U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H34N2O6S.ClH
Molecular Weight 442.998
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINCOMYCIN HYDROCHLORIDE ANHYDROUS

SMILES

Cl.[H][C@@]1(O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O)[C@H](NC(=O)[C@@H]2C[C@@H](CCC)CN2C)[C@@H](C)O

InChI

InChIKey=POUMFISTNHIPTI-BOMBIWCESA-N
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

HIDE SMILES / InChI

Molecular Formula C18H34N2O6S
Molecular Weight 406.537
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68008034 | https://www.drugbank.ca/drugs/DB01627

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

Curator's Comment: Although lincomycin appears to diffuse into cerebrospinal fluid (CSF), levels of lincomycin in the CSF appear inadequate for the treatment of meningitis.

Originator

Curator's Comment: Source: Mason, D. J., Dietz, A. and DeBoer, C.: Lincomycin, a new antibiotic. I. Discovery and biological properties. In: Antimicrobial agents and chemotherapy. Proceedings of 2nd Interscience Conference on Antimicrobial Agents and Chemotherapy. Chicago, Illinois, October 31-November 2, 1962, edited by J. C. Sylvester, American Society for Microbiology, Ann Arbour, Michigan, 1963, p. 554.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2363853
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LINCOCIN

Approved Use

Lincomycin Injection, USP is indicated in the treatment of serious infections due to susceptible strains of streptococci, pneumococci, and staphylococci. Its use should be reserved for penicillin-allergic patients or other patients for whom, in the judgment of the physician, a penicillin is inappropriate. Because of the risk of antibacterial associated pseudomembranous colitis, as described in the WARNING box, before selecting lincomycin the physician should consider the nature of the infection and the suitability of less toxic alternatives (eg, erythromycin). Indicated surgical procedures should be performed in conjunction with antibacterial therapy. The drug may be administered concomitantly with other antimicrobial agents when indicated. Lincomycin is not indicated in the treatment of minor bacterial infections or viral infections. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Lincomycin and other antibacterial drugs, Lincomycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

-1.58025597E11
Curative
LINCOCIN

Approved Use

Lincomycin Injection, USP is indicated in the treatment of serious infections due to susceptible strains of streptococci, pneumococci, and staphylococci. Its use should be reserved for penicillin-allergic patients or other patients for whom, in the judgment of the physician, a penicillin is inappropriate. Because of the risk of antibacterial associated pseudomembranous colitis, as described in the WARNING box, before selecting lincomycin the physician should consider the nature of the infection and the suitability of less toxic alternatives (eg, erythromycin). Indicated surgical procedures should be performed in conjunction with antibacterial therapy. The drug may be administered concomitantly with other antimicrobial agents when indicated. Lincomycin is not indicated in the treatment of minor bacterial infections or viral infections. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Lincomycin and other antibacterial drugs, Lincomycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

-1.58025597E11
Curative
LINCOCIN

Approved Use

Lincomycin Injection, USP is indicated in the treatment of serious infections due to susceptible strains of streptococci, pneumococci, and staphylococci. Its use should be reserved for penicillin-allergic patients or other patients for whom, in the judgment of the physician, a penicillin is inappropriate. Because of the risk of antibacterial associated pseudomembranous colitis, as described in the WARNING box, before selecting lincomycin the physician should consider the nature of the infection and the suitability of less toxic alternatives (eg, erythromycin). Indicated surgical procedures should be performed in conjunction with antibacterial therapy. The drug may be administered concomitantly with other antimicrobial agents when indicated. Lincomycin is not indicated in the treatment of minor bacterial infections or viral infections. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Lincomycin and other antibacterial drugs, Lincomycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

