Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0645)
Drug Name
Estramustine
Synonyms
Estracyt; Estramustina; Estramustina [INN-Spanish]; Estramustinum; Estramustinum [INN-Latin]; estramustine; 17beta-Estradiol 3-(bis(2-chloroethyl)carbamate); 2998-57-4; 35LT29625A; C23H31Cl2NO3; CHEBI:4868; CHEMBL1575; DSSTox_CID_26458; DSSTox_GSID_46458; DSSTox_RID_81632; Emcyt; Estradiol 3-(N,N-bis(2-chloroethyl)carbamate); NCGC00164581-01; UNII-35LT29625A; [(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
Indication Prostate cancer [ICD11: 2C82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 440.4 Topological Polar Surface Area 49.8
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
259331
PubChem SID
13407 ; 396503 ; 7978494 ; 9402932 ; 11446334 ; 16850624 ; 24702260 ; 26758003 ; 41280965 ; 46508765 ; 47206023 ; 56352913 ; 57400709 ; 76429291 ; 93166640 ; 103589705 ; 104467345 ; 119525106 ; 125083748 ; 126616924 ; 127301152 ; 127301153 ; 127301154 ; 127301155 ; 127301156 ; 127301157 ; 127301158 ; 127301159 ; 127301160 ; 127301161 ; 127301162 ; 127301163 ; 127301164 ; 127301165 ; 127889566 ; 134983568 ; 136342495 ; 137129046 ; 140230311 ; 144205760 ; 162174802 ; 162221629 ; 163134406 ; 163883659 ; 164788803 ; 170466403 ; 175266702 ; 175612197 ; 179150282 ; 184545983
ChEBI ID
ChEBI:4868
CAS Number
2998-57-4
TTD Drug ID
D03SRY
Formula
C23H31Cl2NO3
Canonical SMILES
CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Estradiol-17 beta DM000867
5757
Unclear 1 [3] , [4]
Estromustine DM000885
124946
Unclear 1 [3] , [4]
Estrone DM003062
5870
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000958 Estramustine Estradiol Unclear Unclear [3], [4]
MR000959 Estramustine Estromustine Unclear Unclear [3], [4]
MR000957 Estromustine Estrone Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Estramustine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Activity of docetaxel with or without estramustine phosphate versus mitoxantrone in androgen dependent and independent human prostate cancer xenografts. J Urol. 2003 May;169(5):1729-34.
3 Simultaneous determination of estramustine phosphate and its four metabolites in human plasma by liquid chromatography-ionspray mass spectrometry Biomed Chromatogr. 2004 Jun;18(5):293-301. doi: 10.1002/bmc.319.
4 Differential uptake of estramustine phosphate metabolites and its correlation with the levels of estramustine binding protein in prostate tumor tissue Clin Cancer Res. 1998 Sep;4(9):2079-84.

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