XIV

Source 📝

Chemical compound
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
  • ※-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta※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
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. 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.

See also

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.



Stub icon

This antineoplastic/immunomodulatory drug article is a stub. You can help XIV by, expanding it.

Stub icon

This drug article relating to the genito-urinary system is a stub. You can help XIV by expanding it.

Stub icon

This article about a steroid is a stub. You can help XIV by expanding it.

Text is available under the "Creative Commons Attribution-ShareAlike License." Additional terms may apply.