Details of the Drug

General Information of Drug (ID: DMF8DNE)

Drug Name

Framycetin

Synonyms

Neomycin; neomycin; NEOMYCIN B; Soframycin; Actiline; Mycifradin; Fradiomycin; Soframycine; Framycetinum; Framycetine; Framicetina; Neomas; Fradiomycinum; Antibiotique; Nivemycin; Actilin; Neolate; Enterfram; Myacyne; Framygen; Caswell No 595; Vonamycin powder V; Neomycin B sulfate; Neomin; Neomcin; Fradiomycin B; Neo-Rx; Neomicina [DCIT]; Framycetinum [INN-Latin]; PIMAVECORT; Neobrettin; Neo-Fradin; 119-04-0; Neomycine [INN-French]; Neomycinum [INN-Latin]; Framycetine [INN-French]; Framicetina [INN-Spanish]; USAF CB-19; Endomixin; Fraquinol; Myacine; Myciguent; NMY; Neobiotic; Neomicina; Neomycinum; Tuttomycin; VONAMYCIN; NEOMYCIN AND POLYMYXIN B SULFATES; NEOMYCIN SULFATE; Neomycin solution; Soframycin Ophthalmic; Antibiotic 10676; Antibiotic produced by Streptomyces decaris Neomycin B; Framycetin (INN); Soframycin (TN); Framycetin [INN:BAN:DCF]; Sofra-Tulle (TN); BDG-(1-4)CYY-(5-1)RIB-(3-1)IDG; BDG-(1-4)NEB-(5-1)RIB-(3-1)NED; (1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside; (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol; D-Streptamine, O-2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl-(1->3)-O-beta-D-ribofuranosyl-(1->5)]-O-[2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1->4)]-2-deoxy

Indication

Disease Entry	ICD 11	Status	REF
Acute liver failure	DB91	Approved	[1]
Alcoholic cirrhosis of liver	DB94	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Blepharoconjunctivitis	N.A.	Approved	[3]
Corneal abrasion	NA06.4	Approved	[3]
Hepatic coma	N.A.	Approved	[3]
Hepatic encephalopathy	DB99.5	Approved	[3]
Keratitis	N.A.	Approved	[4]
Urinary tract infection	GC08	Approved	[5]
Uveitis	9A96.Z	Investigative	[3]
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⏷ Show the Full List of Indication(s)

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

614.6

Logarithm of the Partition Coefficient (xlogp)

-9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [6]
Elimination: 40% of drug is excreted from urine in the unchanged form [6]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 140.84509 micromolar/kg/day [7]
Water Solubility: The ability of drug to dissolve in water is measured as 6.3 mg/mL [6]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Agitation	Not Available	NAA15	OT53SIZG	[8]
Cell-mediated cytotoxicity	Not Available	GFAP	OTQ01ZAS	[8]
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Chemical Identifiers

Formula: C23H46N6O13
IUPAC Name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
Canonical SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
InChI: InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChIKey: PGBHMTALBVVCIT-VCIWKGPPSA-N

Cross-matching ID

PubChem CID: 8378
ChEBI ID: CHEBI:7508
CAS Number: 119-04-0
DrugBank ID: DB00452
TTD ID: D05JNI
INTEDE ID: DR2158
ACDINA ID: D00462

