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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.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

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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H34N2O6S
Molecular Weight 406.537
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LINCOCIN
Primary
LINCOCIN
Primary
LINCOCIN
PubMed

PubMed

TitleDatePubMed
Lincomycin in larger doses.
1968 Nov 25
[Treatment of surgical infections with lincomycin and 7-chlor-lincomycin].
1970 Jan
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973 Sep
Lincomycin-induced cardiac arrest: a case report and laboratory investigation.
1974 Jul-Aug
Lincomycin-curare interaction.
1975 Jan-Feb
The spectrum of colitis associated with lincomycin and clindamycin therapy.
1975 May
[Letter: Cardiac arrest following the rapid intravenous injection of lincomycin].
1975 May 24
[Cardiorespiratory arrest due to intraperitoneal absorption of Lincocin].
1979 Mar
Further observations in lincomycin-induced cholelithiasis in guinea-pigs.
1980 Jun
Acute interstitial nephritis associated with gentamicin and lincomycin therapy.
1980 Jun
Clindamycin-induced cardiac arrest.
1982 Jun
Sideroblastic anaemia associated with lincomycin therapy.
1983 Dec
Screening for new compounds with antiherpes activity.
1984 Oct
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

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: Intramuscular; Intravenous; Subconjunctival injection
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 Tue Oct 22 06:13:17 UTC 2019
Edited
by admin
on Tue Oct 22 06:13:17 UTC 2019
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
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 [WHO-DD]
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 Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
212-726-7
Created by admin on Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
PRIMARY
CAS
859-18-7
Created by admin on Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
PRIMARY
NCI_THESAURUS
C90876
Created by admin on Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
PRIMARY
MERCK INDEX
M6825
Created by admin on Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
PRIMARY
EPA CompTox
859-18-7
Created by admin on Tue Oct 22 06:13:17 UTC 2019 , Edited by admin on Tue Oct 22 06:13:17 UTC 2019
PRIMARY
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