Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00247)
Name
Estramustine
Synonyms    Click to Show/Hide the Synonyms of This API
estramustine; 2998-57-4; Estramustina; Estramustinum; Estramustinum [INN-Latin]; Estramustina [INN-Spanish]; UNII-35LT29625A; Estradiol 3-(N,N-bis(2-chloroethyl)carbamate); 17beta-Estradiol 3-(bis(2-chloroethyl)carbamate); CHEMBL1575; 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]; 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; Estradiol 3-[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-(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
Clinical Status
Approved
Disease Indication Prostate cancer ICD-11: 2C82 [1]
PubChem CID
259331
Formula
C23H31Cl2NO3
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=259331"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 440.4 Topological Polar Surface Area 49.8
XlogP 4 Complexity 585
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Estramustine 140 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Magnesium stearate; Talc; Titanium dioxide; Silicon dioxide
                   Dosage Form Oral Capsule
                   Company Pharmacia and Upjohn Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Estramustine Phosphate Sodium eq 140mg phosphate capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium Stearate; Silicon Dioxide; Sodium Lauryl Sulfate; Talc; Titanium Dioxide
                   Dosage Form Capsule
                   Company Pharmacia And Upjohn Co
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved estramustine from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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