CHEBI:4868 - estramustine

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ChEBI Name estramustine
ChEBI ID CHEBI:4868
Definition A carbamate ester obtained by the formal condensation of the hydroxy group of 17β-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H31Cl2NO3
Net Charge 0
Average Mass 440.40300
Monoisotopic Mass 439.16810
InChI InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
InChIKey FRPJXPJMRWBBIH-RBRWEJTLSA-N
SMILES [H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc1cc(OC(=O)N(CCCl)CCCl)ccc21
Roles Classification
Biological Role(s): alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
radiation protective agent

View more via ChEBI Ontology
ChEBI Ontology
Outgoing estramustine (CHEBI:4868) has functional parent 17β-estradiol (CHEBI:16469)
estramustine (CHEBI:4868) has role alkylating agent (CHEBI:22333)
estramustine (CHEBI:4868) has role antineoplastic agent (CHEBI:35610)
estramustine (CHEBI:4868) has role radiation protective agent (CHEBI:66987)
estramustine (CHEBI:4868) is a 17β-hydroxy steroid (CHEBI:35343)
estramustine (CHEBI:4868) is a carbamate ester (CHEBI:23003)
estramustine (CHEBI:4868) is a organochlorine compound (CHEBI:36683)
Incoming estramustine phosphate (CHEBI:68643) has functional parent estramustine (CHEBI:4868)
IUPAC Name
(17β)-17-hydroxyestra-1(10),2,4-trien-3-yl bis(2-chloroethyl)carbamate
INNs Sources
estramustina ChEBI
estramustine ChEBI
estramustinum ChEBI
Synonyms Sources
17β-Estradiol 3-(bis(2-chloroethyl)carbamate) ChemIDplus
Estradiol 3-(N,N-bis(2-chloroethyl)carbamate) ChemIDplus
Estramustine KEGG COMPOUND
Manual Xrefs Databases
1065 DrugCentral
BE646319 Patent
C11228 KEGG COMPOUND
D04066 KEGG DRUG
DB01196 DrugBank
Estramustine Wikipedia
HMDB0015327 HMDB
LMST02010038 LIPID MAPS
US3299104 Patent
View more database links
Registry Numbers Types Sources
2998-57-4 CAS Registry Number ChemIDplus
5637599 Reaxys Registry Number Reaxys
5637599 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11131983 PubMed citation Europe PMC
15762353 PubMed citation Europe PMC
7638085 PubMed citation Europe PMC
Last Modified
22 February 2017