(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

• ChemBase ID: 1403
• Molecular Formular: C18H34N2O6S
• Molecular Mass: 406.53736
• Monoisotopic Mass: 406.21375782
• SMILES: S([C@H]1O[C@H]([C@H](NC(=O)C2N(C[C@@H](C2)CCC)C)[C@H](O)C)[C@H](O)[C@H](O)[C@H]1O)C
• Canonical SMILES: CCC[C@H]1CN(C(C1)C(=O)N[C@@H]([C@H]1O[C@H](SC)[C@@H]([C@H]([C@H]1O)O)O)[C@H](O)C)C
• InChI: 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-ISVUEQNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: cillimycin
• Brand Name: Lincocin; Lincocine; Lincolcina; Lincolnensin; Lincomix; Lincomix 20; Pura Ject 100; Mycivin; Lincorex
• Synonyms: LCM; Lincomycine; Lincomyocin; Lincomycin hydrochloride; Lincomycin

Database IDs

• CAS Number: 154-21-2
• PubChem SID: 160964863; 46506668
• PubChem CID: 656509

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.365502
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.7498562
• LogD (pH = 7.4): -0.99001026
• Log P: -0.3168542
• Molar Refractivity: 102.6663 cm^3
• Polarizability: 41.491238 Å^3
• Polar Surface Area: 122.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.5
• LOG S: -1.14
• Solubility (Water): 2.93e+01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.56 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01627

• Drug Groups: approved
• Description: An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections. [PubChem]
• Indication: Lincomycin is an antibiotic used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
• Pharmacology: Lincomycin is a lincosamide antibiotic that comes from the yeast Streptomyces lincolnensis. Lincomycin has been shown to be active in vitro against the following microorganisms: Aerobic gram-positive cocci: Streptococcus pyogenes and Viridans group streptococci; Aerobic gram-positive bacilli: Corynebacterium diphtheriae; Anaerobic gram-positive non-sporeforming bacilli: Propionibacterium acnes; Anaerobic gram-positive sporeforming bacilli: Clostridium tetani and Clostridium perfringens.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Presumed hepatic, however metabolites have not been fully characterized.
• Absorption: Rapidly absorbed from the gastrointestinal tract following oral administration. Approximately 20 to 30% absorbed orally in fasting state; absorption decreased when taken with food.
• Half Life: The biological half-life after intramuscular or intravenous administration is 5.4 ± 1.0 hours. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be twofold longer than in patients with normal hepatic function.
• Protein Binding: Protein binding decreases with increased plasma concentrations. Range, 28 to 86% (average, 70 to 75%). Albumin is not thought to be the primary binding component.
• Elimination: Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 3 percent). Tissue level studies indicate that bile is an important route of excretion.
• External Links: Wikipedia; RxList; Drugs.com