Details of the Drug

General Information of Drug (ID: DMRD1QK)

Drug Name
Netilmicin
Synonyms
NTL; Netilmicina; Netilmicine; Netilmicinum; Netilyn; Netira; Nettacin; Vectacin; NETILMICIN SULFATE; Sch 20569; Netilmicin (INN); Netilmicin [INN:BAN]; Netilmicina [INN-Spanish]; Netilmicine [INN-French]; Netilmicinum [INN-Latin]; Netira (TN); Nettacin (TN); Sch-20569; O-(2,6-Diamino-2,3,4,6-tetradesoxy-alpha-glycero-4-hexenopyranosyl-(1-4)-O-(3-desoxy-4-C-methyl-3-methylamino-beta-L-arabinopyranosyl-(1-6)-2-desoxy-N1-ethyl-D-streptamin; (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3S,4S,5S)-2-[(1S,2R,3S,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; 1-N-Aethylsisomicin; 1-N-Ethylsisomicin; 2-[4-amino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; 4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01GB07: Netilmicin
J01GB: Other aminoglycosides
J01G: AMINOGLYCOSIDE ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01GB07: Netilmicin
J01GB: Other aminoglycosides
J01G: AMINOGLYCOSIDE ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
S01AA23: Netilmicin
S01AA: Antibiotics
S01A: ANTIINFECTIVES
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 475.6
Logarithm of the Partition Coefficient (xlogp) -4.2
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.55 mL/min/kg [3]
Elimination
85% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 12.616 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.073 L/kg [3]
Chemical Identifiers
Formula
C21H41N5O7
IUPAC Name
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Canonical SMILES
CCN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]2[C@@H]([C@H]([C@@](CO2)(C)O)NC)O)O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N
InChI
InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
InChIKey
CIDUJQMULVCIBT-MQDUPKMGSA-N
Cross-matching ID
PubChem CID
441306
ChEBI ID
CHEMBL1572
CAS Number
56391-56-1
UNII
4O5J85GJJB
DrugBank ID
DB00955
TTD ID
D07JZF
INTEDE ID
DR1139
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2) TTQ8KVI F4NA87_STAAU Binder [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
RNA cytidine acetyltransferase (hALP) DEZV4AP NAT10_HUMAN Substrate [6]
Aminoglycoside O-phosphotransferase (aphA6) DEWPAJD KKA6_ACIBA Substrate [7]
Aminoglycoside N-acetyltransferase (aacC2) DEJADS9 AAC6_ACIBA Substrate [7]
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 Same Disease as Netilmicin
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Cefotetan DM07TX3 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefotetan. Bacterial infection [1A00-1C4Z] [8]
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Kanamycin. Bacterial infection [1A00-1C4Z] [9]
Cefprozil DM7DSYP Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefprozil. Bacterial infection [1A00-1C4Z] [8]
Ceftriaxone DMCEW64 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Ceftriaxone. Bacterial infection [1A00-1C4Z] [8]
Streptomycin DME1LQN Moderate Increased risk of ototoxicity by the combination of Netilmicin and Streptomycin. Bacterial infection [1A00-1C4Z] [9]
Cefepime DMHVWIK Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefepime. Bacterial infection [1A00-1C4Z] [8]
Cefpodoxime DMJUNY5 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefpodoxime. Bacterial infection [1A00-1C4Z] [8]
Rabeprazole DMMZXIW Moderate Increased risk of hypomagnesemia by the combination of Netilmicin and Rabeprazole. Bacterial infection [1A00-1C4Z] [10]
Cefazolin DMPDYFR Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefazolin. Bacterial infection [1A00-1C4Z] [8]
Cefoxitin DMY8NC4 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefoxitin. Bacterial infection [1A00-1C4Z] [8]
⏷ Show the Full List of 10 DDI Information of This Drug
Coadministration of a Drug Treating the Disease Different from Netilmicin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Decreased renal excretion of Netilmicin caused by Remdesivir mediated nephrotoxicity. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [9]
Cefuroxime DMSIMD8 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Cefuroxime. Acute bronchitis [CA42] [8]
Framycetin DMF8DNE Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Framycetin. Alcoholic liver disease [DB94] [9]
Inotersen DMJ93CT Major Increased risk of nephrotoxicity by the combination of Netilmicin and Inotersen. Amyloidosis [5D00] [11]
Etidronic acid DM1XHYJ Moderate Increased risk of hypocalcemia by the combination of Netilmicin and Etidronic acid. Bone paget disease [FB85] [12]
Ketoprofen DMRKXPT Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Ketoprofen. Chronic pain [MG30] [13]
Atracurium DM42HXN Major Additive neuromuscular blocking effects by the combination of Netilmicin and Atracurium. Corneal disease [9A76-9A78] [14]
Mivacurium DM473VD Major Additive neuromuscular blocking effects by the combination of Netilmicin and Mivacurium. Corneal disease [9A76-9A78] [14]
Pancuronium DMB0VY8 Major Additive neuromuscular blocking effects by the combination of Netilmicin and Pancuronium. Corneal disease [9A76-9A78] [14]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Netilmicin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [15]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [9]
Balsalazide DM7I1T9 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Balsalazide. Indeterminate colitis [DD72] [16]
Exjade DMHPRWG Major Increased risk of nephrotoxicity by the combination of Netilmicin and Exjade. Mineral absorption/transport disorder [5C64] [17]
Neostigmine DM6T2J3 Moderate Additive neuromuscular blocking effects by the combination of Netilmicin and Neostigmine. Myasthenia gravis [8C6Y] [14]
Carboplatin DMG281S Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Carboplatin. Ovarian cancer [2C73] [18]
Ibuprofen DM8VCBE Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Ibuprofen. Pain [MG30-MG3Z] [13]
Choline salicylate DM8P137 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Choline salicylate. Postoperative inflammation [1A00-CA43] [19]
Everolimus DM8X2EH Major Increased risk of nephrotoxicity by the combination of Netilmicin and Everolimus. Renal cell carcinoma [2C90] [20]
Temsirolimus DMS104F Major Increased risk of nephrotoxicity by the combination of Netilmicin and Temsirolimus. Renal cell carcinoma [2C90] [20]
Salsalate DM13P4C Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Salsalate. Rheumatoid arthritis [FA20] [13]
Oxaprozin DM9UB0P Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Oxaprozin. Rheumatoid arthritis [FA20] [13]
Ifosfamide DMCT3I8 Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Ifosfamide. Solid tumour/cancer [2A00-2F9Z] [9]
Doxacurium DMKE7L9 Major Additive neuromuscular blocking effects by the combination of Netilmicin and Doxacurium. Tonus and reflex abnormality [MB47] [21]
Vecuronium DMP0UK2 Major Additive neuromuscular blocking effects by the combination of Netilmicin and Vecuronium. Tonus and reflex abnormality [MB47] [14]
Olsalazine DMZW9HA Moderate Increased risk of nephrotoxicity by the combination of Netilmicin and Olsalazine. Ulcerative colitis [DD71] [16]
Plazomicin DMKMBES Moderate Increased risk of ototoxicity by the combination of Netilmicin and Plazomicin. Urinary tract infection [GC08] [11]
⏷ Show the Full List of 26 DDI Information of This Drug

