Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00423)
Name
Metolazone
Synonyms    Click to Show/Hide the Synonyms of This API
metolazone; 17560-51-9; Zaroxolyn; Mykrox; Microx; Metalozone; Metenix; Oldren; 7-Chloro-2-methyl-4-oxo-3-(o-tolyl)-1,2,3,4-tetrahydroquinazoline-6-sulfonamide; Metolazona; Metolazonum; Metolazonum [INN-Latin]; Metolazona [INN-Spanish]; SR 720-22; SR-720-22; Metolazone (Zaroxolyn); 2-Methyl-3-o-tolyl-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinone; 7-Chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-6-quinazolinesulfonamide; 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide; UNII-NM7V2Y3G0U; NM7V2Y3G0U; UNII-NN9U607695; CHEBI:64354; 6-Quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-; MFCD00069304; NN9U607695; NCGC00093985-07; Metalazone; 6-Quinazolinesulfonamide, 1,2,3,4-tetrahydro-7-chloro-2-methyl-4-oxo-3-o-tolyl-; DSSTox_CID_25167; DSSTox_RID_80717; DSSTox_GSID_45167; Zaroxolyn (TN); SMR001230730; HSDB 3367; SR-05000001765; EINECS 241-539-3; BRN 0965506; Metolazone (JAN/USP/INN); Prestwick_333; CAS-17560-51-9; Metolazone, (+)-; Metolazone, (-)-; Metolazone [USAN:USP:INN:BAN:JAN]; Metolazone(Zaroxolyn)/; Spectrum_000456; Prestwick0_000112; Prestwick1_000112; Prestwick2_000112; Prestwick3_000112; Spectrum2_001741; Spectrum4_000229; Spectrum5_001237; CHEMBL878; (non-labelled)Metolazone-d7; SCHEMBL40558; BSPBio_000124; BSPBio_002422; KBioGR_000897; KBioSS_000936; 5-25-09-00212 (Beilstein Handbook Reference); MLS002153316; MLS002154200; DivK1c_000275; SPECTRUM2300325; SPBio_001842; SPBio_002063; BPBio1_000138; GTPL4838; DTXSID6045167; BDBM25899; HMS500N17; KBio1_000275; KBio2_000936; KBio2_003504; KBio2_006072; NINDS_000275; BCPP000166; HMS1568G06; HMS1922L16; HMS2093P14; HMS2095G06; HMS2230J15; HMS3261J22; HMS3373C11; HMS3655M09; HMS3712G06; HMS3744I19; Pharmakon1600-02300325; BCP21574; EBD54305; HY-B0209; Tox21_110186; Tox21_113526; Tox21_500610; 2-BROMO-5-NITRONICOTINICACID; ABP000634; ANW-46001; CCG-39450; NSC759581; AKOS015897109; Metolazone, >=98% (HPLC), solid; Tox21_110186_1; BCP9000920; DB00524; KS-5139; LP00610; NSC-759581; SDCCGSBI-0051460.P003; IDI1_000275; NCGC00093985-01; NCGC00093985-02; NCGC00093985-03; NCGC00093985-04; NCGC00093985-05; NCGC00093985-06; NCGC00093985-08; NCGC00093985-10; NCGC00093985-11; NCGC00093985-20; NCGC00261295-01; AS-13016; SBI-0051460.P002; AB0012835; DB-044227; AB00052055; SW196612-3; D00431; 7-chloro-2-methyl-4-oxo-3-o-tolyl-1,2,3,4; AB00052055-08; AB00052055_09; AB00052055_10; 560M519; Q-201399; Q1169561; SR-05000001765-1; SR-05000001765-4; SR-05000001765-7; BRD-A61793559-001-05-7; BRD-A61793559-001-08-1; Metolazone, European Pharmacopoeia (EP) Reference Standard; Metolazone, United States Pharmacopeia (USP) Reference Standard; 56436-31-8; 56436-32-9
Clinical Status
Approved
Disease Indication Congestive heart failure ICD-11: BD10 [1]
PubChem CID
4170
Formula
C16H16ClN3O3S
Canonical SMILES
CC1NC2=CC(=C(C=C2C(=O)N1C3=CC=CC=C3C)S(=O)(=O)N)Cl
InChI
1S/C16H16ClN3O3S/c1-9-5-3-4-6-14(9)20-10(2)19-13-8-12(17)15(24(18,22)23)7-11(13)16(20)21/h3-8,10,19H,1-2H3,(H2,18,22,23)
InChIKey
AQCHWTWZEMGIFD-UHFFFAOYSA-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=4170"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 365.8 Topological Polar Surface Area 101
XlogP 4.1 Complexity 594
Heavy Atom Count 24 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Metolazone 10 mg tablet Click to Show/Hide the Full List of Formulation(s):          4 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
D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Carilion Materials Management
                   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]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate 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
D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   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]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide 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
D&c yellow no. 10; Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Eon Labs; 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]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 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
Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Upstate Pharma
                   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]
          Metolazone 2.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          4 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
D&c red no. 30; Fd&c blue no. 2; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Eon Labs; NCS HealthCare of KY, Inc dba Vangard Labs; 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]
D&C red no. 30 DIG Info Heat shock factor 1 (EC50 = 9054 nM) [5]
Magnesium stearate 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
Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Cardinal Health; Mylan Pharamceuticals; NCS HealthCare of KY, Inc dba Vangard Labs
                   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]
Silicon dioxide 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
Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Mylan Pharamceuticals
                   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]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 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
D&c red no. 33; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Carilion Materials Management
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Metolazone 5 mg tablet Click to Show/Hide the Full List of Formulation(s):          5 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
Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Cardinal Health; Mylan Pharamceuticals; NCS HealthCare of KY, Inc dba Vangard Labs
                   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]
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
Fd&c yellow no. 6; Magnesium stearate; Silicon dioxide; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Mylan Pharamceuticals
                   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]
Silicon dioxide 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
Fd&c blue no. 2; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Eon Labs; McKesson; 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]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 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
Fd&c blue no. 2; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company NCS HealthCare of KY, Inc dba Vangard Labs
                   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]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 5 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
Fd&c blue no. 2; Magnesium stearate; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Unither Manufacturing; Upstate 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]
References
1 FDA label for approved metolazone 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.
5 PubChem BioAssay data set.

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