Spectinomycin

Base Information

• Chemical Name: Spectinomycin
• CAS No.: 1695-77-8
• Molecular Formula: C14H24N2O7
• Molecular Weight: 332.354
• Hs Code.: 3003209000
• European Community (EC) Number: 244-554-3,216-911-3,606-950-8
• UNII: 93AKI1U6QF
• DSSTox Substance ID: DTXSID9023592
• Nikkaji Number: J7.562K
• Wikipedia: Spectinomycin
• Wikidata: Q416154
• NCI Thesaurus Code: C61951
• Metabolomics Workbench ID: 43186
• ChEMBL ID: CHEMBL1167
• Mol file: 1695-77-8.mol

Synonyms:Actinospectacin;Adspec;Ferkel Spectam;Kempi;Prospec;Salmosan T;Salmosan-T;Spectam;Spectam, Ferkel;Spectinomycin;Spectinomycin Dihydrochloride, Anhydrous;Spectinomycin Dihydrochloride, Pentahydrate;Spectinomycin Hydrochloride;Stanilo;Trobicin

Chemical Property of Spectinomycin

Chemical Property:

• Appearance/Colour: a white to pale buff crystalline dihydrochloride pentahydrate powder
• Vapor Pressure: 5.05E-16mmHg at 25°C
• Melting Point: 185ºC
• Boiling Point: 583.1 °C at 760 mmHg
• PKA: pKa1 6.95, pKa2 8.70(at 25℃)
• Flash Point: 306.4 °C
• PSA: 129.51000
• Density: 1.43 g/cm³
• LogP: -2.14380
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 332.15835111
• Heavy Atom Count: 23
• Complexity: 478

Purity/Quality:

99% ^*data from raw suppliers

Spectinomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• 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
• Description: An 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.
• Uses: Analogous 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. Spectinomycin 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. Spectinomycin 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.
• Therapeutic Function: Antibacterial
• Clinical Use: Gonorrhea in penicillin-allergic patients or due to penicillin-resistant strains (single-dose treatment)

Technology Process of Spectinomycin

There total 13 articles about Spectinomycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1,3-bis(N-benzyloxycarbonyl)-spectinomycin (56733-83-6) → spectinomycin (1695-77-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol; at 25 ℃; for 12h;

DOI:10.1002/anie.200500434

Reference yield:

2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin (866941-38-0) → spectinomycin (1695-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / K₂CO₃ / methanol / 0.17 h / 25 °C

2: 90 percent / hydrogen / Pd/C / propan-2-ol / 12 h / 25 °C

With hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; isopropyl alcohol;

DOI:10.1002/anie.200500434

Reference yield:

→ spectinomycin (1695-77-8)

Guidance literature:

upstream raw materials:

1,3-bis(N-benzyloxycarbonyl)-spectinomycin

2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin

(+)-spectinomycin dihydrochloride

N,N'-<(benzyloxy)carbonyl>spectinomycin

Downstream raw materials:

C₃₅H₄₂N₄O₁₁S

Refernces

• 1、 Hanessian,Roy. "Chemistry of spectinomycin: Its total synthesis, stereocontrolled rearrangement, and analogs". . p. 163 - 172. Retrieved 2007/10/02.