Structure via PubChem · Public domain (PubChem)
estramustine
Sign in to saveAlso known as 17β-estradiol 3-(bis(2-chloroethyl)carbamate), estradiol 3-(N,N-bis(2-chloroethyl)carbamate), 17beta-estradiol 3-(bis(2-chloroethyl)carbamate)
Estramustine (, , ) is an estrogen and cytostatic antineoplastic agent which was never marketed. It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body. Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer. ==Synthesis== Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine is treated with phosgene to give the acid chloride of normustine. This reacts with the phenolic hydroxyl group of e
Chemical data
- Formula
- C23H31Cl2NO3
- Molecular weight
- 440.4 g/mol
- IUPAC name
- [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
- InChIKey
- FRPJXPJMRWBBIH-RBRWEJTLSA-N
- XLogP
- 4
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- neoplasm, metastatic prostate cancer, prostate adenocarcinoma, breast cancer
via ChEMBL · EBI
Research
1,285 papersvia PubMed
Wikidata facts
- Subclass of
- 17α/β-estradiol
- Mass
- 439.168099
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₃H₃₁Cl₂NO₃
- medical condition treated
- prostate cancer
- canonical SMILES
- CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
- Commons category
- Estramustine
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Estramustine (, , ) is an estrogen and cytostatic antineoplastic agent which was never marketed. It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body. Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer. ==Synthesis== Estramustine is a carbamate derivative of the natural hormone, estradiol. The amine is treated with phosgene to give the acid chloride of normustine. This reacts with the phenolic hydroxyl group of estradiol in the presence of a base to give estramustine.
== See also == Estradiol mustard List of hormonal cytostatic antineoplastic agents List of estrogen esters § Estradiol esters
Excerpted from Wikipedia’s “estramustine” article, available under the CC BY-SA 4.0 licence.