Tigecycline

Identification

Summary

Tigecycline is a glycylcycline antibiotic used to treat a number of susceptible bacterial infections.

Brand Names
Tygacil
Generic Name
Tigecycline
DrugBank Accession Number
DB00560
Background

Tigecycline is a glycylcycline antibiotic developed and marketed by Wyeth under the brand name Tygacil. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus. It was granted fast-track approval by the U.S. Food and Drug Administration (FDA) on June 17, 2005.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 585.6487
Monoisotopic: 585.279863249
Chemical Formula
C29H39N5O8
Synonyms
  • (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
  • Tigeciclina
  • Tigecycline
  • Tigecyclinum
External IDs
  • CL-329998
  • CL-331002
  • DMG-DMDOT
  • DMG-MINO
  • GAR 936
  • GAR-936
  • TBG-MINO
  • WAY-GAR-936

Pharmacology

Indication

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Tigecycline is the first clinically-available drug in a new class of antibiotics called the glycylcyclines. Glycylcyclines are a new class of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. Glycylcycline antibiotics have a similar mechanism of action as tetracycline antibiotics. Both classes of antibiotics bind to the 30S ribosomal subunit to prevent the amino-acyl tRNA from binding to the A site of the ribosome. However, the glycylcyclines appear to bind more effectively than the tetracyclines.

Mechanism of action

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. Tigecycline is not affected by the two major tetracycline resistance mechanisms, ribosomal protection and efflux. Accordingly, tigecycline has demonstrated in vitro and in vivo activity against a broad spectrum of bacterial pathogens. There has been no cross resistance observed between tigecycline and other antibiotics. Tigecycline is not affected by resistance mechanisms such as beta-lactamases (including extended spectrum beta-lactamases), target site modifications, macrolide efflux pumps or enzyme target changes (e.g. gyrase/topoisomerase). In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterial drugs. In general, tigecycline is considered bacteriostatic.

TargetActionsOrganism
A16S ribosomal RNA
adduct
Enteric bacteria and other eubacteria
A30S ribosomal protein S9
adduct
Escherichia coli (strain K12)
A30S ribosomal protein S12
adduct
Escherichia coli (strain K12)
A30S ribosomal protein S13
adduct
Escherichia coli (strain K12)
A30S ribosomal protein S14
adduct
Escherichia coli (strain K12)
A30S ribosomal protein S19
adduct
Escherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

71% to 89%

Metabolism

Tigecycline is not extensively metabolized. In vitro studies with tigecycline using human liver microsomes, liver slices, and hepatocytes led to the formation of only trace amounts of metabolites. A glucuronide, an N-acetyl metabolite, and a tigecycline epimer (each at no more than 10% of the administered dose) are the primary metabolites.

Route of elimination

Not Available

Half-life

27-43 hours

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Since glycylcyclines are similar to tetracyclines, they share many of the same side effects and contraindications as tetracyclines. These side effects may include nausea/vomiting, headache, photosensitivity, discoloration of growing teeth, and fetal damage.

