Spectinomycin (HCID 15541)

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

SpectinomycinEspectinomicina1695-77-8TogamycinAntibiotic 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
EC Number: 216-911-3、606-950-8
Nikkaji: J7.562K

Properties

Computed structural properties

XLogP: -3.1
Topological polar surface area: 130 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 9
Rotatable bonds: 2
Heavy atoms: 23
Formal charge: 0
Complexity: 478

Experimental & physicochemical properties

LogP · 2 items

-2.3

Solubility · 2 items

Easily soluble in cold water

1.50e+02 g/L

Physical DescriptionSolid

Dissociation Constants6.95

Collision Cross Section · 2 items

176.2 Å² [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]；183.5 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

175.51 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；171.79 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；166.15 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；171.31 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 185 °C · 185 °C (decomp)
Boiling point: 583.1 · 583.1±50.0 °C(Predicted)
alpha: 25 · D25 -20° (water)
Density: 1.43 · 1.43±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 2 O, · DMSO/H2O, 1:1: soluble 100mg/mL
form: solution
pka: 1 · pKa1 6.95, pKa2 8.70(at 25℃)
color: colorless
biological source: Streptomyces sp.
FDA 21 CFR: 556.6 · 556.600
FDA UNII: 93 AKI1U6QF · 93AKI1U6QF
ATC code: 1 XX04 · J01XX04
EPA Substance Registry System: Spectinomycin (1695-77-8)
UNSPSC Code: 51281602 · 51281602
NACRES: 85 · NA.85
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
WGK Germany: 2 · WGK 2
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

GHS classification

GHS Classification · 6 items

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]；H319 (92.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (92.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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.；Reported as not meeting GHS hazard criteria per 3 of 54 reports by companies.；There are 4 notifications provided by 51 of 54 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

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 · 2 items

Skin Irrit. 2 (90.7%)；Eye Irrit. 2 (92.6%)；STOT SE 3 (92.6%)

Not Classified

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Regulatory 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.

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: WGK 2
Storage Class: 10 - Combustible liquids

Chemistry & industry

Pharmacology

ATC Code · 3 items

J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01X - Other antibacterials；J01XX - Other antibacterials；J01XX04 - Spectinomycin

QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01X - Other antibacterials；QJ01XX - Other antibacterials；QJ01XX04 - Spectinomycin

J01XX04

Protein BindingNot significant

Pharmacodynamics · 1 item

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.

Uses & manufacturing

Use Classification · 6 items

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes

Applications · 4 items

DescriptionAn unusual aminoglycoside antibiotic, spectinomycin is produced by fermentation of Streptomyces spectabil is and differs substantially in its clinical properties from the others. The diaminoinositol unit (spectinamine) contains two mono-N-methyl groups, and the hydroxyl between them has a stereochemistry opposite to that in streptomycin. The glycosidically attached sugar also is unusual in that it contains three consecutive carbonyl groups, either overt or masked, and is fused by two adjacent linkages to spectinamine to produce an unusual, fused, three-ring structure.

UsesAnalogous to streptomycin, spectinomycin binds with ribosomal 30 S subunits of microorganisms and inhibits protein synthesis; however, incorrect reading of the genetic code does not take place. Despite the broad spectrum of activity, spectinomycin is used only for gonococci infections. Other Gram-negative bacteria begin to display resistance during treatment. It is effective with respect to most strains of gonococci, as well as a number of other Gram-negative microorganisms.It is used for treating severe gonorrheal urethritis and proctitis in men, and severe gonorrheal proctitis in women, which is caused by strains of gonococci that are sensitive to the drug. Synonyms of this drug are actinospectocin, spectam, togamicin, and others.

UsesSpectinomycin finds principal application in the treatment of gonorrhea. It should be noted that the antibiotic resistance among N. gonorrhoeae has caused a number of therapeutic problems. It has been found that only by escalating the antibiotic doses and using probenecid to retard the excretion of penicillin and ampicillin (the drugs of choice) has the continued effective use of penicillin, ampicillin, and tetracycline been possible. Even with modifications in the therapy, from 3 to 8% of cases fail to respond to the usual regimens for uncomplicated gonorrhea. Thus, the treatment of uncomplicated gonorrhea that fails to respond to the usual regimen is spectinomycin therapy.

UsesSpectinomycin is an aminocyclitol antibiotic. It is used as a medicine in humans to treat Neisseria gonorrhoeae and is also used in veterinary medicine, especially in poultry, pigs and cattle. Cases of dermatitis have been reported in veterinary practice.

Upstream & downstream products

Upstream raw materials

Carbamic acid, [(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-decahydro-4a,7,9-trihydroxy-2-methyl-4-oxo-2H-pyrano[2,3-b][1,4]benzodioxin-6,8-diyl]bis[N-methyl-, C,C'-bis(phenylmethyl) ester

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]

山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]

Shaanxi Cuikang Pharmaceutical Technology Co., Ltd+86-13119157289 · [email protected]

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes

DefinitionChEBI: An organic heterotricyclic 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.