O=4
| SMILES = CC(C(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl)C)N
| StdInChI_Ref =
| StdInChI = 1S/C26H36Cl2N2O4/c1-16(29)24(31)34-23-8-7-22-21-5-3-17-15-18(33-25(32)30(13-11-27)14-12-28)4-6-19(17)20(21)9-10-26(22,23)2/h4,6,15-16,20-23H,3,5,7-14,29H2,1-2H3/t16-,20+,21+,22-,23-,26-/m0/s1
| StdInChIKey_Ref =
| StdInChIKey = NRUFLTXGIPFVSH-KBVRNWHJSA-N
}}
'''Alestramustine''' ({{abbrlink|INN|International Nonproprietary Name}}), also known as '''estradiol 3-(''bis''(2-chloroethyl)carbamate) 17β-(L-alaninate)''', is a [cytostatic](/source/cytostatic) [antineoplastic agent](/source/antineoplastic_agent) which was never marketed.[{{cite web | title = Alestramustine | author = NCI Thesaurus | url = https://evsexplore.semantics.cancer.gov/evsexplore/concept/ncit/C77370 | access-date = 24 June 2016}}][{{cite book| vauthors = Milne GW |title=Ashgate Handbook of Antineoplastic Agents|url=https://books.google.com/books?id=ZNkhAQAAMAAJ|date=1 July 2000|publisher=Wiley|isbn=978-0-566-08382-2|page=5}}] It is the [L-alanine](/source/alanine) [ester](/source/ester) of [estramustine](/source/estramustine), which is a combination of the [nitrogen mustard](/source/nitrogen_mustard) [normustine](/source/normustine) coupled via a [carbamate](/source/carbamate) to the [estrogen](/source/estrogen_(medication)) [estradiol](/source/estradiol_(medication)).[{{cite book| vauthors = Tripathi KD |title=Essentials of Medical Pharmacology|url=https://books.google.com/books?id=FfG8AQAAQBAJ&pg=PA866|date=30 September 2013|publisher=JP Medical Ltd|isbn=978-93-5025-937-5|pages=866–}}] Alestramustine acts as a [prodrug](/source/prodrug) to estramustine, and also forms estradiol as a [byproduct](/source/by-product).