Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00849)
Name
Atovaquone
Synonyms    Click to Show/Hide the Synonyms of This API
ATOVAQUONE; 95233-18-4; Mepron; Wellvone; Acuvel; Atavaquone; 566C80; Mepron (antipneumocystic); 94015-53-9; cis-Atovaquone; BW 566C; 566C; C22H19ClO3; 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione; Atovaquone (Atavaquone); 137732-39-9; 2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; UNII-Y883P1Z2LT; UNII-F1W7QUV0KI; F1W7QUV0KI; 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione; 2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE; CHEMBL519462; Y883P1Z2LT; CHEBI:575568; 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione; NCGC00016961-01; CAS-95233-18-4; 2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione; DSSTox_CID_2629; DSSTox_RID_76664; DSSTox_GSID_22629; 2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; 1,4-Naphthalenedione, 2-[cis-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-; 2-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione; DRG-0084; BW 566C-80; Mepron (TN); BW-A 566C; HSDB 7083; SR-05000001438; BW-566C-80; CRL-8131 & Atovaquone; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; Atovaquone & Interleukin 12; 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-naphthalene-1,4-dione; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione; cis-2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; Cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; 1,4-Naphthalenedione, 2-(cis-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-; 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione; trans-2-(4-(4-chlorophenyl) cyclohexyl)-3-hydroxynaphthalene-1,4-dione; ATO & IL-12; Atovaquone [USAN:USP:INN:BAN]; Atovaquone-[d5]; BW 566C80; 1329792-63-3; Spectrum_001743; SpecPlus_000686; Prestwick0_000534; Prestwick1_000534; Prestwick2_000534; Prestwick3_000534; Spectrum2_001665; Spectrum3_000991; Spectrum4_001117; Spectrum5_001382; Atovaquone EP Impurity B; SCHEMBL21694; SCHEMBL21695; Atovaquone (JAN/USP/INN); BSPBio_000547; BSPBio_002681; KBioGR_001594; KBioSS_002223; Atovaquone Related Compound A; MLS002153863; BIDD:GT0849; DivK1c_006782; SCHEMBL637069; SPECTRUM1504210; SPBio_001849; SPBio_002468; BPBio1_000603; CHEMBL222334; CHEMBL471792; GTPL9695; NAP016; SCHEMBL1542719; SCHEMBL1649508; SCHEMBL9975142; SCHEMBL9975229; Atovaquone, >=98% (HPLC); DTXSID7022629; CHEBI:95346; KBio1_001726; KBio2_002223; KBio2_004791; KBio2_007359; KBio3_001901; DTXSID20916694; BDBM192009; HMS1569L09; HMS1922F19; HMS2089M14; HMS2093C10; HMS2096L09; HMS2235N08; HMS3369N09; HMS3651N20; HMS3713L09; Pharmakon1600-01504210; AMY15339; BCP09477; Tox21_110714; 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-naphthalene-1,2-dione; Atovaquone related compound A [USP]; CCG-39090; FD7252; MFCD00889188; NSC759582; s3079; STK636160; trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; ZINC12504271; 1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-, trans-; 1,4-Naphthalenedione, 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione; AKOS005567953; AKOS015895691; AKOS015961933; Tox21_110714_1; ZINC100017856; ZINC100345537; ZINC116473771; ZINC299873031; BW-556C-80; CCG-220534; DB01117; MCULE-7318126574; NSC-759582; NCGC00016961-02; NCGC00016961-03; NCGC00016961-04; NCGC00016961-06; NCGC00016961-07; NCGC00095113-01; NCGC00095113-02; AC-30251; AK544285; AS-12809; Atovaquone 100 microg/mL in Acetonitrile; HY-13832; SMR001233220; SBI-0052893.P002; AB0012456; AB0107187; AB0211463; AB00513855; FT-0602868; SW219222-1; A13708; C06835; D00236; J90007; 78668-EP2307343A1; AB00053222-03; AB00053222_04; AB00053222_05; 233A184; Q418179; SR-05000001438-1; SR-05000001438-2; SR-05000001438-4; SR-05000001438-5; Z1541632806; 2-[4-(4-chlorophenyl)cyclohexy]-3-hydroxy-1,4-naphthoquinone; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-napthoquinone; 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1.4-naphthoquinone; 2-Hydroxy-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone; 3-[4-(p-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthoquinone; 1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-; 2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxynaphthoquinone, trans-; 3-[4-(4-Chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthalenedione; 1,4-Naphthalenedione, 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy; 2-(cis-4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione; cis -2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione; 2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione
Clinical Status
Approved
PubChem CID
74989
Formula
C22H19ClO3
Canonical SMILES
C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
InChI
1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,24H,5-8H2
InChIKey
BSJMWHQBCZFXBR-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL 2D MOL
Physicochemical Properties Molecular Weight 366.8 Topological Polar Surface Area 54.4
XlogP 5.2 Complexity 595
Heavy Atom Count 26 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Atovaquone 750mg/5ml suspension 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
Benzyl Alcohol; Flavor; Hypromellose; Poloxamer; Purified Water; Saccharin Sodium; Xanthan Gum
                   Dosage Form Suspension
                   Company Major Pharmaceuticals; Pharmaceutical Associates
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [1]
Saccharin sodium anhydrous DIG Info Carbonic anhydrase I (Ki = 18540 nM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [3]
References
1 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
2 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15; 17(14):5054-8.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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