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

Structure Search

SMILES

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=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

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

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16	Binding Agent 964	Streptococcal Infections

Conditions

Condition	Modality	Targets	Highest Phase	Product
Staphylococcal Infections 41	Primary	70S ribosome	Approved 7888	LINCOCIN
Streptococcal Infections 12	Primary	70S ribosome	Approved 7888	LINCOCIN
Pneumococcal Infections 9	Primary	70S ribosome	Approved 7888	LINCOCIN

PubMed

Title	Date	PubMed
Lincomycin in larger doses.	1968 Nov 25	5754933
[Treatment of surgical infections with lincomycin and 7-chlor-lincomycin].	1970 Jan	4909441
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
Lincomycin-curare interaction.	1975 Jan-Feb	1167742
The spectrum of colitis associated with lincomycin and clindamycin therapy.	1975 May	1127264
[Letter: Cardiac arrest following the rapid intravenous injection of lincomycin].	1975 May 24	1215171
[Cardiorespiratory arrest due to intraperitoneal absorption of Lincocin].	1979 Mar	551330
Further observations in lincomycin-induced cholelithiasis in guinea-pigs.	1980 Jun	7431143
Acute interstitial nephritis associated with gentamicin and lincomycin therapy.	1980 Jun	7413550
Clindamycin-induced cardiac arrest.	1982 Jun	7089634
Sideroblastic anaemia associated with lincomycin therapy.	1983 Dec	6657545
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991 Nov-Dec	1818183
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.	1997 May	9145860
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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 `Mon Oct 21 19:48:28 UTC 2019` Edited by `admin` on `Mon Oct 21 19:48:28 UTC 2019`
Record UNII	BOD072YW0F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINCOMYCIN

Official Name

English

LINCOMYCIN [MI]

Common Name

English

D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE, METHYL 6,8-DIDEOXY-6-(((1-METHYL-4-PROPYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-, (2S-TRANS)-

Common Name

English

LINCOLNENSIN

Common Name

English

CLINDAMYCIN HYDROCHLORIDE IMPURITY A [IP]

Common Name

English

U-10,149

Code

English

U-10149

Code

English

LINCOMYCIN [GREEN BOOK]

Common Name

English

LINCOMYCIN [MART.]

Common Name

English

LINCOMYCIN [VANDF]

Common Name

English

LINCOMYCIN [USAN]

Common Name

English

METHYL 6,8-DIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYLPYRROLIDIN-2-YL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE

Systematic Name

English

LINCOMYCIN [INN]

Common Name

English

LINCOMYCIN [HSDB]

Common Name

English

LINCOMYCIN [WHO-DD]

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

Common Name

English

METHYL 6,8-DIDEOXY-6-TRANS-(1-METHYL-4-PROPYL-L-2-PYRROLIDINECARBOXAMIDO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01FF02