ALESTRAMUSTINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H36Cl2N2O4
Molecular Weight	511.481
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](OC(=O)[C@H](C)N)[C@@]1(C)CC[C@]3([H])C4=CC=C(OC(=O)N(CCCl)CCCl)C=C4CC[C@@]23[H]

InChI

InChIKey=NRUFLTXGIPFVSH-KBVRNWHJSA-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

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Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C77370

Alestramustine is the l-alanine ester form of estramustine, a combination of the nitrogen mustard normustine coupled via a carbamate to estradiol, with antineoplastic activity. Upon conversion of alestramustine to estramustine, estramustine binds to microtubule-associated proteins (MAPs) and beta tubulin, thereby interfering with microtubule dynamics and leading to microtubule disassembly and cell cyle arrest. Due to the estrogen moiety, this agent is able to selectively bind to and be taken up by estrogen receptor-positive cells.

Approval Year

Patents

Name

Type

Language

ALESTRAMUSTINE

Official Name

English

ESTRADIOL 3-(BIS(2-CHLOROETHYL)CARBAMATE), 17-ESTER WITH L-ALANINE

Common Name

English

alestramustine [INN]

Common Name

English

L-ALANINE, (17.BETA.)-3-(((BIS(2-CHLOROETHYL)AMINO)CARBONYL)OXY)ESTRA-1,3,5(10)-TRIEN-17-YL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697