spectinomycin

Also known as Antibiotic 2233WP, SCM, Actinospectacina, Espectinomicina, Spectinomicina, Spectinomycine, Spectinomycinum

Spectinomycin, sold under the tradename Trobicin among others, is an antibiotic useful for the treatment of gonorrhea infections. It is given by injection into a muscle.

Chemical data

Formula: C14H24N2O7
Molecular weight: 332.35 g/mol
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: 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
InChIKey: UNFWWIHTNXNPBV-WXKVUWSESA-N
XLogP: -3.1
Polar surface area: 130 Å²
H-bond donors: 5
H-bond acceptors: 9
Formal charge: 0

via PubChem

Research

3,036 papers

Spectinomycin.The Medical clinics of North America · 1982
Fed-batch bioproduction of spectinomycin.Advances in biochemical engineering/biotechnology · 1998
Spectinomycin-resistant Neisseria gonorrhoeae.JAMA · 1977
Chemistry of spectinomycin.The Japanese journal of antibiotics · 1979
Drugs five years later. Spectinomycin.Annals of internal medicine · 1976

via PubMed

Wikidata facts

Mass: 332.158

Show 5 more facts

chemical formula: C₁₄H₂₄N₂O₇
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
canonical SMILES: CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)NC)O)NC)O)O
World Health Organisation international non-proprietary name: spectinomycin
defined daily dose: 3

Sources (4)

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Article

7 sections

Contents

Medical uses
Side effects
Mechanism of action
Biosynthetic mechanism
Nature
History
References

Spectinomycin, sold under the tradename Trobicin among others, is an antibiotic useful for the treatment of gonorrhea infections. It is given by injection into a muscle.

Common side effects include pain at the area of injection, rash, nausea, fever, and trouble sleeping. Severe allergic reactions may occasionally occur. It is generally safe to use during pregnancy. It may be used by those who are allergic to penicillin or cephalosporins. It is in the aminocyclitol class of drugs and works by stopping the making of protein by certain bacteria.