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
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
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68008034 | https://www.drugbank.ca/drugs/DB01627
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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14217764
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363853 Sources: https://www.drugbank.ca/drugs/DB01627 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | LINCOCIN Approved UseLincomycin 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 Date1964 |
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Curative | LINCOCIN Approved UseLincomycin 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 Date1964 |
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Curative | LINCOCIN Approved UseLincomycin 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 Date1964 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
72.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 |
|
125.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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 |
|
5.4 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
43% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3950061 |
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
Dose | Population | Adverse 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Diarrhoea... Other AEs: Diarrhoea (9 patients) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Abdominal pain... Other AEs: Abdominal pain (4 patients) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Pharyngitis... Other AEs: Pharyngitis (3 patients) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Vomiting... Other AEs: Vomiting (1 patient) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Rhinitis... Other AEs: Rhinitis (1 patient) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Cough... Other AEs: Cough (1 patient) Sources: |
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F Sources: |
Other AEs: Asthenia... Other AEs: Asthenia (1 patient) Sources: |
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 |
Other AEs: Dizziness... |
75 - 2400 mg 4 times / day multiple, intravenous|intramuscular Recommended Dose: 75 - 2400 mg, 4 times / day Route: intravenous|intramuscular Route: multiple Dose: 75 - 2400 mg, 4 times / day Sources: |
unhealthy, children |
Other AEs: Diarrhoea... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 Health Status: unhealthy Age Group: 17.5 Sex: M+F 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 |
Diarrhoea | 3% | 75 - 2400 mg 4 times / day multiple, intravenous|intramuscular Recommended Dose: 75 - 2400 mg, 4 times / day Route: intravenous|intramuscular Route: multiple Dose: 75 - 2400 mg, 4 times / day Sources: |
unhealthy, children |
PubMed
Title | Date | PubMed |
---|---|---|
Lincomycin in larger doses. | 1968 Nov 25 |
|
[Treatment of surgical infections with lincomycin and 7-chlor-lincomycin]. | 1970 Jan |
|
Lincomycin-induced cardiac arrest: a case report and laboratory investigation. | 1974 Jul-Aug |
|
The spectrum of colitis associated with lincomycin and clindamycin therapy. | 1975 May |
|
Clindamycin-induced cardiac arrest. | 1982 Jun |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/938025
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
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Mon Mar 31 17:37:05 GMT 2025
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on
Mon Mar 31 17:37:05 GMT 2025
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Record UNII |
BOD072YW0F
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QJ01FF02
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CFR |
21 CFR 556.360
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CFR |
21 CFR 520.1263C
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LIVERTOX |
559
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CFR |
21 CFR 558.325
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CFR |
21 CFR 520.1263A
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WHO-ATC |
J01FF02
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CFR |
21 CFR 522.1260
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WHO-VATC |
QJ01FF52
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WHO-VATC |
QJ51RF03
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CFR |
21 CFR 520.1265
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NCI_THESAURUS |
C82922
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CFR |
21 CFR 520.1263
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Code System | Code | Type | Description | ||
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BOD072YW0F
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PRIMARY | |||
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SUB08517MIG
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PRIMARY | |||
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1419
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PRIMARY | |||
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m6825
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PRIMARY | Merck Index | ||
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DB01627
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PRIMARY | |||
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1582
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PRIMARY | |||
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DTXSID3023215
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CHEMBL1447
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100000082335
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PRIMARY | |||
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205-824-6
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3000540
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PRIMARY | |||
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6398
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PRIMARY | RxNorm | ||
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LINCOMYCIN
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PRIMARY | |||
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154-21-2
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PRIMARY | |||
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C61811
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PRIMARY | |||
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6472
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PRIMARY | |||
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D008034
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PRIMARY | |||
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3109
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BOD072YW0F
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PRIMARY |
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SALT/SOLVATE -> PARENT | |||
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DERIVATIVE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |