Details of the Drug

General Information of Drug (ID: DM5OHYE)

Drug Name
Bacitracin
Synonyms
Altracin; Baciguent; Baciquent; Citracin; Fortracin; Bacitracin A; Bacitracin A1; Bacitracin A2a; Neosporin (TN); Solu-Tracin 50; Partyl-, (10.4)-lactam; L-Asparagine, N-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-4-thiazolyl]carbonyl]-L-leucyl-D-.alpha.-glutamyl-L-isoleucyl-L-lysyl-D-ornithyl-L-isoleucyl-D-phenylalanyl-L-histidyl-D-.alpha.-as; 11702_FLUKA; 11702_SIGMA
Indication
Disease Entry ICD 11 Status REF
Skin infection 1F28-1G0Z Approved [1], [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1422.7
Topological Polar Surface Area (xlogp) -4.1
Rotatable Bond Count (rotbonds) 31
Hydrogen Bond Donor Count (hbonddonor) 17
Hydrogen Bond Acceptor Count (hbondacc) 21
Chemical Identifiers
Formula
C66H103N17O16S
IUPAC Name
(4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES
CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
InChI
InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
InChIKey
CLKOFPXJLQSYAH-ABRJDSQDSA-N
Cross-matching ID
PubChem CID
10909430
ChEBI ID
CHEBI:35862
CAS Number
1405-87-4
DrugBank ID
DB00626
TTD ID
D0M1IO

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Insulin-degrading enzyme (IDE) TT2EDHU IDE_HUMAN 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 Bacitracin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Decreased renal excretion of Bacitracin caused by Remdesivir mediated nephrotoxicity. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [7]
Inotersen DMJ93CT Major Increased risk of nephrotoxicity by the combination of Bacitracin and Inotersen. Amyloidosis [5D00] [8]
Etidronic acid DM1XHYJ Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Etidronic acid. Bone paget disease [FB85] [9]
Iodipamide DMXIQYS Major Increased risk of nephrotoxicity by the combination of Bacitracin and Iodipamide. Cholelithiasis [DC11] [10]
Atracurium DM42HXN Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Atracurium. Corneal disease [9A76-9A78] [11]
Mivacurium DM473VD Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Mivacurium. Corneal disease [9A76-9A78] [11]
Pancuronium DMB0VY8 Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Pancuronium. Corneal disease [9A76-9A78] [11]
Tubocurarine DMBZIVP Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Tubocurarine. Corneal disease [9A76-9A78] [11]
Mycophenolic acid DMU65NK Moderate Altered absorption of Bacitracin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [12]
Balsalazide DMO091F Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Balsalazide. Indeterminate colitis [DD72] [13]
Ibandronate DM0QZBN Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Ibandronate. Low bone mass disorder [FB83] [14]
Clofarabine DMCVJ86 Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Clofarabine. Mature B-cell lymphoma [2A85] [15]
Exjade DMHPRWG Major Increased risk of nephrotoxicity by the combination of Bacitracin and Exjade. Mineral absorption/transport disorder [5C64] [16]
Pemetrexed DMMX2E6 Moderate Decreased renal excretion of Bacitracin caused by Pemetrexed mediated nephrotoxicity. Pleural mesothelioma [2C26] [17]
Everolimus DM8X2EH Major Increased risk of nephrotoxicity by the combination of Bacitracin and Everolimus. Renal cell carcinoma [2C90] [18]
Temsirolimus DMS104F Major Increased risk of nephrotoxicity by the combination of Bacitracin and Temsirolimus. Renal cell carcinoma [2C90] [18]
Sulfasalazine DMICA9H Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Sulfasalazine. Rheumatoid arthritis [FA20] [13]
Pipecuronium DM5F84A Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Pipecuronium. Tonus and reflex abnormality [MB47] [11]
Doxacurium DMKE7L9 Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Doxacurium. Tonus and reflex abnormality [MB47] [11]
Vecuronium DMP0UK2 Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Vecuronium. Tonus and reflex abnormality [MB47] [11]
Rocuronium DMY9BMK Moderate Additive neuromuscular blocking effects by the combination of Bacitracin and Rocuronium. Tonus and reflex abnormality [MB47] [11]
Sirolimus DMGW1ID Major Increased risk of nephrotoxicity by the combination of Bacitracin and Sirolimus. Transplant rejection [NE84] [18]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Bacitracin due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [12]
Tacrolimus DMZ7XNQ Major Increased risk of nephrotoxicity by the combination of Bacitracin and Tacrolimus. Transplant rejection [NE84] [18]
Olsalazine DMZW9HA Moderate Increased risk of nephrotoxicity by the combination of Bacitracin and Olsalazine. Ulcerative colitis [DD71] [13]
⏷ Show the Full List of 25 DDI Information of This Drug

References

1 Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Brain insulin impairs amyloid-beta(1-40) clearance from the brain. J Neurosci. 2004 Oct 27;24(43):9632-7.
4 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2371).
5 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
6 Dual Exosite-binding Inhibitors of Insulin-degrading Enzyme Challenge Its Role as the Primary Mediator of Insulin Clearance in Vivo. J Biol Chem. 2015 Aug 14;290(33):20044-59.
7 Cerner Multum, Inc. "Australian Product Information.".
8 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
9 Chang JT, Green L, Beitz J "Renal failure with the use of zoledronic acid." N Engl J Med 349 (2003): 1676-9 discussion 1676-9. [PMID: 14573746]
10 Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
11 Huang KC, Heise A, Shrader AK, Tsueda K "Vancomycin enhances the neuromuscular blockade of vecuronium." Anesth Analg 71 (1990): 194-6. [PMID: 1973882]
12 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
13 Novis BH, Korzets Z, Chen P, Bernheim J "Nephrotic syndrome after treatment with 5-aminosalicylic acid." Br Med J (Clin Res Ed) 296 (1988): 1442. [PMID: 3132281]
14 Banerjee D, Asif A, Striker L, Preston RA, Bourgoignie JJ, Roth D "Short-term, high-dose pamidronate-induced acute tubular necrosis: The postulated mechanisms of bisphosphonate nephrotoxicity." Am J Kidney Dis 41 (2003): E18. [PMID: 12778436]
15 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
16 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
17 Product Information. Alimta (pemetrexed). Lilly, Eli and Company, Indianapolis, IN.
18 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.