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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:10 UTC
HMDB IDHMDB0014700
Secondary Accession Numbers
  • HMDB14700
Metabolite Identification
Common NameTigecycline
DescriptionTigecycline, also known as way-gar-936 or GAR 936, 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. Tigecycline is a drug which is used 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 is a very strong basic compound (based on its pKa). In humans, tigecycline is involved in tigecycline action pathway. It was granted fast-track approval by the U.S. Food and Drug Administration (FDA) on June 17, 2005. In vitro studies have not demonstrated antagonism between tigecycline and other commonly used antibacterial drugs. Tigecycline is not extensively metabolized. Tigecycline is a glycylcycline antibiotic developed and marketed by Wyeth under the brand name Tygacil.
Structure
Data?1582753210
Synonyms
ValueSource
(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-naphthacenecarboxamideChEBI
GAR 936Kegg
WAY-gar-936Kegg
TygacilKegg
GAR-936HMDB
GAR-936,tigecyclineHMDB
Chemical FormulaC29H39N5O8
Average Molecular Weight585.6487
Monoisotopic Molecular Weight585.279863249
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
Traditional Nametigecycline
CAS Registry Number220620-09-7
SMILES
[H][C@@]12CC3=C(C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2)N(C)C
InChI Identifier
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
InChI KeyFPZLLRFZJZRHSY-HJYUBDRYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTetracyclines
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
Substituents
  • Tetracycline
  • Tetracene
  • Naphthacene
  • Anthracene carboxylic acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tetralin
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • N-arylamide
  • Aryl ketone
  • Aralkylamine
  • Cyclohexenone
  • Benzenoid
  • Tertiary alcohol
  • Vinylogous acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Primary carboxylic acid amide
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Enol
  • Polyol
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.45 g/LNot Available
LogP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP0.66ALOGPS
logP-5.1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.25ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area205.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity159.34 m³·mol⁻¹ChemAxon
Polarizability61.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-4001930000-22e69ebd79236f4379acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9100452000-f130a744591a63d492d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000160000-8205fe00cbeb220a3346Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000220000-30c34f7065bb152df678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9000100000-0d8aa036a2d02b9ba45bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000190000-29417938cf0db4088502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-009x-1200590000-8a5c06605779c6448948Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9306500000-bf7b1851bb25592d2a43Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00560 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00560 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00560
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482314
KEGG Compound IDC12012
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTigecycline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID149836
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. [PubMed:16790575 ]
  2. Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. [PubMed:16863487 ]
  3. Sader HS, Jones RN, Stilwell MG, Dowzicky MJ, Fritsche TR: Tigecycline activity tested against 26,474 bloodstream infection isolates: a collection from 6 continents. Diagn Microbiol Infect Dis. 2005 Jul;52(3):181-6. [PubMed:16105562 ]