Article · Wikipedia archive · Last revised Jun 6, 2026

Alestramustine

Alestramustine, also known as estradiol 3-(bis carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed. 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. 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.

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Jun 6, 2026
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Alestramustine
Clinical data
Other namesAlanylestramustine; 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)
Drug classChemotherapeutic agent; Estrogen; Estrogen ester
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H36Cl2N2O4
Molar mass511.48 g·mol−1
3D model (JSmol)
  • CC(C(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl)C)N
  • InChI=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
  • Key:NRUFLTXGIPFVSH-KBVRNWHJSA-N

Alestramustine (INNTooltip International Nonproprietary Name), also known as estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed.12 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.13 Alestramustine acts as a prodrug to estramustine, and also forms estradiol as a byproduct.13 The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division.13 Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.1

See also

See also

References

References

  1. NCI Thesaurus. "Alestramustine". Retrieved 24 June 2016.
  2. Milne GW (1 July 2000). Ashgate Handbook of Antineoplastic Agents. Wiley. p. 5. ISBN 978-0-566-08382-2.
  3. Tripathi KD (30 September 2013). Essentials of Medical Pharmacology. JP Medical Ltd. pp. 866–. ISBN 978-93-5025-937-5.