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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H39N5O8
Molecular Weight 585.6487
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIGECYCLINE

SMILES

[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=FPZLLRFZJZRHSY-HJYUBDRYSA-N
InChI=1S/C29H39N5O8/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)/t12-,14-,21-,29-/m0/s1

HIDE SMILES / InChI
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

Description
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

CNS Penetrant
2554
Curator's Comment: On average, the systemic exposure of tigecycline in bone, SF and CSF ranged from 11% to 41% of serum concentrations.

Originator

Wyeth
116
Curator's Comment: # Wyeth Pharmaceuticals

Approval Year

2005
131
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
TYGACIL

Approved Use

is 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 Date

2006
Curative
Approved
8429
TYGACIL

Approved Use

is 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 Date

2006
Curative
Approved
8429
TYGACIL

Approved Use

is 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 Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.63 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021821s026s031lbl.pdf
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

AUC

ValueDoseCo-administeredAnalytePopulation
4.7 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021821s026s031lbl.pdf
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

T1/2

ValueDoseCo-administeredAnalytePopulation
42.4 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021821s026s031lbl.pdf
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

Funbound

ValueDoseCo-administeredAnalytePopulation
11%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021821s026s031lbl.pdf
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Disc. AE: Gastrointestinal disorder (NOS)...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorder (NOS) (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
300 mg single, intravenous
Highest studied dose
Dose: 300 mg
Route: intravenous
Route: single
Dose: 300 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
DLT: Gastrointestinal disorder NOS...
Dose limiting toxicities:
Gastrointestinal disorder NOS
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
100 mg single, intravenous
MTD
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (50%)
Vomiting (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea
Vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.10
unhealthy
n = 3788
Health Status: unhealthy
Condition: Complicated skin and skin structure infections
Population Size: 3788
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.10
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (1%)
Vomiting (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.10
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
Disc. AE: Anaphylaxis, Anaphylactoid reaction...
AEs leading to
discontinuation/dose reduction:
Anaphylaxis
Anaphylactoid reaction
Hepatic dysfunction NOS
Liver failure
Pancreatitis (grade 5)
Fetal damage
Tooth discoloration
Diarrhea, Clostridium difficile
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Nausea 50%
100 mg single, intravenous
MTD
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Vomiting 50%
100 mg single, intravenous
MTD
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Nausea
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
Vomiting
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Page: p.223
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.10
unhealthy
n = 3788
Health Status: unhealthy
Condition: Complicated skin and skin structure infections
Population Size: 3788
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.10
unhealthy
n = 3788
Health Status: unhealthy
Condition: Complicated skin and skin structure infections
Population Size: 3788
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Complicated skin and skin structure infections|Complicated intra-abdominal infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1478

CYP2C8
911

CYP1A2
1524

P-gp
1461
P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >100 uM]
CYP2C19
1553
 no [IC50 >100 uM]
CYP2C8
965
 no [IC50 >100 uM]
CYP2C9
1819
 no [IC50 >100 uM]
CYP2D6
1891
 no [IC50 >100 uM]
CYP3A4
1925
 no [IC50 >100 uM]
P-gp
1650
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 inconclusive
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:149836
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:149836
ChemicalBook
CB6248215
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6248215
MolPort
MolPort-009-199-379
https://www.molport.com/shop/molecule-link/MolPort-009-199-379
Selleck Chemicals
Tigecycline
http://www.selleckchem.com/products/Tigecycline.html
ZINC
ZINC000014879972
http://zinc15.docking.org/substances/ZINC000014879972
eMolecules
6719081
https://www.emolecules.com/cgi-bin/more?vid=6719081
PubMed

PubMed

TitleDatePubMed
Disk diffusion susceptibility test development for the new glycylcycline, GAR-936.
1999 Nov
Antimicrobial activity and spectrum of the new glycylcycline, GAR-936 tested against 1,203 recent clinical bacterial isolates.
2000 Jan
Comparison of the in vitro activity of the glycylcycline tigecycline (formerly GAR-936) with those of tetracycline, minocycline, and doxycycline against isolates of nontuberculous mycobacteria.
2002 Oct
Tigecycline: first of a new class of antimicrobial agents.
2006 Aug
Tigecycline: a new glycylcycline antimicrobial agent.
2006 Jul 1
Non-susceptibility trends among staphylococci from bacteraemias in the UK and Ireland, 2001-06.
2008 Nov
Fluorocyclines. 1. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: a potent, broad spectrum antibacterial agent.
2012 Jan 26
Tigecycline prevents LPS-induced release of pro-inflammatory and apoptotic mediators in neuronal cells.
2013 Mar
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

