Identification
- Summary
Apramycin is an aminoglycoside antibiotic for veterinary use that is used to treat infections in animals.
- Generic Name
- Apramycin
- DrugBank Accession Number
- DB04626
- Background
Apramycin is an aminoglycoside antibiotic and has a bactericidal action against many gram-negative bacteria. Apramycin is a structurally unique antibiotic that contains a bicyclic sugar moiety and a monosubstituted deoxystreptamine. It is not approved for use in humans.
- Type
- Small Molecule
- Groups
- Experimental, Vet approved
- Structure
Structure for Apramycin (DB04626)
- Weight
- Average: 539.5771
Monoisotopic: 539.280257179 - Chemical Formula
- C21H41N5O11
- Synonyms
- 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine
- 4-O-(3α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5aβ,6,7,8,8aα-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamine
- Apramicina
- Apramycin
- Apramycine
- Apramycinum
- Nebramycin II
- External IDs
- EL-857
Pharmacology
- Indication
For the treatment of bacterial infections in animals.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria.
Target Actions Organism U16S ribosomal RNA Not Available Enteric bacteria and other eubacteria - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Apramycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac The risk or severity of nephrotoxicity can be increased when Apramycin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Apramycin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Apramycin is combined with Acenocoumarol. Acetaminophen Apramycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Apramycin sulfate 8UYL6NAZ3Q 65710-07-8 Not applicable
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminocyclitol glycosides
- Alternative Parents
- Hexoses / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / 1,3-aminoalcohols / 1,2-aminoalcohols / Oxacyclic compounds / Dialkylamines / Acetals show 4 more
- Substituents
- 1,2-aminoalcohol / 1,3-aminoalcohol / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Amine / Amino cyclitol glycoside / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives show 17 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- organic heterobicyclic compound, aminoglycoside, 2-deoxystreptamine derivative (CHEBI:2790)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 388K3TR36Z
- CAS number
- 37321-09-8
- InChI Key
- XZNUGFQTQHRASN-XQENGBIVSA-N
- InChI
- InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
- IUPAC Name
- (2R,3R,4S,5S,6S)-2-{[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
- SMILES
- CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O
References
- Synthesis Reference
Koji Tomita, Hiroshi Tsukiura, Hiroshi Kawaguchi, "Fermentation process for producing apramycin and nebramycin factor V'." U.S. Patent US4032404, issued December, 1974.
US4032404- General References
- Hermann T, Tereshko V, Skripkin E, Patel DJ: Apramycin recognition by the human ribosomal decoding site. Blood Cells Mol Dis. 2007 May-Jun;38(3):193-8. Epub 2007 Jan 29. [Article]
- Kondo J, Francois B, Urzhumtsev A, Westhof E: Crystal structure of the Homo sapiens cytoplasmic ribosomal decoding site complexed with apramycin. Angew Chem Int Ed Engl. 2006 May 12;45(20):3310-4. [Article]
- Han Q, Zhao Q, Fish S, Simonsen KB, Vourloumis D, Froelich JM, Wall D, Hermann T: Molecular recognition by glycoside pseudo base pairs and triples in an apramycin-RNA complex. Angew Chem Int Ed Engl. 2005 Apr 29;44(18):2694-700. [Article]
- External Links
- PDB Entries
- 1yrj / 2g5k / 2m4q / 2oe5 / 2oe8 / 4aqy / 4k31 / 6mn4 / 7jm2 / 7kes … show 10 more
- MSDS
- Download (40.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Basic Science Healthy Volunteers (HV) 1 1 Recruiting Treatment Bacterial Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder Oral Powder, for solution Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source pKa 8.5 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 53.3 mg/mL ALOGPS logP -2.8 ALOGPS logP -6.5 Chemaxon logS -1 ALOGPS pKa (Strongest Acidic) 12.29 Chemaxon pKa (Strongest Basic) 9.53 Chemaxon Physiological Charge 5 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 11 Chemaxon Polar Surface Area 283.64 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 120.91 m3·mol-1 Chemaxon Polarizability 54.46 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8007 Blood Brain Barrier - 0.9898 Caco-2 permeable - 0.7556 P-glycoprotein substrate Substrate 0.568 P-glycoprotein inhibitor I Non-inhibitor 0.8164 P-glycoprotein inhibitor II Non-inhibitor 0.9619 Renal organic cation transporter Non-inhibitor 0.885 CYP450 2C9 substrate Non-substrate 0.7737 CYP450 2D6 substrate Non-substrate 0.8285 CYP450 3A4 substrate Non-substrate 0.544 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9196 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9234 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8708 Ames test AMES toxic 0.5193 Carcinogenicity Non-carcinogens 0.9671 Biodegradation Not ready biodegradable 0.9023 Rat acute toxicity 2.2488 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9812 hERG inhibition (predictor II) Non-inhibitor 0.8385
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.1840904 predictedDarkChem Lite v0.1.0 [M-H]- 219.8899 predictedDeepCCS 1.0 (2019) [M+H]+ 229.4659904 predictedDarkChem Lite v0.1.0 [M+H]+ 221.73714 predictedDeepCCS 1.0 (2019) [M+Na]+ 229.6324904 predictedDarkChem Lite v0.1.0 [M+Na]+ 227.94258 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Unknown
References
- Woodcock J, Moazed D, Cannon M, Davies J, Noller HF: Interaction of antibiotics with A- and P-site-specific bases in 16S ribosomal RNA. EMBO J. 1991 Oct;10(10):3099-103. [Article]
- Kondo J, Francois B, Urzhumtsev A, Westhof E: Crystallographic studies of Homo sapiens ribosomal decoding A site complexed with aminoglycosides. Nucleic Acids Symp Ser (Oxf). 2005;(49):253-4. [Article]
Drug created at September 11, 2007 17:49 / Updated at June 12, 2021 10:53