Spectinomycin
Basic information
- CAS
1695-77-8- Standard SMILES
CN[C@@H]1[C@H](O)[C@H](NC)[C@H]2O[C@@]3(O)C(=O)C[C@@H](C)O[C@H]3O[C@@H]2[C@H]1O- InChIKey
UNFWWIHTNXNPBV-WXKVUWSESA-N- Molecular formula
- C14H24N2O7
- Average molar mass
- 332.35 g/mol
- Monoisotopic mass
- 332.15835111
Overview
Spectinomycin is a pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis. It has a role as an antimicrobial agent, an antibacterial drug and a bacterial metabolite. It is a pyranobenzodioxin, a secondary alcohol, a cyclic ketone, a secondary amino compound, a cyclic acetal and a cyclic hemiketal. It is a conjugate base of a spectinomycin(1+) and a spectinomycin(2+).
Names & identifiers
- Preferred name
- Spectinomycin
- IUPAC
- (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
- English name
- Spectinomycin
- Molecular formula
- C14H24N2O7
- Molecular weight
- 332.35
Names & synonyms
Spectinomycin1695-77-8EspectinomicinaTogamycinAntibiotic 2233wpSpectinomycineSpectinomycinumProspecAdspecM-141U 18409 E93AKI1U6QF
Show more names
trobicinspectamSpectacinmacromycinpectinomycin
SpectinomicinaCHX-3101U-18409ECHEBI:9215DTXSID90235924H-Pyrano(2,3-b)(1,4)benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-Pyrano(2,3-b)(1,4)benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4H-Pyrano[2,3-b][1,4]benzodioxin-4-one, decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-
Database identifiers
- CAS
1695-77-8、22189-32-8- PubChem CID
- 15541
- DTXSID
DTXSID9023592- ChEMBL
CHEMBL1167- ChEBI
CHEBI:9215- UNII
- 93AKI1U6QF
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 478
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP-2.3
Solubility
Easily soluble in cold water
1.50e+02 g/L
Human DrugsAccess group antibiotics
Animal Drugs
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Physical DescriptionSolid
Dissociation Constants6.95
Collision Cross Section
183.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
171.79 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5.6% (3 of 54) of reports.
Warning
H315 (90.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
Hazard information
Regulatory InformationSpectinomycin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryAllergic contact dermatitis reported in veterinarian workers; [Kanerva, p. 1171-2]
Hazard Classes and Categories
Skin Irrit. 2 (90.7%)
Not Classified
Toxicology
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- WGK 2
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01XX04
Protein BindingNot significant
Pharmacodynamics
Spectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as S<i>treptomyces spectabilis</i>. In vitro studies have shown spectinomycin to be active against most strains of <i>Neisseria gonorrhoeae</i> (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.
Biological 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.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionRapidly and almost completely absorbed after intramuscular injection.
Cellular LocationsCytoplasm
Metabolite PathwaysSpectinomycin Action Pathway
Uses & manufacturing
Use Classification
Related reactions
9 records
Compound notes
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