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Identification
NameSpectinomycin
Accession NumberDB00919  (APRD01232)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.

Structure
Thumb
Synonyms
Actinospectacina
Espectinomicina
SCM
Spectinomicina
Spectinomycine
Spectinomycinum
External Identifiers
  • Antibiotic 2233wp
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Trobicin Inj 400mg/mlpowder for solution400 mgintramuscularThe Upjohn Company Of Canada1972-12-311997-08-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActinospectacinNot Available
SpectamNot Available
TogamycinNot Available
TrobicinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Spectinomycin dihydrochloride pentahydrate
ThumbNot applicableDBSALT001630
Spectinomycin hydrochloride
Thumb
  • InChI Key: BIPVCOUVVAMJMZ-MTTMTQIXSA-N
  • Monoisotopic Mass: 368.135028871
  • Average Mass: 368.811
DBSALT000380
Spectinomycin hydrochloride pentahydrate
ThumbNot applicableDBSALT001637
Spectinomycin sulfate tetrahydrate
ThumbNot applicableDBSALT001629
Categories
UNII93AKI1U6QF
CAS number1695-77-8
WeightAverage: 332.3496
Monoisotopic: 332.158351132
Chemical FormulaC14H24N2O7
InChI KeyInChIKey=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
IUPAC Name
(1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0³,⁸]tetradecan-7-one
SMILES
[H][C@@]12O[[email protected]](C)CC(=O)[C@]1(O)O[C@]1([H])[C@@H](NC)[C@@H](O)[C@@H](NC)[[email protected]](O)[C@@]1([H])O2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexylamines. These are organic compounds containing a cyclohexylamine moiety, which consist of a cyclohexane ring attached to an amine group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassCyclohexylamines
Sub ClassNot Available
Direct ParentCyclohexylamines
Alternative Parents
Substituents
  • Cyclohexylamine
  • Oxane
  • Para-dioxane
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Ketone
  • Hemiacetal
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the treatment of acute gonorrheal urethritis and proctitis in the male and acute gonorrheal cervicitis and proctitis in the female when due to susceptible strains of Neisseria gonorrhoeae.
PharmacodynamicsSpectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as Streptomyces spectabilis. In vitro studies have shown spectinomycin to be active against most strains of Neisseria gonorrhoeae (minimum inhibitory concentration <7.5 to 20 mcg/mL). Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure.
Mechanism of actionSpectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action.
Related Articles
AbsorptionRapidly and almost completely absorbed after intramuscular injection.
Volume of distributionNot Available
Protein bindingNot significant
MetabolismNot Available
Route of eliminationNot Available
Half life1 to 3 hours in patients with normal renal function and 10 to 30 hours in patients with impaired renal function with a creatinine clearance < 20 mL per minute.
ClearanceNot Available
ToxicityAcute oral toxicity (LD50): >5000 mg/kg [Rat]. Information on overdosage in humans is not available.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Spectinomycin Action PathwayDrug actionSMP00258
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7118
Blood Brain Barrier-0.9892
Caco-2 permeable-0.6803
P-glycoprotein substrateNon-substrate0.526
P-glycoprotein inhibitor INon-inhibitor0.6468
P-glycoprotein inhibitor IINon-inhibitor0.9228
Renal organic cation transporterNon-inhibitor0.9646
CYP450 2C9 substrateNon-substrate0.7711
CYP450 2D6 substrateNon-substrate0.8496
CYP450 3A4 substrateNon-substrate0.5056
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9182
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9254
Ames testNon AMES toxic0.7167
CarcinogenicityNon-carcinogens0.9602
BiodegradationNot ready biodegradable0.983
Rat acute toxicity1.8538 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.996
hERG inhibition (predictor II)Non-inhibitor0.9493
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Powder for solutionintramuscular400 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityEasily soluble in cold waterNot Available
logP-2.3Not Available
pKa6.95MERCK INDEX (1996); pKa1
Predicted Properties
PropertyValueSource
Water Solubility150.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.4ChemAxon
logS-0.35ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area129.51 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.44 m3·mol-1ChemAxon
Polarizability33.39 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

David R. White, “Intermediate compounds in the preparation of spectinomycin.” U.S. Patent US4344882, issued August, 1966.

