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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
Structure of TIGECYCLINE HYDROCHLORIDE

SMILES

Cl.CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(O)=C(NC(=O)CNC(C)(C)C)C=C4N(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

HIDE SMILES / InChI
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

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
2588
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
117
Curator's Comment: # Wyeth Pharmaceuticals

Approval Year

2005
130
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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
8583
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
8583
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
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
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
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Disc. AE: Gastrointestinal disorder (NOS)...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorder (NOS) (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
DLT: Gastrointestinal disorder NOS...
Dose limiting toxicities:
Gastrointestinal disorder NOS
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
100 mg single, intravenous
MTD
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (50%)
Vomiting (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea
Vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Nausea
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
Vomiting
200 mg single, intravenous
MTD
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
healthy
Health Status: healthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/15616299
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
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
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021821s021lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP2C8
1057

CYP1A2
2153

P-gp
1741
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >100 uM]
CYP2C19
2141
 no [IC50 >100 uM]
CYP2C8
1117
 no [IC50 >100 uM]
CYP2C9
2497
 no [IC50 >100 uM]
CYP2D6
2546
 no [IC50 >100 uM]
CYP3A4
2633
 no [IC50 >100 uM]
P-gp
1932
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 inconclusive
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
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
eMolecules
6719081
https://www.emolecules.com/cgi-bin/more?vid=6719081
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
PubMed

PubMed

TitleDatePubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015-05-18
Tigecycline prevents LPS-induced release of pro-inflammatory and apoptotic mediators in neuronal cells.
2013-03
Fluorocyclines. 1. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: a potent, broad spectrum antibacterial agent.
2012-01-26
Prevalence of antimicrobial-resistant pathogens in Canadian hospitals: results of the Canadian Ward Surveillance Study (CANWARD 2008).
2010-11
Tigecycline attenuates staphylococcal superantigen-induced T-cell proliferation and production of cytokines and chemokines.
2009
Non-susceptibility trends among staphylococci from bacteraemias in the UK and Ireland, 2001-06.
2008-11
Meticillin-resistant Staphylococcus aureus hepatic abscess treated with tigecycline.
2008-08
Tigecycline: first of a new class of antimicrobial agents.
2006-08
Tigecycline: a new glycylcycline antimicrobial agent.
2006-07-01
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.
2002-10
Antimicrobial activity and spectrum of the new glycylcycline, GAR-936 tested against 1,203 recent clinical bacterial isolates.
2000-01
Disk diffusion susceptibility test development for the new glycylcycline, GAR-936.
1999-11
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 Wed Apr 02 05:20:13 GMT 2025
Edited
by admin
on Wed Apr 02 05:20:13 GMT 2025
Record UNII
7F4TZ17Y3R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIGECYCLINE MONOHYDROCHLORIDE
Preferred Name English
TIGECYCLINE HYDROCHLORIDE
Common Name English
2-NAPHTHACENECARBOXAMIDE, 4,7-BIS(DIMETHYLAMINO)-9-((2-((1,1-DIMETHYLETHYL)AMINO)ACETYL)AMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-, HYDROCHLORIDE (1:1), (4S,4AS,5AR,12AS)-
Systematic Name English
Code System Code Type Description
FDA UNII
7F4TZ17Y3R
Created by admin on Wed Apr 02 05:20:13 GMT 2025 , Edited by admin on Wed Apr 02 05:20:13 GMT 2025
PRIMARY
CAS
197654-04-9
Created by admin on Wed Apr 02 05:20:13 GMT 2025 , Edited by admin on Wed Apr 02 05:20:13 GMT 2025
PRIMARY
Related Record Type Details
Structure of TIGECYCLINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of TIGECYCLINE
ACTIVE MOIETY
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