Launch Date

-1.58025597E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11.6 μg/mL
600 mg single, intramuscular
dose: 600 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
15.9 μg/mL
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
12.3 μg/mL
20 mg/kg bw single, intramuscular
dose: 20 mg/kg bw
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
LINCOMYCIN plasma
Ovis aries
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
125.8 μg × h/mL
1200 mg single, intravenous
dose: 1200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
212.8 μg × h/mL
2400 mg single, intravenous
dose: 2400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
72.5 μg × h/mL
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.4 h
1200 mg single, intravenous
dose: 1200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6.4 h
2400 mg single, intravenous
dose: 2400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5.1 h
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5.4 h
600 mg single, intramuscular
dose: 600 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
5.4 h
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
43%
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LINCOMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Diarrhoea...
501 mg 2 times / day multiple, oral
Recommended
Dose: 501 mg, 2 times / day
Route: oral
Route: multiple
Dose: 501 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Abdominal pain...
502 mg 2 times / day multiple, oral
Recommended
Dose: 502 mg, 2 times / day
Route: oral
Route: multiple
Dose: 502 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Pharyngitis...
503 mg 2 times / day multiple, oral
Recommended
Dose: 503 mg, 2 times / day
Route: oral
Route: multiple
Dose: 503 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Upper respiratory infection...
Other AEs:
Upper respiratory infection (2 patients)
Sources:
504 mg 2 times / day multiple, oral
Recommended
Dose: 504 mg, 2 times / day
Route: oral
Route: multiple
Dose: 504 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Vomiting...
505 mg 2 times / day multiple, oral
Recommended
Dose: 505 mg, 2 times / day
Route: oral
Route: multiple
Dose: 505 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Rhinitis...
506 mg 2 times / day multiple, oral
Recommended
Dose: 506 mg, 2 times / day
Route: oral
Route: multiple
Dose: 506 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Cough...
507 mg 2 times / day multiple, oral
Recommended
Dose: 507 mg, 2 times / day
Route: oral
Route: multiple
Dose: 507 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Other AEs: Asthenia...
2100 mg 4 times / day multiple, intravenous
Studied dose
Dose: 2100 mg, 4 times / day
Route: intravenous
Route: multiple
Dose: 2100 mg, 4 times / day
Sources:
healthy, 21-46
n = 10
Health Status: healthy
Age Group: 21-46
Sex: M
Population Size: 10
Sources:
Other AEs: Dizziness...
Other AEs:
Dizziness (1 patient)
Sources:
75 - 2400 mg 4 times / day multiple, intravenous|intramuscular (complex)
Recommended
Dose: 75 - 2400 mg, 4 times / day
Route: intravenous|intramuscular
Route: multiple
Dose: 75 - 2400 mg, 4 times / day
Sources:
unhealthy, children
n = 265
Health Status: unhealthy
Condition: infection
Age Group: children
Population Size: 265
Sources:
Other AEs: Diarrhoea...
Other AEs:
Diarrhoea (3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhoea 9 patients
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Abdominal pain 4 patients
501 mg 2 times / day multiple, oral
Recommended
Dose: 501 mg, 2 times / day
Route: oral
Route: multiple
Dose: 501 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Pharyngitis 3 patients
502 mg 2 times / day multiple, oral
Recommended
Dose: 502 mg, 2 times / day
Route: oral
Route: multiple
Dose: 502 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Upper respiratory infection 2 patients
503 mg 2 times / day multiple, oral
Recommended
Dose: 503 mg, 2 times / day
Route: oral
Route: multiple
Dose: 503 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Vomiting 1 patient
504 mg 2 times / day multiple, oral
Recommended
Dose: 504 mg, 2 times / day
Route: oral
Route: multiple
Dose: 504 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Rhinitis 1 patient
505 mg 2 times / day multiple, oral
Recommended
Dose: 505 mg, 2 times / day
Route: oral
Route: multiple
Dose: 505 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Cough 1 patient
506 mg 2 times / day multiple, oral
Recommended
Dose: 506 mg, 2 times / day
Route: oral
Route: multiple
Dose: 506 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Asthenia 1 patient
507 mg 2 times / day multiple, oral
Recommended
Dose: 507 mg, 2 times / day
Route: oral
Route: multiple
Dose: 507 mg, 2 times / day
Sources:
unhealthy, 17.5
n = 91
Health Status: unhealthy
Condition: acute streptococcal tonsilitis/pharyngitis
Age Group: 17.5
Sex: M+F
Population Size: 91
Sources:
Dizziness 1 patient
2100 mg 4 times / day multiple, intravenous
Studied dose
Dose: 2100 mg, 4 times / day
Route: intravenous
Route: multiple
Dose: 2100 mg, 4 times / day
Sources:
healthy, 21-46
n = 10
Health Status: healthy
Age Group: 21-46
Sex: M
Population Size: 10
Sources:
Diarrhoea 3%
75 - 2400 mg 4 times / day multiple, intravenous|intramuscular (complex)
Recommended
Dose: 75 - 2400 mg, 4 times / day
Route: intravenous|intramuscular
Route: multiple
Dose: 75 - 2400 mg, 4 times / day
Sources:
unhealthy, children
n = 265
Health Status: unhealthy
Condition: infection
Age Group: children
Population Size: 265
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
unlikely
PubMed

PubMed

TitleDatePubMed
Lincomycin in larger doses.
1968 Nov 25
Lincomycin-induced cardiac arrest: a case report and laboratory investigation.
1974 Jul-Aug
Lincomycin-curare interaction.
1975 Jan-Feb
Further observations in lincomycin-induced cholelithiasis in guinea-pigs.
1980 Jun
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.
1991 Nov-Dec
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993 Sep 24
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:55:34 UTC 2023
Edited
by admin
on Fri Dec 15 16:55:34 UTC 2023
Record UNII
GCW8Y9936L
Record Status Validated (UNII)
Record Version
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Name Type Language
LINCOMYCIN HYDROCHLORIDE ANHYDROUS
Common Name English
ANHYDROUS LINCOMYCIN HYDROCHLORIDE [MART.]
Common Name English
Lincomycin hydrochloride [WHO-DD]
Common Name English
METHYL 6,8-DIDEOXY-6-(1-METHYL-TRANS-4-PROPYL-L-2-PYRROLIDINECARBOXAMIDO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE MONOHYDROCHLORIDE
Common Name English
(2S-TRANS)-METHYL 6,8-DIDEOXY-6-(((1-METHYL-4-PROPYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE HYDROCHLORIDE
Common Name English
LINCOMYCIN HYDROCHLORIDE ANHDROUS [MI]
Common Name English
LINCOLNENSIN HYDROCHLORIDE
Common Name English
ANHYDROUS LINCOMYCIN HYDROCHLORIDE
MART.  
Common Name English
D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE, METHYL 6,8-DIDEOXY-6-(((1-METHYL-4-PROPYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-, MONOHYDROCHLORIDE, (2S-TRANS)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C82922
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
212-726-7
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
SMS_ID
100000092573
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
PUBCHEM
64710
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
CAS
859-18-7
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
FDA UNII
GCW8Y9936L
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
NCI_THESAURUS
C90876
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
MERCK INDEX
m6825
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID7047803
Created by admin on Fri Dec 15 16:55:35 UTC 2023 , Edited by admin on Fri Dec 15 16:55:35 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY