Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01263)
Name
Mupirocin
Synonyms    Click to Show/Hide the Synonyms of This API
Mupirocin; 12650-69-0; Pseudomonic acid; Bactroban; Mupirocine; Centany; Pseudomonic acid A; Mupirocina; Mupirocinum; BRL 4910A; BRL-4910A; UNII-D0GX863OA5; 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid; Bactroban (TN); CHEMBL719; CHEBI:7025; D0GX863OA5; MRC; Bactoderm; 6-Chloro-2,4-dimethoxy pyrimidine; MFCD01711620; NCGC00164554-03; Plasimine; mupirocin calcium salt; 9-(((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid; L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)-; Mupirocine [French]; Mupirocinum [Latin]; Mupirocina [Spanish]; C26H44O9; Bactroban Ointment; BRL-4910F; 80558-54-9; Centany (TN); trans-Pseudomonic acid; Mupirocin Neo-Sensitabs; Mupirocin (USP/INN); SR-05000001947; 115074-43-6; 1jzs; Mupirocin [USAN:USP:INN:BAN]; Mupirocin,(S); 9-((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; mupirocin lithium salt; CPD000471888; 73346-79-9; SCHEMBL3291; DSSTox_CID_26438; DSSTox_RID_81614; DSSTox_GSID_46438; 8-Carboxyoctyl (E)-4-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)-3-methylcrotonat; MLS001074711; BIDD:GT0320; Mupirocin, Pseudomonic Acid A; cid_446596; SCHEMBL1027618; Pseudomonic acid A lithium salt; DTXSID0046438; CHEBI:94519; GTPL10916; AOB6353; HMS2234E20; HMS3259L05; HMS3712K03; Pharmakon1600-01505706; HY-B0958; ZINC4102194; Tox21_112183; BDBM50290686; MFCD11977847; NSC759182; NSC815348; AKOS015994756; Mupirocin, >=92% (HPLC), powder; CCG-213522; DB00410; KS-5137; NC00620; NSC-759182; NSC-815348; NCGC00164554-05; NCGC00164554-06; (E)-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl)tetrahydro-3,4-dihydroxy-beta-methyl-2H-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid; AS-11580; SMR000471888; SBI-0206892.P001; AB0010371; CAS-12650-69-0; M2955; S4297; C11758; D01076; M-8680; AB01563109_01; Mupirocin, Antibiotic for Culture Media Use Only; Q413578; SR-05000001947-1; SR-05000001947-2; BRD-K15262564-001-06-9; Mupirocin, United States Pharmacopeia (USP) Reference Standard; 5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester; 9-((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)-tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)-nonanoic acid; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)oxiranylmethyl]tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)nonanoic acid calcium salt; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)oxiranylmethyl]tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)nonanoic acid lithium salt; 9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid; 9-(4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)-tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; 9-(4-{3,4-Dihydroxy-5-[3-(2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)-nonanoic acid (Mupirocin); 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3- [(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl] oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid; 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methyl-propyl]oxiran-2-yl]methyl]tetrahydropyran-2-yl]-3-methyl-but-2-enoyl]oxynonanoic acid; 9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid; Nonanoic acid, 9-((3-methyl-1-oxo-4-(tetrahydro-3,4-dihydroxy-5-((3-(2-hydroxy-1-methylpropyl)oxiranyl)methyl)-2H-pyran-2-yl)-2-butenyl)oxy)-, (2S-(2alpha(E),3beta,4beta,5alpha(2R*,3R*(1R*,2R*))))-; rel-9-(((E)-4-((2S,3R,4R,5S)-3,4-Dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid
Clinical Status
Approved
PubChem CID
446596
Formula
C26H44O9
Canonical SMILES
C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
InChI
1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1
InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-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=446596"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 500.6 Topological Polar Surface Area 146
XlogP 3 Complexity 694
Heavy Atom Count 35 Rotatable Bond Count 17
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Mupirocin eq 2% base cream 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; Cetomacrogol 1000; Cetyl Alcohol; Mineral Oil; Phenoxyethanol; Purified Water; Stearyl Alcohol; Xanthan Gum
                   Dosage Form Cream
                   Company Glaxosmithkline
                   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]
Cetyl alcohol DIG Info Breast cancer FM3A cells (EC50 = 1600 nM) [2]
Polyoxyl 20 cetyl ether DIG Info Cholesterol 25-hydroxylase (EC50 = 211.5 uM) [3]
          Mupirocin 2% ointment 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
Polyethylene Glycol 400; Polyethylene Glycol 3350
                   Dosage Form Ointment
                   Company Glaxosmithkline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
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 Synthesis and notable antimalarial activity of acyclic peroxides, L-(alkyldioxy)-L-(methyldioxy)cyclododecanes. J Med Chem. 2002 Mar 14; 45(6):1374-8.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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