Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01201)
Name
Lefamulin
Synonyms    Click to Show/Hide the Synonyms of This API
Lefamulin; CHEMBL3291398; 1061337-51-6; 1061337-51-6 (free base); BC-3781; (3aR,4R,5R,7S,8S,9R,9aS,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-(((1R,2R,4R)-4-amino-2-hydroxycyclohexyl)thio)acetate; Lefamulin(BC-3781); Xenleta; Lefamulin (USAN/INN); SCHEMBL19766421; GTPL10824; EX-A3600; BC3781; BDBM50019649; compound 7 [PMID: 24874438]; D11631; Q27253537; UNII-61H04Z5F9K component KPVIXBKIJXZQJX-FCEONZPQSA-N; (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanyl}acetate; [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanylacetate; 62B
Clinical Status
Approved
PubChem CID
25185057
Formula
C28H45NO5S
Canonical SMILES
C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CS[C@@H]4CC[C@H](C[C@H]4O)N)C
InChI
1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1
InChIKey
KPVIXBKIJXZQJX-FCEONZPQSA-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=25185057"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 507.7 Topological Polar Surface Area 135
XlogP 4.3 Complexity 851
Heavy Atom Count 35 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Lefamulin 600 mg tablet 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
Colloidal Silicon Dioxide; Croscarmellose Sodium; Fd&C Blue No 2 Aluminum Lake; Ferrosoferric Oxide; Magnesium Stearate; Mannitol; Microcrystalline Cellulose; Polyethylene Glycol; Polyvinyl Alcohol (Partially Hydrolyzed); Povidone K30; Shellac Glaze; Talc; Titanium Dioxide
                   Dosage Form Tablet
                   Company Nabriva Therapeutics Us
                   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) [1]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
          Lefamulin 150 mg Injection 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 Chloride; Water For Injection; Citric Acid Anhydrous; Sodium Chloride; Trisodium Citrate Dihydrate; Water For Injection
                   Dosage Form Injection
                   Company Nabriva Therapeutics Us
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [6]
References
1 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
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.
6 PubChem BioAssay data set.

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