Pathways
PathwayCategory
Tigecycline Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Tigecycline.
AcitretinThe risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Tigecycline.
AlitretinoinThe risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Tigecycline.
AmoxicillinThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Tigecycline.
AmpicillinThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Tigecycline.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Tigecycline.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Tigecycline.
AzlocillinThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Tigecycline.
BacampicillinThe therapeutic efficacy of Bacampicillin can be decreased when used in combination with Tigecycline.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tigecycline.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TigecyclineInjection, powder, lyophilized, for solution50 mg/5mLIntravenousFresenius Kabi USA, LLC2016-12-01Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/5mLIntravenousAmneal Pharmaceuticals LLC2018-01-31Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/10mLIntravenousAccord Healthcare Inc.2019-03-28Not applicableUS flag
TigecyclinePowder, for solution50 mg / vialIntravenousApotex Corporation2014-10-23Not applicableCanada flag
Tigecycline AccordInjection, powder, for solution50 mgIntravenousAccord Healthcare S.L.U.2020-12-16Not applicableEU flag
Tigecycline AccordInjection, powder, for solution50 mgIntravenousAccord Healthcare S.L.U.2020-12-16Not applicableEU flag
Tigecycline for InjectionPowder, for solution50 mg / vialIntravenousNeo Health Canada Inc.Not applicableNot applicableCanada flag
TygacilInjection, powder, lyophilized, for solution50 mg/5mLIntravenousWyeth Pharmaceuticals Llc, a Subsidiary of Pfizer Inc.2017-02-08Not applicableUS flag
TygacilPowder, for solution50 mg / vialIntravenousPfizer Canada Ulc2006-11-30Not applicableCanada flag
TygacilInjection, powder, for solution50 mgIntravenousPfizer Europe Ma Eeig2016-09-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TigecyclineInjection, powder, lyophilized, for solution50 mg/5mLIntravenousMeitheal Pharmaceuticals Inc.2021-05-13Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/1IntravenousAuroMedics Pharma LLC2019-06-11Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/1IntravenousXellia Pharmaceuticals USA LLC2020-02-01Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/5mLIntravenousApotex Corp2019-04-09Not applicableUS flag
TigecyclineInjection, powder, lyophilized, for solution50 mg/10mLIntravenous; ParenteralSandoz Inc2017-11-30Not applicableUS flag

Categories

ATC Codes
J01AA20 — Combinations of tetracyclinesJ01AA12 — Tigecycline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Tetracyclines
Sub Class
Not Available
Direct Parent
Tetracyclines
Alternative Parents
Naphthacenes / Anthracenecarboxylic acids and derivatives / Alpha amino acid amides / Tetralins / Aryl ketones / Dialkylarylamines / N-arylamides / Aralkylamines / Cyclohexenones / Vinylogous acids
show 10 more
Substituents
Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Aryl ketone / Benzenoid
show 30 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tetracyclines (CHEBI:149836)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
70JE2N95KR
CAS number
220620-09-7
InChI Key
FPZLLRFZJZRHSY-HJYUBDRYSA-N
InChI
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
IUPAC Name
(4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
SMILES
[H][C@@]12CC3=C(C(O)=C(NC(=O)CNC(C)(C)C)C=C3N(C)C)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2

References

Synthesis Reference

Mahdi Fawzi, Tianmin Zhu, Syed Shah, "Tigecycline compositons and methods of preparation." U.S. Patent US20060247181, issued November 02, 2006.

US20060247181
General References
  1. Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. [Article]
  2. Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. [Article]
Human Metabolome Database
HMDB0014700
KEGG Drug
D01079
KEGG Compound
C12012
PubChem Compound
54686904
PubChem Substance
46509041
ChemSpider
10482314
BindingDB
50247905
RxNav
384455
ChEBI
149836
ChEMBL
CHEMBL376140
ZINC
ZINC000014879972
Therapeutic Targets Database
DAP000880
PharmGKB
PA164746412
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tigecycline
AHFS Codes
  • 08:12.24.12 — Glycylcyclines
FDA label
Download (170 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableBMI >30 kg/m21
4CompletedTreatmentAbdominal Abscess1
4CompletedTreatmentAbscess, Intra-Abdominal / Appendicitis / Diverticulitis / Gallbladder Inflammation / Intra-Abdominal Infections / Peritonitis1
4CompletedTreatmentAppendicitis / Cross Infection / Diverticulitis / Gallbladder Inflammation / Peritonitis1
4CompletedTreatmentInfection caused by staphylococci1
4CompletedTreatmentIntra-Abdominal Infections1
4CompletedTreatmentSkin Diseases, Bacterial1
4CompletedTreatmentSkin Diseases, Infectious1
4RecruitingTreatmentTreatment of Blood Stream Infections Due to Multidrug-Resistant Klebsiella Pneumoniae1
4Unknown StatusTreatmentAntibiotic Resistant Infection1

