Spectinomycin

Basic Info

Common NameSpectinomycin(F05712)
2D Structure
FRCD IDF05712
CAS Number1695-77-8
PubChem CID15541
FormulaC14H24N2O7
IUPAC Name

None

InChI Key

UNFWWIHTNXNPBV-WXKVUWSESA-N

InChI

InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1

Canonical SMILES

CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)NC)O)NC)O)O

Isomeric SMILES

C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O

Synonyms
        
            Antibiotic 2233wp
        
            Spectinomycin
        
            Espectinomicina
        
            Togamycin
        
            actinospectacin
        
            Trobicin
        
            Spectam
        
            1695-77-8
        
            Spectinomycine
        
            Spectinomycinum
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDioxanes
Subclass1,4-dioxanes
Intermediate Tree NodesNot available
Direct Parent1,4-dioxanes
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsPara-dioxane - Oxane - Cyclic alcohol - 1,2-aminoalcohol - Secondary alcohol - Hemiacetal - Ketone - Acetal - Secondary aliphatic amine - Oxacycle - Secondary amine - Polyol - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Amine - Alcohol - Organopnictogen compound - Organic oxygen compound - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.

Properties

Property NameProperty Value
Molecular Weight332.353
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Complexity478
Monoisotopic Mass332.158
Exact Mass332.158
XLogP-3.1
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9892
Human Intestinal AbsorptionHIA-0.7118
Caco-2 PermeabilityCaco2-0.6803
P-glycoprotein SubstrateNon-substrate0.5260
P-glycoprotein InhibitorNon-inhibitor0.6468
Non-inhibitor0.9228
Renal Organic Cation TransporterNon-inhibitor0.9646
Distribution
Subcellular localizationMitochondria0.3675
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7711
CYP450 2D6 SubstrateNon-substrate0.8496
CYP450 3A4 SubstrateNon-substrate0.5056
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9182
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8434
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9254
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9960
Non-inhibitor0.9493
AMES ToxicityNon AMES toxic0.7167
CarcinogensNon-carcinogens0.9602
Fish ToxicityHigh FHMT0.5573
Tetrahymena Pyriformis ToxicityHigh TPT0.9499
Honey Bee ToxicityLow HBT0.5162
BiodegradationNot ready biodegradable0.9830
Acute Oral ToxicityIII0.7909
Carcinogenicity (Three-class)Non-required0.5741
Model Value Unit
Absorption
Aqueous solubility-2.9211LogS
Caco-2 Permeability0.0522LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8538LD50, mol/kg
Fish Toxicity1.6860pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3431pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle Of CattleUnited States0.25ppm
Kidney Of CattleUnited States4ppm
Edible Tissues Of TurkeysUnited States0.1ppm
Edible Tissues Of ChickensUnited States0.1ppm
Other Aquatic AnimalJapan0.3ppm
CrustaceansJapan0.3ppm
Shelled MolluscasJapan0.3ppm
Other FishJapan0.3ppm
PerciformesJapan0.3ppm
AnguilliformesJapan0.3ppm
SalmoniformesJapan0.3ppm
Other Poultry,EggsJapan2ppm
Other Poultry Animals,Edible OffalJapan0.6ppm
Chicken,Edible OffalJapan0.4ppm
Other Poultry Animals,KidneyJapan2ppm
Other Poultry Animals,LiverJapan0.7ppm
Other Poultry Animals,FatJapan0.3ppm
Other Poultry Animals,MuscleJapan0.5ppm
Other Terrestrial Mammals,Edible OffalJapan1ppm
Pig,Edible OffalJapan1ppm

References

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Antibiotic susceptibilities of livestock isolates of leptospira.Int J Antimicrob Agents2018 May29305960
A Novel aadA Aminoglycoside Resistance Gene in Bovine and Porcine Pathogens.mSphere2018 Feb 2829507894
Antibiotic effects on seed germination and root development of tomato (Solanumlycopersicum L.).Ecotoxicol Environ Saf2018 Feb29035755
Antimicrobial resistance trends in Escherichia coli isolated from diseasedfood-producing animals in France: A 14-year period time-series study.Zoonoses Public Health2018 Feb29110404
Occurrence of Salmonella genomic island 1 (SGI1) in two African Proteus mirabilis strains isolated from diseased chicken flocks.Infect Genet Evol2018 Apr 829641984
Poultry hatcheries as potential reservoirs for antimicrobial-resistantEscherichia coli: A risk to public health and food safety.Sci Rep2018 Apr 1129643424
Antimicrobial resistance and resistance genes in Salmonella strains isolated frombroiler chickens along the slaughtering process in China.Int J Food Microbiol2017 Oct 1628800411
Determinants of virulence and of resistance to ceftiofur, gentamicin, andspectinomycin in clinical Escherichia coli from broiler chickens in Québec,Canada.Vet Microbiol2017 May28619137
Isolation and characterization of Avibacterium paragallinarum with differentnicotinamide adenine dinucleotide requirements.Vet Microbiol2017 Jun28622864
First report in Africa of two clinical isolates of Proteus mirabilis carryingSalmonella genomic island (SGI1) variants, SGI1-PmABB and SGI1-W.Infect Genet Evol2017 Jul28359833
Mutations Associated with Decreased Susceptibility to Seven AntimicrobialFamilies in Field and Laboratory-Derived Mycoplasma bovis Strains.Antimicrob Agents Chemother2017 Jan 2427895010
Antimicrobial resistance and class 1 integron-associated gene cassettes inSalmonella enterica serovar Typhimurium isolated from pigs at slaughter andabattoir environment.Vet Microbiol2016 Oct 1527142182
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Determination of aminoglycoside residues in milk and muscle based on a simple andfast extraction procedure followed by liquid chromatography coupled to tandemmass spectrometry and time of flight mass spectrometry.Talanta2016 Jul 127154646
Biological evaluation and molecular docking of some chromenyl-derivatives aspotential antimicrobial agents.Pak J Pharm Sci2016 Jan27005495
Importance of Translocon Subunit Tic56 for rRNA Processing and ChloroplastRibosome Assembly.Plant Physiol2016 Dec27733515
Antibiotic susceptibility profiles of Mycoplasma sp. 1220 strains isolated fromgeese in Hungary.BMC Vet Res2016 Aug 1927543140
Antibiotic and heavy-metal resistance of Vibrio parahaemolyticus isolated from fresh shrimps in Shanghai fish markets, China.Environ Sci Pollut Res Int2016 Aug27083906
Characterization of Antimicrobial Resistance in Salmonella enterica Isolated from Pork, Chicken Meat, and Humans in Northeastern Thailand.Foodborne Pathog Dis2015 Sep26204443