Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00249)
Name
Estropipate
Synonyms    Click to Show/Hide the Synonyms of This API
Estropipate; 7280-37-7; Piperazine estrone sulfate; Piperazine estronesulfate; UNII-SVI38UY019; SVI38UY019; Harmogen; Estra-1,3,5(10)-trien-17-one, 3-(sulfooxy)-, compd. with piperazine (1:1); Ortho-Est; Sulestrex; piperazine (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl sulfate; OGEN 5; Estropipate [USP:INN:BAN]; OGEN 2.5; OGEN .625; OGEN 1.25; EINECS 230-696-3; Estropipate (USP); Ogen (TN); PubChem22728; NCGC00016682-02; DSSTox_CID_3005; CAS-7280-37-7; Piperazine oestrone sulphate; Conjugated estrogens: piperazine estrone sulfate; DSSTox_RID_76828; DSSTox_GSID_23005; SCHEMBL21577; MLS002153957; CHEBI:4873; CHEMBL1200980; DTXSID3023005; Estrone hydrogen sulfate compound with piperazine (1:1); HMS1570I17; HMS2097I17; HMS2232O19; HMS3714I17; BCP05424; HY-B1361; Tox21_113350; MFCD00867399; AKOS024457702; Estra-1,3,5(10)-trien-17-one 3-sulphate, compound with piperazine (1:1); BCP9000662; CCG-220688; CM14419; CS-4818; Estropipate, >=98% (HPLC), powder; SMR001233296; AM20080957; D00948; 280E377; A837628; SR-01000000235; Q5401860; SR-01000000235-5; Piperazine, compd. with estrone hydrogen sulfate (1:1) (8CI); Estrone, hydrogen sulfate, compd. with piperazine (1:1) (8CI); Estropipate, United States Pharmacopeia (USP) Reference Standard; 17-oxoestra-1,3,5(10)-trien-3-yl hydrogen sulfate - piperazine (1:1); Piperazine, compd. with 3-(sulfooxy)estra-1,3,5(10)-trien-17-one (1:1) (9CI); [(8R,9S,13S,14S)-13-methyl-17-oxidanylidene-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate; piperazine; [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate,piperazine; piperazine; sulfuric acid [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] ester
Clinical Status
Approved
Disease Indication Hypogonadism ICD-11: 5A61 [1]
PubChem CID
5284555
Formula
C22H32N2O5S
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)O.C1CNCCN1
InChI
1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
InChIKey
HZEQBCVBILBTEP-ZFINNJDLSA-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=5284555"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 436.6 Topological Polar Surface Area 113
XlogP N.A. Complexity 650
Heavy Atom Count 30 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Estropipate 0.75 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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
Lactose monohydrate; D&c yellow no. 10; Fd&c yellow no. 6; Magnesium stearate; Crospovidone; Silicon dioxide; Aluminum oxide; Starch, corn
                   Dosage Form Oral Tablet
                   Company Barr Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 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
Lactose; D&c yellow no. 10; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actavis Pharma; Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 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
Lactose; D&c yellow no. 10; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Estropipate 1.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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
Lactose monohydrate; Fd&c yellow no. 6; Magnesium stearate; Crospovidone; Silicon dioxide; Aluminum oxide; Starch, corn
                   Dosage Form Oral Tablet
                   Company Barr Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 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
Lactose; Fd&c yellow no. 6; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actavis Pharma; Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 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
Lactose; Fd&c yellow no. 6; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Estropipate 3 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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
Lactose monohydrate; Fd&c blue no. 2; Magnesium stearate; Crospovidone; Silicon dioxide; Aluminum oxide; Starch, corn
                   Dosage Form Oral Tablet
                   Company Barr Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 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
Lactose; Fd&c blue no. 2; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 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
Lactose; Fd&c blue no. 2; Magnesium stearate; Talc; Piperazine; Starch, corn
                   Dosage Form Oral Tablet
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved estropipate 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 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 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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