Lincomycin hydrochlorideProduct ingredient for Lincomycin

Show full entry for Lincomycin
Name
Lincomycin hydrochloride
Drug Entry
Lincomycin

Lincomycin is a lincosamide antibiotic first isolated from the soil bacterium Streptomyces lincolnensis in Lincoln, Nebraska.2 Clinical use of lincomycin has largely been superseded by its semisynthetic derivative clindamycin due to its higher efficacy and a wider range of susceptible organisms, though lincomycin remains in use.1,2

Lincomycin was approved by the FDA on December 29, 1964.10

See full entry for Lincomycin
Accession Number
DBSALT000109
Structure
Similar Structures
Synonyms
Anhydrous lincomycin hydrochloride / Lincolnensin hydrochloride / Lincomycin HCl
UNII
GCW8Y9936L
CAS Number
859-18-7
Weight
Average: 443.0
Monoisotopic: 442.1904357
Chemical Formula
C18H35ClN2O6S
InChI Key
POUMFISTNHIPTI-BOMBIWCESA-N
InChI
InChI=1S/C18H34N2O6S.ClH/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);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1
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 hydrochloride
SMILES
Cl.[H][C@]1(C[C@@H](CCC)CN1C)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O
PubChem Compound
21872023
ChemSpider
58258
ChEMBL
CHEMBL1201097
Wikipedia
Lincomycin
Predicted Properties
PropertyValueSource
Water Solubility29.3 mg/mLALOGPS
logP0.5ALOGPS
logP-0.32Chemaxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.37Chemaxon
pKa (Strongest Basic)7.97Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area122.49 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity102.67 m3·mol-1Chemaxon
Polarizability43.7 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon