LINCOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H34N2O6S
Molecular Weight	406.537
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@](NC(=O)[C@@H]1C[C@@H](CCC)CN1C)([C@@H](C)O)[C@@]2([H])O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

InChI

InChIKey=OJMMVQQUTAEWLP-KIDUDLJLSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H34N2O6S
Molecular Weight	406.537
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Lincomycin (LINCOCIN®) is an antibiotic produced by Streptomyces lincolnensis (Streptomycetaceae family). It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections. Lincomycin (LINCOCIN®) inhibits protein synthesis in susceptible bacteria by binding to the 50S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible microorganisms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16	Binding Agent 1,064

Conditions

Condition	Modality	Highest Phase	Product
Streptococcal infections 11	Curative	Approved 8,429	LINCOCIN
Pneumococcal infections 9	Curative	Approved 8,429	LINCOCIN
Staphylococcal infections 24	Curative	Approved 8,429	LINCOCIN

C_max

Value	Dose	Analyte	Population
11.6 μg/mL	600 mg single, intramuscular	LINCOMYCIN serum	Homo sapiens
15.9 μg/mL	600 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
12.3 μg/mL	20 mg/kg bw single, intramuscular	LINCOMYCIN plasma	Ovis aries

AUC

Value	Dose	Analyte	Population
125.8 μg × h/mL	1200 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
212.8 μg × h/mL	2400 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
72.5 μg × h/mL	600 mg single, intravenous	LINCOMYCIN serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
5.4 h	1200 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
6.4 h	2400 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
5.1 h	600 mg single, intravenous	LINCOMYCIN serum	Homo sapiens
5.4 h	600 mg single, intramuscular	LINCOMYCIN serum	Homo sapiens
5.4 h	600 mg single, intravenous	LINCOMYCIN serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
43%	600 mg single, intravenous		LINCOMYCIN serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
500 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91	Other AEs: Diarrhoea...
501 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91	Other AEs: Abdominal pain...
502 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91	Other AEs: Pharyngitis...
503 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91	Other AEs: Upper respiratory infection...
504 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91	Other AEs: Vomiting...

Showing 1 to 5 of 10 entries

Previous1 2Next

AEs

Show entries

AE	Significance	Dose	Population
Diarrhoea	9 patients	500 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91
Abdominal pain	4 patients	501 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91
Pharyngitis	3 patients	502 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91
Upper respiratory infection	2 patients	503 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91
Vomiting	1 patient	504 mg 2 times / day multiple, oral Recommended	unhealthy, 17.5 n = 91

Showing 1 to 5 of 10 entries

Previous1 2Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270

Drug as victim

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3,367	unlikely

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6472	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6472
MolPort	MolPort-002-507-379	https://www.molport.com/shop/molecule-link/MolPort-002-507-379
ZINC	ZINC000003982483	http://zinc15.docking.org/substances/ZINC000003982483
eMolecules	26423691	https://www.emolecules.com/cgi-bin/more?vid=26423691
eMolecules	31240769	https://www.emolecules.com/cgi-bin/more?vid=31240769

Showing 1 to 5 of 5 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973 Sep	4202339
Lincomycin-induced cardiac arrest: a case report and laboratory investigation.	1974 Jul-Aug	4858250
The spectrum of colitis associated with lincomycin and clindamycin therapy.	1975 May	1127264
Further observations in lincomycin-induced cholelithiasis in guinea-pigs.	1980 Jun	7431143
Acute interstitial nephritis associated with gentamicin and lincomycin therapy.	1980 Jun	7413550

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Patents

Sample Use Guides

In Vivo Use Guide

Intramuscular: Serious infections - 600 mg (2 mL) intramuscularly every 24 hours. More severe infections - 600 mg (2 mL) intramuscularly every 12 hours or more often. Intravenous: For serious infections doses of 600 mg (2 mL) to 1 gram are given every 8 to 12 hours. For more severe infections these doses may have to be increased. In life-threatening situations daily intravenous doses of as much as 8 grams have been given. Subconjunctival injection: 0.25 mL (75 mg) injected subconjunctivally will result in ocular fluid levels of antibacterial (lasting for at least 5 hours) with MICs sufficient for most susceptible pathogens.

Route of Administration: Other

In Vitro Use Guide

The MIC values for lincomycin were: 0.4-1.6 ug/ml (Staphylococcus aureus, 36 strains), 0.2->100 ug/ml (Staphylococcus epidermidis, 35 strains).