estramustine   Click here for help

GtoPdb Ligand ID: 9076

Synonyms: Emcyt® | Estracyt®
Approved drug
estramustine is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: Estramustine is a synthetic analogue combining estradiol and nornitrogen mustard. It is a DNA alkylating agent with antineoplastic activity.
Marketed formulations contain estramustine phosphate sodium (PubChem CID 444000).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: estramustine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 49.77
Molecular weight 439.17
XLogP 5.74
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES ClCCN(C(=O)Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C)CCCl
Isomeric SMILES ClCCN(C(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)CCCl
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
No information available.
Summary of Clinical Use Click here for help
Estramustine is approved to treat metastatic or progressive prostate cancer.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Estramustine alkylates and cross-links DNA, resulting in disruption of DNA function, cell cycle arrest, and apoptosis.
External links Click here for help