lincomycin

Also known as Frademicina, Lincocin, Cillimycin, U-10149, Lincomycine, LCM, Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside

Lincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. It was released for medical use in September 1964.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 408578167
Drug.IUPAC_name: (2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
Drug.image: Lincomycin.svg
Drug.image_class: skin-invert-image
Drug.image2: Lincomycin molecule ball.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.alt2: Ball-and-stick model of lincomycin
Drug.tradename: Biocine, Lincocin
Drug.MedlinePlus: a609005
Drug.routes_of_administration: IM/IV
Drug.ATC_prefix: J01
Drug.ATC_suffix: FF02
Drug.legal_AU: S4
Drug.legal_US: Rx-only
Drug.bioavailability: N/A

via Wikipedia infobox

Chemical data

Formula: C18H34N2O6S
Molecular weight: 406.5 g/mol
IUPAC name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O
InChIKey: OJMMVQQUTAEWLP-KIDUDLJLSA-N
XLogP: 0.2
Polar surface area: 148 Å²
H-bond donors: 5
H-bond acceptors: 8
Formal charge: 0

via PubChem

Research

10,119 papers

Lincomycin.Pediatric clinics of North America · 1968
Lincomycin and clindamycin.Antibiotics and chemotherapy · 1978
Lincomycin, clindamycin and their applications.Applied microbiology and biotechnology · 2004
[Antibiotic lincomycin].Antibiotiki · 1968
Lincomycin: fact, fancy, and future.The Medical clinics of North America · 1970

via PubMed

Wikidata facts

Mass: 406.214

Show 5 more facts

Commons category: Lincomycin
chemical formula: C₁₈H₃₄N₂O₆S
canonical SMILES: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O
isomeric SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O
World Health Organisation international non-proprietary name: lincomycin

Sources (7)

via Wikidata · CC0

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