린코마이신

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

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.

In the Vinony graph

Vinony's link graph records 146 inbound references to 린코마이신, and connects out to neomycin, macrolides and lincosamides.

Vinony files it under Drugboxes which contain changes to verified fields, Drugboxes which contain changes to watched fields and Drugs developed by Pfizer.

Vinony links it to 28 Wikipedia language editions.

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

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1964
Admin. routes: oral, parenteral
Indications: osteomyelitis, bacterial disease, multiple sclerosis

via ChEMBL · EBI

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

Has part: carbon
Mass: 406.214
Has use: medication

Show 8 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
medical condition treated: pneumococcal infection
subject has role: protein synthesis inhibitor
legal status (medicine): boxed warning