08252946
2
20030166585
2
JP2007515411A
2
JP2009191083A
2
JP2010024252A
2

Sample Use Guides

In Vivo Use Guide
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
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 Sat Dec 16 15:55:53 GMT 2023
Edited
by admin
on Sat Dec 16 15:55:53 GMT 2023
Record UNII
70JE2N95KR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIGECYCLINE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
Tigecycline [WHO-DD]
Common Name English
TIGECYCLINE [USAN]
Common Name English
TIGECYCLINE [USP-RS]
Common Name English
TIGECYCLINE [USP MONOGRAPH]
Common Name English
tigecycline [INN]
Common Name English
TIGECYCLINE [VANDF]
Common Name English
TIGECYCLINE [EP MONOGRAPH]
Common Name English
(4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
Common Name English
2-NAPHTHACENECARBOXAMIDE, 4,7-BIS(DIMETHYLAMINO)-9-((((1,1-DIMETHYLETHYL)AMINO)ACETYL)AMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-, (4S,4AS,5AR,12AS)-
Common Name English
WAY-GAR-936
Code English
TIGECYCLINE [MI]
Common Name English
TYGACIL
Brand Name English
TIGECYCLINE [ORANGE BOOK]
Common Name English
TIGECYCLINE [JAN]
Common Name English
TIGECYCLINE [MART.]
Common Name English
TIGECYCLINE [EMA EPAR]
Common Name English
Classification Tree Code System Code
WHO-ATC J01AA12
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
NDF-RT N0000007948
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
NDF-RT N0000175938
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
WHO-VATC QJ01AA12
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
FDA ORPHAN DRUG 406313
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
NDF-RT N0000007948
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
EMA ASSESSMENT REPORTS TYGACIL (AUTHORIZED SOFT TISSUE INFECTIONS)
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
LIVERTOX NBK547888
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
NCI_THESAURUS C258
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
Code System Code Type Description
CAS
220620-09-7
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
MESH
C119092
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID2048581
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
LACTMED
Tigecycline
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
INN
8115
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
RS_ITEM_NUM
1667643
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL376140
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
MERCK INDEX
m10858
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY Merck Index
CHEBI
149836
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
DAILYMED
70JE2N95KR
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
CHEBI
142708
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
NCI_THESAURUS
C72865
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
FDA UNII
70JE2N95KR
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
DRUG BANK
DB00560
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
EVMPD
SUB16467MIG
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
RXCUI
384455
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY RxNorm
USAN
LL-84
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
WIKIPEDIA
TIGECYCLINE
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
DRUG CENTRAL
2661
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
HSDB
8172
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
SMS_ID
100000089539
Created by admin on Sat Dec 16 15:55:55 GMT 2023 , Edited by admin on Sat Dec 16 15:55:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of TIGECYCLINE, (4R)-
DEGRADENT -> PARENT
ESCHERICHIA COLI
TARGET ORGANISM->INHIBITOR
Structure of TIGECYCLINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of TIGECYCLINE
EXCRETED UNCHANGED
URINE
ENTEROCOCCUS FAECALIS
TARGET ORGANISM->INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
The in vitro plasma protein binding of tigecycline ranges from approximately 71% to 89% at concentrations observed in clinical studies (0.1 to 1.0 μg/mL).
KLEBSIELLA PNEUMONIAE
TARGET ORGANISM->INHIBITOR
METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
STREPTOCOCCUS PNEUMONIAE
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of 9-AMINOMINOCYCLINE
METABOLITE -> PARENT
Trace amount; demonstrated some antibacterial activity in vitro, their activities were generally less than that of tigecycline and were effective against a narrower range of infectious organisms (data on file at Wyeth Research)
MINOR
PLASMA; URINE
Structure of TIGECYCLINE GLUCURONIDE, (4R)-
METABOLITE -> PARENT
MINOR
FECAL; PLASMA
Structure of 9-(N-ACETYLAMINO)MINOCYCLINE
METABOLITE -> PARENT
Although both M5 and M6 demonstrated some antibac- terial activity in vitro, their activities were generally less than that of tigecycline and were effective against a narrower range of infectious organisms (data on file at Wyeth Research).
PLASMA; URINE
Structure of N-TERT-BUTYLGLYCINE
METABOLITE -> PARENT
MAJOR
FECAL; PLASMA; URINE
Structure of TIGECYCLINE GLUCURONIDE
METABOLITE -> PARENT
Major peak in feces
MAJOR
FECAL; PLASMA; URINE
Related Record Type Details
Structure of TIGECYCLINE, (4R)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MINOCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-AMINOMINOCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (4S,4AS,5AR,12AS)-9-AMINO-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE HYDROCHLORIDE
IMPURITY -> PARENT
Related Record Type Details
Structure of TIGECYCLINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

SINGLE DOSE

Volume of Distribution PHARMACOKINETIC AT STEADY-STATE

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