Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H39N5O8.ClH |
Molecular Weight | 622.11 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12CC3=C(C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]4(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]4([H])C2)N(C)C
InChI
InChIKey=ATIINCUPZOADER-KXLOKULZSA-N
InChI=1S/C29H39N5O8.ClH/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36;/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35);1H/t12-,14-,21-,29-;/m0./s1
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 |
Molecular Formula | C29H39N5O8 |
Molecular Weight | 585.6487 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00560
https://en.wikipedia.org/wiki/Tigecycline
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00560
https://en.wikipedia.org/wiki/Tigecycline
Tigecycline (INN) is an antibiotic used to treat a number of bacterial infections. It is a first in class glycylcycline that is administered intravenously. For the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by Escherichia coli, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus agalactiae, Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Streptococcus pyogenes and Bacteroides fragilis. Complicated intra-abdominal infections caused by Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Klebsiella oxytoca, Klebsiella pneumoniae, Enterococcus faecalis (vancomycin-susceptible isolates only), Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Clostridium perfringens, and Peptostreptococcus micros. Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of minocycline. The substitution pattern is not present in any naturally occurring or semisynthetic tetracycline and imparts certain microbiologic properties to tigecycline. In general, tigecycline is considered bacteriostatic; however, TYGACIL has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila. In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterials.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/17012300
Curator's Comment: On average, the systemic exposure of tigecycline in bone, SF and CSF ranged from 11% to 41% of serum concentrations.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | TYGACIL Approved Useis a tetracycline-class antibacterial drug indicated in patients 18 years of age and older for: Complicated skin and skin structure infections; Complicated intra-abdominal infections; Community-acquired bacterial pneumonia; Limitations of Use: TYGACIL is not indicated for treatment of diabetic foot infection or hospital-acquired pneumonia, including ventilator-associated pneumonia Launch Date2006 |
|||
Curative | TYGACIL Approved Useis a tetracycline-class antibacterial drug indicated in patients 18 years of age and older for: Complicated skin and skin structure infections; Complicated intra-abdominal infections; Community-acquired bacterial pneumonia; Limitations of Use: TYGACIL is not indicated for treatment of diabetic foot infection or hospital-acquired pneumonia, including ventilator-associated pneumonia Launch Date2006 |
|||
Curative | TYGACIL Approved Useis a tetracycline-class antibacterial drug indicated in patients 18 years of age and older for: Complicated skin and skin structure infections; Complicated intra-abdominal infections; Community-acquired bacterial pneumonia; Limitations of Use: TYGACIL is not indicated for treatment of diabetic foot infection or hospital-acquired pneumonia, including ventilator-associated pneumonia Launch Date2006 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.63 μg/mL |
50 mg 2 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
TIGECYCLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.7 μg × h/mL |
50 mg 2 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
TIGECYCLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.64 mg*h/L Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01560143 |
100 mg single, intravenous dose: 100 mg route of administration: intravenous experiment type: single co-administered: |
TIGECYCLINE serum | Homo sapiens |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.4 h |
50 mg 2 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
TIGECYCLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11% |
50 mg 2 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
TIGECYCLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 2 times / day multiple, intravenous Highest studied dose Dose: 100 mg, 2 times / day Route: intravenous Route: multiple Dose: 100 mg, 2 times / day Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Disc. AE: Gastrointestinal disorder (NOS)... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (NOS) (50%) Sources: Page: p.223 |
300 mg single, intravenous Highest studied dose Dose: 300 mg Route: intravenous Route: single Dose: 300 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
DLT: Gastrointestinal disorder NOS... Dose limiting toxicities: Gastrointestinal disorder NOS Sources: Page: p.223 |
100 mg single, intravenous MTD Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Other AEs: Nausea, Vomiting... |
200 mg single, intravenous MTD Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Other AEs: Nausea, Vomiting... |
50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.10 |
unhealthy n = 3788 Health Status: unhealthy Condition: Complicated skin and skin structure infections Population Size: 3788 Sources: Page: p.10 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (1%) Sources: Page: p.10Vomiting (1%) |
50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Disc. AE: Anaphylaxis, Anaphylactoid reaction... AEs leading to discontinuation/dose reduction: Anaphylaxis Sources: Page: p.1Anaphylactoid reaction Hepatic dysfunction NOS Liver failure Pancreatitis (grade 5) Fetal damage Tooth discoloration Diarrhea, Clostridium difficile |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disorder (NOS) | 50% Disc. AE |
100 mg 2 times / day multiple, intravenous Highest studied dose Dose: 100 mg, 2 times / day Route: intravenous Route: multiple Dose: 100 mg, 2 times / day Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Gastrointestinal disorder NOS | DLT | 300 mg single, intravenous Highest studied dose Dose: 300 mg Route: intravenous Route: single Dose: 300 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Nausea | 50% | 100 mg single, intravenous MTD Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Vomiting | 50% | 100 mg single, intravenous MTD Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
Nausea | 200 mg single, intravenous MTD Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
|
Vomiting | 200 mg single, intravenous MTD Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: Page: p.223 |
healthy n = 6 Health Status: healthy Population Size: 6 Sources: Page: p.223 |
|
Nausea | 1% Disc. AE |
50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.10 |
unhealthy n = 3788 Health Status: unhealthy Condition: Complicated skin and skin structure infections Population Size: 3788 Sources: Page: p.10 |
Vomiting | 1% Disc. AE |
50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.10 |
unhealthy n = 3788 Health Status: unhealthy Condition: Complicated skin and skin structure infections Population Size: 3788 Sources: Page: p.10 |
Anaphylactoid reaction | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Anaphylaxis | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Diarrhea, Clostridium difficile | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Fetal damage | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Hepatic dysfunction NOS | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Liver failure | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Tooth discoloration | Disc. AE | 50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Pancreatitis | grade 5 Disc. AE |
50 mg 2 times / day multiple, intravenous Recommended Dose: 50 mg, 2 times / day Route: intravenous Route: multiple Dose: 50 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no [IC50 >100 uM] | |||
Page: 36.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 36.0 |
inconclusive |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 5, 22 |
Sample Use Guides
Initial dose of 100 mg, followed by 50 mg every 12 hours administered intravenously over approximately 30 to 60 minutes.
Severe hepatic impairment (Child Pugh C): Initial dose of 100 mg followed by 25 mg every 12 hours.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18596149
Among the tested gram-positive isolates, tigecycline was most active as reflected by MIC50/MIC90 values against S. pyogenes (0.03/0.03 μg/ml) and S. pneumoniae (0.015/0.03 μg/ml), followed by S. aureus (0.12/0.25 μg/ml) and E. faecalis (0.12/0.5 μg/ml)
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:19:27 GMT 2023
by
admin
on
Sat Dec 16 15:19:27 GMT 2023
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Record UNII |
7F4TZ17Y3R
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Record Status |
Validated (UNII)
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Record Version |
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-
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7F4TZ17Y3R
Created by
admin on Sat Dec 16 15:19:27 GMT 2023 , Edited by admin on Sat Dec 16 15:19:27 GMT 2023
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197654-04-9
Created by
admin on Sat Dec 16 15:19:27 GMT 2023 , Edited by admin on Sat Dec 16 15:19:27 GMT 2023
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