Natural Product (NP) Details

General Information of the NP (ID: NP1427)
Name
Estramustine
Synonyms
estramustine; 2998-57-4; Estramustina; Estramustinum; Emcyt; Estramustinum [INN-Latin]; Estramustina [INN-Spanish]; UNII-35LT29625A; Estradiol 3-(N,N-bis(2-chloroethyl)carbamate); 17beta-Estradiol 3-(bis(2-chloroethyl)carbamate); CHEMBL1575; Estradiol 3-[bis(2-chloroethyl)carbamate]; CHEBI:4868; NSC-89201; 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; LEO 275; NCGC00164581-01; Estradiol 3-(bis(2-chloroethyl)carbamate); Estradiol, 3-[bis(2-chloroethyl)carbamate]; Ro 22-2296/000; DSSTox_CID_26458; DSSTox_RID_81632; DSSTox_GSID_46458; (8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl bis(2-chloroethyl)carbamate; RO 21-8837; NSC 89201; estra-1,3,5(10)-triene-3,17beta-diol, 3-[bis(2-chloroethyl)carbamate]; C23H31Cl2NO3; CAS-2998-57-4; Estradiol, 3-(bis(2-chloroethyl)carbamate); Estradiol 3-[N,N-Bis(2-chloroethyl)carbamate]; MLS002701936; 17.beta.-Estradiol 3-[bis(2-chloroethyl)carbamate]; Estramustine (USAN/INN); estramustin; NSC89201; Estramustine [USAN:INN:BAN]; EINECS 221-076-3; SCHEMBL4252; Estramustin Sodium Phosphate; BIDD:GT0482; GTPL9076; DTXSID8046458; HMS3715D22; ZINC4099032; Tox21_112207; BDBM50333646; LMST02010038; (17beta)-17-hydroxyestra-1(10),2,4-trien-3-yl bis(2-chloroethyl)carbamate; AKOS025402444; Tox21_112207_1; AC-9163; CCG-221220; DB01196; NCGC00164581-02; AS-12259; NCI60_041982; Ro-222296000; Ro-22-2296000; Ro-22-2296-000; C11228; D04066; 15163-EP2272827A1; 15163-EP2275420A1; 15163-EP2295055A2; 15163-EP2295416A2; 15163-EP2298748A2; 15163-EP2298764A1; 15163-EP2298765A1; 15163-EP2305642A2; 15163-EP2308833A2; 15163-EP2308861A1; 15163-EP2311453A1; 15163-EP2311840A1; 15163-EP2316832A1; 15163-EP2316833A1; 998E574; Q412939; W-106963; Carbamic acid, bis(2-chloroethyl)-, 17beta-hydroxyestra-1,3,5(10)-trien-3-yl ester; Estra-1,3,5(10)-triene-3,17-diol (17beta)-, 3-(bis(2-chloroethyl)carbamate) (9CI); Estra-1,3,5(10)-triene-3,17-diol, 3-(bis(2-chloroethyl)carbamate), (17beta)-; Estra-1,5(10)-triene-3,17-diol (17.beta.)-, 3-[bis(2-chloroethyl)carbamate]; Estra-1,5(10)-triene-3,17-diol, 3-[bis(2-chloroethyl)carbamate], (17.beta.)-; Bis-(2-chloro-ethyl)-carbamic acid 17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Prostate cancer [ICD-11: 2C82] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.774
 
MDCK Permeability
 -4.588
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.075
 
PPB
 85.8%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 ++
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 ++
CYP3A4 inhibitor
 -
CYP3A4 substrate
 -
CYP2B6 inhibitor
 - -
CYP2B6 substrate
 +++
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 5.966
 
T1/2
 0.852
Toxicity
DILI
 -
 
Rat Oral Acute Toxicity
 +++
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 ++
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 +++
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C23H31Cl2NO3
PubChem CID
259331
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
CAS Number
CAS 2998-57-4
ChEBI ID
CHEBI:4868
TTD Drug ID
D03SRY
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Docetaxel      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 These results provide novel molecular targets of docetaxel and estramustine combination treatment in prostate cancer cells.
Target and Pathway
Target(s) Estramustine binding protein (EMBP)  Molecule Info  [3]
References
Reference 1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
Reference 2 Gene expression profiling revealed novel molecular targets of docetaxel and estramustine combination treatment in prostate cancer cells. Mol Cancer Ther. 2005 Mar;4(3):389-98.
Reference 3 Estramustine binding protein in primary tumours and metastases of malignant melanoma. Melanoma Res. 1994 Dec;4(6):401-5.
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