Details of the Drug

General Information of Drug (ID: DMFDQ3I)

Drug Name
Daptomycin
Synonyms
Dapcin; Daptomicina; Daptomycine; Daptomycinum; LY 146032; LY-146032; LY146032; (2S)-daptomycin; 103060-53-3; C72H101N17O26; Cidecin; Cubicin; DAPTOMYCIN; CHEBI:600103; N-decanoyl-L-tryptophyl-L-asparaginyl-N-[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]-L-alpha-asparagine; SCHEMBL28102
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Skin infection 1F28-1G0Z Investigative [2]
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1620.7
Logarithm of the Partition Coefficient (xlogp) -5.1
Rotatable Bond Count (rotbonds) 35
Hydrogen Bond Donor Count (hbonddonor) 22
Hydrogen Bond Acceptor Count (hbondacc) 28
Chemical Identifiers
Formula
C72H101N17O26
IUPAC Name
(3S)-3-[[(2S)-4-amino-2-[[(2S)-2-(decanoylamino)-3-(1H-indol-3-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-4-oxobutanoic acid
Canonical SMILES
CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
InChI
DOAKLVKFURWEDJ-RWDRXURGSA-N
InChIKey
1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1
Cross-matching ID
PubChem CID
16134395
ChEBI ID
CHEBI:600103
CAS Number
103060-53-3
DrugBank ID
DB00080
INTEDE ID
DR2142
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Dihydropteroate synthetase (Bact folP) TT4ILYC DHPS_ECOLI Binder [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
CDP-alcohol phosphatidyltransferase (pgsA) DE49HWX A0A081Q830_STRMT Substrate [4]
CDP-alcohol phosphatidyltransferase (pgsA) DETMA7Z A0A081R409_STROR Substrate [4]
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 Daptomycin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Phenylbutazone DMAYL0T Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Phenylbutazone. Chronic pain [MG30] [5]
Ketoprofen DMRKXPT Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Ketoprofen. Chronic pain [MG30] [5]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Daptomycin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [6]
Mefenamic acid DMK7HFI Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Mefenamic acid. Female pelvic pain [GA34] [5]
177Lu-DOTATATE DMT8GVU Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and 177Lu-DOTATATE. Hepatitis virus infection [1E50-1E51] [5]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [5]
Meclofenamic acid DM05FXR Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Meclofenamic acid. Inflammatory spondyloarthritis [FA92] [5]
Moxetumomab pasudotox DMN63DZ Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Moxetumomab pasudotox. Mature B-cell leukaemia [2A82] [5]
Rofecoxib DM3P5DA Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Rofecoxib. Osteoarthritis [FA00-FA05] [5]
Valdecoxib DMAY7H4 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Valdecoxib. Osteoarthritis [FA00-FA05] [5]
Diclofenac DMPIHLS Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Diclofenac. Osteoarthritis [FA00-FA05] [5]
Naproxen DMZ5RGV Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Naproxen. Osteoarthritis [FA00-FA05] [5]
Etodolac DM6WJO9 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Etodolac. Pain [MG30-MG3Z] [5]
Ibuprofen DM8VCBE Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Ibuprofen. Pain [MG30-MG3Z] [5]
Nabumetone DMAT2XH Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Nabumetone. Pain [MG30-MG3Z] [5]
Piroxicam DMTK234 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Piroxicam. Pain [MG30-MG3Z] [5]
Ketorolac DMI4EL5 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Ketorolac. Postoperative inflammation [1A00-CA43] [5]
Bromfenac DMKB79O Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Bromfenac. Postoperative inflammation [1A00-CA43] [5]
Meloxicam DM2AR7L Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Meloxicam. Rheumatoid arthritis [FA20] [5]
Sulindac DM2QHZU Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Sulindac. Rheumatoid arthritis [FA20] [5]
Celecoxib DM6LOQU Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Celecoxib. Rheumatoid arthritis [FA20] [5]
Oxaprozin DM9UB0P Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Oxaprozin. Rheumatoid arthritis [FA20] [5]
Fenoprofen DML5VQ0 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Fenoprofen. Rheumatoid arthritis [FA20] [5]
Indomethacin DMSC4A7 Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Indomethacin. Rheumatoid arthritis [FA20] [5]
Tolmetin DMWUIJE Moderate Increased risk of nephrotoxicity by the combination of Daptomycin and Tolmetin. Rheumatoid arthritis [FA20] [5]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Daptomycin due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [6]
⏷ Show the Full List of 26 DDI Information of This Drug

References

1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
2 Daptomycin FDA Label
3 Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin. Chem Biol. 2004 Jul;11(7):949-57.
4 Mutations in cdsA and pgsA correlate with daptomycin resistance in Streptococcus mitis and S. oralis. Antimicrob Agents Chemother. 2019 Jan 29;63(2). pii: e01531-18.
5 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
6 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.