References

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2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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5 Ribosomal resistance in the gentamicin producer organism Micromonospora purpurea. Antimicrob Agents Chemother. 1982 Aug;22(2):231-6.
6 Aminoglycoside resistance resulting from tight drug binding to an altered aminoglycoside acetyltransferase. Antimicrob Agents Chemother. 2003 May;47(5):1577-83.
7 Relationship between antimicrobial resistance and aminoglycoside-modifying enzyme gene expressions in Acinetobacter baumannii. Chin Med J (Engl). 2005 Jan 20;118(2):141-5.
8 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
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10 FDA. U.S. Food and Drug Administration "FDA Drug Safety Communication: Low magnesium levels can be associated with long-term use of proton pump inhibitor drugs (PPIs).".
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13 Assael BM, Chiabrando C, Gagliardi L, Noseda A, Bamonte F, Salmona M "Prostaglandins and aminoglycoside nephrotoxicity." Toxicol Appl Pharmacol 78 (1985): 386-94. [PMID: 4049389]
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17 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
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19 Farag MM, Mikhail MR, Abdel-Meguid E, Abdel-Tawab S "Assessment of gentamicin-induced nephrotoxicity in rats treated with low doses of ibuprofen and diclofenac sodium." Clin Sci 91 (1996): 187-91. [PMID: 8795442]
20 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
21 Geha DG, Blitt CD, Moon BJ "Prolonged neuromuscular blockade with pancuronium in the presence of acute renal failure: a case report." Anesth Analg 55 (1976): 343-5. [PMID: 945014]