{{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
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Chemotherapeutic agent; Estrogen; Estrogen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = | CAS_number = 139402-18-9 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 20055302 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 16736564 | UNII = 81U8A51CHK | ChEMBL = 2106670 | synonyms = Alanylestramustine; Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(<small>L</small>-alaninate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(2β-aminopropanoate); Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-((2''S'')-2-aminopropanoate)
<!--Chemical data--> | 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-(<small>L</small>-alaninate)''', is a cytostatic antineoplastic agent which was never marketed.<ref name="NCI">{{cite web | title = Alestramustine | author = NCI Thesaurus | url = https://evsexplore.semantics.cancer.gov/evsexplore/concept/ncit/C77370 | access-date = 24 June 2016}}</ref><ref name="Milne2000">{{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}}</ref> It is the <small>L</small>-alanine ester of estramustine, which is a combination of the nitrogen mustard normustine coupled via a carbamate to the estrogen estradiol.<ref name="NCI" /><ref name="Tripathi2013">{{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–}}</ref> Alestramustine acts as a prodrug to estramustine, and also forms estradiol as a byproduct.<ref name="NCI" /><ref name="Tripathi2013" /> The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division.<ref name="NCI" /><ref name="Tripathi2013" /> Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.<ref name="NCI" />
==See also== * List of hormonal cytostatic antineoplastic agents * List of estrogen esters § Estradiol esters
==References== {{Reflist}}
{{Estrogen receptor modulators}}
Category:Abandoned drugs Category:Antineoplastic drugs Category:Chloroethyl compounds Category:Estradiol esters Category:Estranes Category:Hormonal antineoplastic drugs Category:Nitrogen mustards Category:Prodrugs Category:Synthetic estrogens
{{Antineoplastic-drug-stub}} {{Genito-urinary-drug-stub}} {{Estrane-stub}}