Pharmacoeconomics

Manufacturers
  • Wyeth pharmaceuticals inc
Packagers
  • Chongqing Carelife Pharmaceutical Co. Ltd.
  • Patheon Inc.
  • Wyeth Pharmaceuticals
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous50 mg/1vial
Powder50 mg/1vial
Injection, powder, for solutionIntravenous50 mg
InjectionIntravenous
InjectionParenteral
Powder, for solutionIntravenous
Powder, for solutionParenteral
Powder, for solution
Injection, powder, for solutionParenteral
Injection, powder, lyophilized, for solutionIntravenous50 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/1
Injection, powder, lyophilized, for solutionIntravenous; Parenteral50 mg/10mL
Powder, for solutionIntravenous50 mg / vial
Injection, solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous50 mg
Injection, powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Injection, powder, for solution50 mg/1vial
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
USRE40086No2008-02-192013-06-25US flag
CA2079692No2004-06-082012-10-02Canada flag
US8975242No2015-03-102028-10-24US flag
US8372995No2013-02-122030-10-08US flag
US9254328No2016-02-092026-03-13US flag
USRE40183No2008-03-252016-04-09US flag
US7879828No2011-02-012029-02-05US flag
US9694078No2017-07-042026-03-13US flag
US9855355No2018-01-022033-04-07US flag
US9855335No2018-01-022033-04-07US flag
US10588975No2006-03-132026-03-13US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 mg/mLALOGPS
logP0.66ALOGPS
logP-3.9ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area205.76 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity159.34 m3·mol-1ChemAxon
Polarizability61.56 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8344
Blood Brain Barrier-0.9836
Caco-2 permeable-0.5704
P-glycoprotein substrateSubstrate0.9098
P-glycoprotein inhibitor INon-inhibitor0.7651
P-glycoprotein inhibitor IINon-inhibitor0.895
Renal organic cation transporterNon-inhibitor0.9175
CYP450 2C9 substrateNon-substrate0.8283
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateSubstrate0.717
CYP450 1A2 substrateNon-inhibitor0.8705
CYP450 2C9 inhibitorNon-inhibitor0.882
CYP450 2D6 inhibitorNon-inhibitor0.9079
CYP450 2C19 inhibitorNon-inhibitor0.8592
CYP450 3A4 inhibitorNon-inhibitor0.9271
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8863
Ames testNon AMES toxic0.729
CarcinogenicityNon-carcinogens0.8718
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6895 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9926
hERG inhibition (predictor II)Non-inhibitor0.6739
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Adduct
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Trna binding
Specific Function
The C-terminal tail plays a role in the affinity of the 30S P site for different tRNAs. Mutations that decrease this affinity are suppressed in the 70S ribosome.
Gene Name
rpsI
Uniprot ID
P0A7X3
Uniprot Name
30S ribosomal protein S9
Molecular Weight
14856.105 Da
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Trna binding
Specific Function
Located at the top of the head of the 30S subunit, it contacts several helices of the 16S rRNA.In the E.coli 70S ribosome in the initiation state (PubMed:12809609) was modeled to contact the 23S rR...
Gene Name
rpsM
Uniprot ID
P0A7S9
Uniprot Name
30S ribosomal protein S13
Molecular Weight
13099.245 Da
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Structural constituent of ribosome
Specific Function
Binds 16S rRNA, required for the assembly of 30S particles and may also be responsible for determining the conformation of the 16S rRNA at the A site.
Gene Name
rpsN
Uniprot ID
P0AG59
Uniprot Name
30S ribosomal protein S14
Molecular Weight
11580.36 Da
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Adduct
General Function
Trna binding
Specific Function
In the E.coli 70S ribosome in the initiation state (PubMed:12809609) it has been modeled to contact the 23S rRNA of the 50S subunit forming part of bridge B1a; this bridge is broken in the model wi...
Gene Name
rpsS
Uniprot ID
P0A7U3
Uniprot Name
30S ribosomal protein S19
Molecular Weight
10430.235 Da
References
  1. Olson MW, Ruzin A, Feyfant E, Rush TS 3rd, O'Connell J, Bradford PA: Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66. [Article]
  2. da Silva LM, Nunes Salgado HR: Tigecycline: a review of properties, applications, and analytical methods. Ther Drug Monit. 2010 Jun;32(3):282-8. doi: 10.1097/FTD.0b013e3181dda54f. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 13, 2021 16:24