alestramustine

{{Short description|Chemical compound}}

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| IUPAC_name = [(8R,9S,13S,14S,17S)-3-[bis(2-Chloroethyl)carbamoyloxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] (2S)-2-aminopropanoate

| image = Alestramustine.svg

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| class = Chemotherapeutic agent; Estrogen; Estrogen ester

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| CAS_number = 139402-18-9

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| PubChem = 20055302

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| 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-((2S)-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

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| StdInChIKey = NRUFLTXGIPFVSH-KBVRNWHJSA-N

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Alestramustine ({{abbrlink|INN|International Nonproprietary Name}}), also known as estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed.{{cite web | title = Alestramustine | author = NCI Thesaurus | url = https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=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 ester of estramustine, which is a combination of the nitrogen mustard normustine coupled via a carbamate to the estrogen estradiol.{{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 to estramustine, and also forms estradiol as a byproduct. The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division. Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.