US4344882
General ReferencesNot Available
External Links
ATC CodesJ01XX04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (24.8 KB)
Interactions
Drug Interactions
Drug
Alendronic acidSpectinomycin may increase the activities of Alendronate.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Spectinomycin.
Atracurium besylateSpectinomycin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Spectinomycin.
Botulinum Toxin Type ASpectinomycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Spectinomycin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Spectinomycin.
CarboplatinSpectinomycin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Spectinomycin.
CefdinirCefdinir may increase the nephrotoxic activities of Spectinomycin.
CefiximeCefixime may increase the nephrotoxic activities of Spectinomycin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Spectinomycin.
CefotetanCefotetan may increase the nephrotoxic activities of Spectinomycin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Spectinomycin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Spectinomycin.
CefprozilCefprozil may increase the nephrotoxic activities of Spectinomycin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Spectinomycin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Spectinomycin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Spectinomycin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Spectinomycin.
CelecoxibCelecoxib may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateSpectinomycin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Spectinomycin.
ClavulanateThe serum concentration of Spectinomycin can be decreased when it is combined with Clavulanate.
ClodronateSpectinomycin may increase the activities of Clodronate.
ColistimethateSpectinomycin may increase the nephrotoxic activities of Colistimethate.
ColistinSpectinomycin may increase the nephrotoxic activities of Colistin.
CyclosporineSpectinomycin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
DiflunisalDiflunisal may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Spectinomycin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Spectinomycin.
EtodolacEtodolac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Spectinomycin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Spectinomycin.
IbandronateSpectinomycin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Spectinomycin.
MecamylamineSpectinomycin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
NabumetoneNabumetone may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
NaproxenNaproxen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
OxaprozinOxaprozin may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateSpectinomycin may increase the activities of Pamidronate.
PancuroniumSpectinomycin may increase the activities of Pancuronium.
PiperacillinThe serum concentration of Spectinomycin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateSpectinomycin may increase the activities of Risedronate.
RocuroniumSpectinomycin may increase the activities of Rocuronium.
SuccinylcholineSpectinomycin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Spectinomycin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Spectinomycin can be decreased when it is combined with Ticarcillin.
TiludronateSpectinomycin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Spectinomycin.
VancomycinVancomycin may increase the nephrotoxic activities of Spectinomycin.
VecuroniumSpectinomycin may increase the activities of Vecuronium.
Zoledronic acidSpectinomycin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
Molecular Weight:
13736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Yamagata H, Dombou M, Sato T, Mizushima S, Uchida H: Deletion mapping and heterogenote analysis of a mutation responsible for osmosis-sensitive growth, spectinomycin resistance, and alteration of cytoplasmic membrane in Escherichia coli. J Bacteriol. 1980 Aug;143(2):661-7. [PubMed:6451613 ]
  4. Gordeev VK, Turkov MI: [Functioning of amino acid operons in Escherichia coli strains with an altered transcription and translation apparatus. II. The effect of mutations in genes coding ribosomal protein S5 and translation elongation factor G on the functioning of the ilv operon]. Genetika. 1983;19(2):217-20. [PubMed:6339322 ]
  5. Eisenstein BI, Beachey EH, Ofek I: Influence of sublethal concentrations of antibiotics on the expression of the mannose-specific ligand of Escherichia coli. Infect Immun. 1980 Apr;28(1):154-9. [PubMed:6103875 ]
  6. Carter AP, Clemons WM, Brodersen DE, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V: Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature. 2000 Sep 21;407(6802):340-8. [PubMed:11014183 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23