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 16S ribosomal RNA (Bact 16S rRNA)	TT38DW5	NOUNIPROTAC	Binder	[9]
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2)	TTQ8KVI	F4NA87_STAAU	Binder	[10]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Aminoglycoside O-phosphotransferase (aphA6)	DEWPAJD	KKA6_ACIBA	Substrate	[11]
Aminoglycoside N-acetyltransferase (aacC2)	DEJADS9	AAC6_ACIBA	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Glial fibrillary acidic protein (GFAP)	OTQ01ZAS	GFAP_HUMAN	Drug Response	[8]
N-alpha-acetyltransferase 15, NatA auxiliary subunit (NAA15)	OT53SIZG	NAA15_HUMAN	Drug Response	[8]
T-lymphocyte activation antigen CD86 (CD86)	OTJCSBPC	CD86_HUMAN	Gene/Protein Processing	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Framycetin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Decreased renal excretion of Framycetin caused by Remdesivir mediated nephrotoxicity.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Cefuroxime	DMSIMD8	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefuroxime.	Acute bronchitis [CA42]	[14]
Inotersen	DMJ93CT	Major	Increased risk of nephrotoxicity by the combination of Framycetin and Inotersen.	Amyloidosis [5D00]	[15]
Cefamandole	DMNEXZF	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefamandole.	Anaerobic bacterial infection [1A00-1A09]	[14]
Cefotetan	DM07TX3	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefotetan.	Bacterial infection [1A00-1C4Z]	[14]
Kanamycin	DM2DMPO	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Kanamycin.	Bacterial infection [1A00-1C4Z]	[13]
Ceftizoxime	DM3VOGS	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Ceftizoxime.	Bacterial infection [1A00-1C4Z]	[14]
Cefoperazone	DM53PV8	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefoperazone.	Bacterial infection [1A00-1C4Z]	[14]
Cefprozil	DM7DSYP	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefprozil.	Bacterial infection [1A00-1C4Z]	[14]
Ceftriaxone	DMCEW64	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Ceftriaxone.	Bacterial infection [1A00-1C4Z]	[14]
Streptomycin	DME1LQN	Moderate	Increased risk of ototoxicity by the combination of Framycetin and Streptomycin.	Bacterial infection [1A00-1C4Z]	[13]
Cefepime	DMHVWIK	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefepime.	Bacterial infection [1A00-1C4Z]	[14]
Rabeprazole	DMMZXIW	Moderate	Increased risk of hypomagnesemia by the combination of Framycetin and Rabeprazole.	Bacterial infection [1A00-1C4Z]	[16]
Cefazolin	DMPDYFR	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefazolin.	Bacterial infection [1A00-1C4Z]	[14]
Cefonicid	DMTX2BH	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefonicid.	Bacterial infection [1A00-1C4Z]	[14]
Cefradine	DMUNSWV	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefradine.	Bacterial infection [1A00-1C4Z]	[17]
Cefoxitin	DMY8NC4	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cefoxitin.	Bacterial infection [1A00-1C4Z]	[14]
Etidronic acid	DM1XHYJ	Moderate	Increased risk of hypocalcemia by the combination of Framycetin and Etidronic acid.	Bone paget disease [FB85]	[18]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Framycetin and Iodipamide.	Cholelithiasis [DC11]	[19]
Atracurium	DM42HXN	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Atracurium.	Corneal disease [9A76-9A78]	[20]
Mivacurium	DM473VD	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Mivacurium.	Corneal disease [9A76-9A78]	[20]
Pancuronium	DMB0VY8	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Pancuronium.	Corneal disease [9A76-9A78]	[20]
Tubocurarine	DMBZIVP	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Tubocurarine.	Corneal disease [9A76-9A78]	[20]
Methoxyflurane	DML0RAE	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Methoxyflurane.	Corneal disease [9A76-9A78]	[15]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Framycetin due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[21]
Dexlansoprazole	DM1DBV5	Moderate	Increased risk of hypomagnesemia by the combination of Framycetin and Dexlansoprazole.	Gastro-oesophageal reflux disease [DA22]	[16]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[13]
Balsalazide	DM7I1T9	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Balsalazide.	Indeterminate colitis [DD72]	[22]
Exjade	DMHPRWG	Major	Increased risk of nephrotoxicity by the combination of Framycetin and Exjade.	Mineral absorption/transport disorder [5C64]	[23]
Neostigmine	DM6T2J3	Moderate	Additive neuromuscular blocking effects by the combination of Framycetin and Neostigmine.	Myasthenia gravis [8C6Y]	[20]
Everolimus	DM8X2EH	Major	Increased risk of nephrotoxicity by the combination of Framycetin and Everolimus.	Renal cell carcinoma [2C90]	[24]
Temsirolimus	DMS104F	Major	Increased risk of nephrotoxicity by the combination of Framycetin and Temsirolimus.	Renal cell carcinoma [2C90]	[24]
Cephapirin	DMV2JNY	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Cephapirin.	Sepsis [1G40-1G41]	[17]
Ifosfamide	DMCT3I8	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Ifosfamide.	Solid tumour/cancer [2A00-2F9Z]	[13]
Pipecuronium	DM5F84A	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Pipecuronium.	Tonus and reflex abnormality [MB47]	[20]
Doxacurium	DMKE7L9	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Doxacurium.	Tonus and reflex abnormality [MB47]	[20]
Vecuronium	DMP0UK2	Major	Additive neuromuscular blocking effects by the combination of Framycetin and Vecuronium.	Tonus and reflex abnormality [MB47]	[20]
Olsalazine	DMZW9HA	Moderate	Increased risk of nephrotoxicity by the combination of Framycetin and Olsalazine.	Ulcerative colitis [DD71]	[22]
Plazomicin	DMKMBES	Moderate	Increased risk of ototoxicity by the combination of Framycetin and Plazomicin.	Urinary tract infection [GC08]	[13]
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⏷ Show the Full List of 39 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Calcium stearate	E00244	15324	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Neomycin 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	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. (Ligand id: 709).
2	Drug information of Framycetin, 2008. eduDrugs.
3	A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
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6	BDDCS applied to over 900 drugs
7	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
9	Antistaphylococcal activity of gentamicin. Minerva Med. 1975 Dec 8;66(84):4505-26.
10	Characterization of a 30S ribosomal subunit assembly intermediate found in Escherichia coli cells growing with neomycin or paromomycin. Arch Microbiol. 2008 May;189(5):441-9.
11	Relationship between antimicrobial resistance and aminoglycoside-modifying enzyme gene expressions in Acinetobacter baumannii. Chin Med J (Engl). 2005 Jan 20;118(2):141-5.
12	A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals. Toxicology. 2009 Oct 1;264(1-2):1-9. doi: 10.1016/j.tox.2009.07.021. Epub 2009 Aug 7.
13	Cerner Multum, Inc. "Australian Product Information.".
14	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
15	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
16	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).".
17	Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]
18	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]
19	Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
20	Burkett L, Bikhazi GB, Thomas KC Jr, Rosenthal DA, Wirta MG, Foldes FF "Mutual potentiation of the neuromuscular effects of antibiotics and relaxants." Anesth Analg 58 (1979): 107-15. [PMID: 571233]
21	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
22	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]
23	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
24	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.