Details of the Drug

General Information of Drug (ID: DM9JXB7)

Drug Name
Retapamulin
Synonyms Altabax; Altargo; SB 275833; Altabax (Glaxo); Altabax (TN); Altargo (TN); Retapamulin (USAN/INN)
Indication
Disease Entry ICD 11 Status REF
Impetigo 1B72 Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 517.799
Topological Polar Surface Area (xlogp) 6.1
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Metabolism
The drug is metabolized via the liver [2]
Chemical Identifiers
Formula
C30H47NO4S
IUPAC Name
[(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,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
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)CSC4C[C@H]5CC[C@@H](C4)N5C)C
InChI
InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1
InChIKey
STZYTFJPGGDRJD-FJJJPKKESA-N
Cross-matching ID
PubChem CID
6918462
ChEBI ID
CHEBI:166679
CAS Number
224452-66-8
DrugBank ID
DB01256
TTD ID
D03UQM

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA) TTUWYEA NOUNIPROTAC Inhibitor [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Retapamulin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Posaconazole DMUL5EW Minor Decreased metabolism of Retapamulin caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [13]
Dalfopristin DM4LTKV Minor Decreased metabolism of Retapamulin caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [13]
Troleandomycin DMUZNIG Minor Decreased metabolism of Retapamulin caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [13]
Pexidartinib DMS2J0Z Moderate Increased metabolism of Retapamulin caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [14]
Lapatinib DM3BH1Y Minor Decreased metabolism of Retapamulin caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [13]
Tucatinib DMBESUA Minor Decreased metabolism of Retapamulin caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [13]
Osilodrostat DMIJC9X Minor Decreased metabolism of Retapamulin caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [13]
MK-8228 DMOB58Q Minor Decreased metabolism of Retapamulin caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [13]
Stiripentol DMMSDOY Minor Decreased metabolism of Retapamulin caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [13]
Fosamprenavir DM4W9B3 Minor Decreased metabolism of Retapamulin caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [13]
Cobicistat DM6L4H2 Minor Decreased metabolism of Retapamulin caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [13]
Darunavir DMN3GCH Minor Decreased metabolism of Retapamulin caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [13]
Berotralstat DMWA2DZ Minor Decreased metabolism of Retapamulin caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [13]
Ceritinib DMB920Z Minor Decreased metabolism of Retapamulin caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [13]
Selpercatinib DMZR15V Minor Decreased metabolism of Retapamulin caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [13]
Idelalisib DM602WT Minor Decreased metabolism of Retapamulin caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [13]
IPI-145 DMWA24P Minor Decreased metabolism of Retapamulin caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [13]
Danazol DML8KTN Minor Decreased metabolism of Retapamulin caused by Danazol mediated inhibition of CYP450 enzyme. Menstrual cycle bleeding disorder [GA20] [13]
Fedratinib DM4ZBK6 Minor Decreased metabolism of Retapamulin caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [13]
Netupitant DMEKAYI Minor Decreased metabolism of Retapamulin caused by Netupitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [13]
Entrectinib DMMPTLH Minor Decreased metabolism of Retapamulin caused by Entrectinib mediated inhibition of CYP450 enzyme. Non-small cell lung cancer [2C25] [13]
Rucaparib DM9PVX8 Minor Decreased metabolism of Retapamulin caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [13]
Abametapir DM2RX0I Moderate Decreased metabolism of Retapamulin caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [15]
Lonafarnib DMGM2Z6 Minor Decreased metabolism of Retapamulin caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [13]
Voxelotor DMCS6M5 Minor Decreased metabolism of Retapamulin caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [13]
Larotrectinib DM26CQR Minor Decreased metabolism of Retapamulin caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [13]
LEE011 DMMX75K Minor Decreased metabolism of Retapamulin caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [13]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Retapamulin caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [16]
⏷ Show the Full List of 28 DDI Information of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 022055.
2 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
3 Retapamulin inhibition of translation and 50S ribosomal subunit formation in Staphylococcus aureus cells. Antimicrob Agents Chemother. 2007 Sep;51(9):3385-7.
4 A synthetic alanyl-initiator tRNA with initiator tRNA properties as determined by fluorescence measurements: comparison to a synthetic alanyl-elongator tRNA. Nucleic Acids Res. 1991 Oct 25;19(20):5749-54.
5 An examination of the differential sensitivity to ketolide antibiotics in ermB strains of Streptococcus pyogenes and Streptococcus pneumoniae. Curr Microbiol. 2004 Oct;49(4):239-47.
6 Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21.
7 Review of macrolides and ketolides: focus on respiratory tract infections. Drugs. 2001;61(4):443-98.
8 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
9 Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5.
10 The streptogramin antibiotics: update on their mechanism of action. Expert Opin Investig Drugs. 1998 Apr;7(4):591-9.
11 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
12 The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo. J Mol Biol. 2002 Sep 13;322(2):273-9.
13 Product Information. Altabax (retapamulin topical). GlaxoSmithKline, Research Triangle Park, NC.
14 Product Information. Sonata (zaleplon) Wyeth-Ayerst Laboratories, Philadelphia, PA.
15 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
16 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.