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Substance Name: Lincomycin [USAN:INN:BAN]
RN: 154-21-2
UNII: BOD072YW0F
InChIKey: OJMMVQQUTAEWLP-KIDUDLJLSA-N

Note

  • An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Molecular Formula

  • C18-H34-N2-O6-S

Molecular Weight

  • 406.5406
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors

Names and Synonyms

Name of Substance

  • Lincomycin
  • Lincomycin [USAN:INN:BAN]

MeSH Heading

  • Lincomycin

Synonyms

  • BRN 0707677
  • Cillimycin
  • D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, (2S-trans)-
  • D-erythro-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, trans-alpha-
  • EINECS 205-824-6
  • HSDB 3109
  • Jiemycin
  • Lincolcina
  • Lincolnensin
  • Lincomicina
  • Lincomicina [INN-Spanish]
  • Lincomycin
  • Lincomycin A
  • Lincomycine
  • Lincomycine [French]
  • Lincomycine [INN-French]
  • Lincomycinum
  • Lincomycinum [INN-Latin]
  • Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octopyranoside (alpha-form)
  • Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside
  • NSC-70731
  • U 10,149A
  • U-10,149
  • UNII-BOD072YW0F

Systematic Names

  • D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-((((2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-
  • D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, (2S-trans)-
  • Lincomycin

Registry Numbers

CAS Registry Number

  • 154-21-2

FDA UNII

  • BOD072YW0F

Other Registry Numbers

  • 12768-69-3
  • 16977-76-7

Related Registry Numbers

  • 7179-49-9 (mono-hydrochloride, hemi.hydrate)
  • 859-18-7 (mono-hydrochloride)

System Generated Number

  • 0000154212

Structure Descriptors

InChI

1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1

InChIKey

OJMMVQQUTAEWLP-KIDUDLJLSA-N

Smiles

CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 1800mg/kg (1800mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BLOOD: OTHER CHANGES
Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990.
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antimicrobial Agents and Chemotherapy Vol. -,
mouse LD50 intravenous 214mg/kg (214mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 7, Pg. 913, 1965.
mouse LD50 oral 13900mg/kg (13900mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BLOOD: OTHER CHANGES
Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990.
rabbit LDLo intramuscular 200ug/kg (0.2mg/kg)   Recueil de Medecine Veterinaire. Vol. 156, Pg. 915, 1980.
rat LD50 intraperitoneal 1900mg/kg (1900mg/kg) BLOOD: OTHER CHANGES

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(2), Pg. 40, 1990.
rat LD50 oral 1gm/kg (1000mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 186, 1978.
rat LD50 subcutaneous 9778mg/kg (9778mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.56 (none)   EXP
Water Solubility 927 mg/L 25 EST
Vapor Pressure 1.34E-17 mm Hg 25 EST
Henry's Law Constant 3.00E-23 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.84E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.