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220620-09-7 molecular structure
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(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

ChemBase ID: 442
Molecular Formular: C29H39N5O8
Molecular Mass: 585.64866
Monoisotopic Mass: 585.27986323
SMILES and InChIs

SMILES:
c1c(c(c2c(c1N(C)C)C[C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)O)NC(=O)CNC(C)(C)C
Canonical SMILES:
O=C(Nc1cc(N(C)C)c2c(c1O)C(=O)C1=C(O)[C@]3([C@@H](C[C@@H]1C2)[C@H](N(C)C)C(=C(C3=O)C(=O)N)O)O)CNC(C)(C)C
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
InChIKey:
FPZLLRFZJZRHSY-HJYUBDRYSA-N

Cite this record

CBID:442 http://www.chembase.cn/molecule-442.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
tigecycline
@tigecycline
Brand Name
Tygacil
Synonyms
(4R,4aS,5aR,12aS)-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-2-naphthacenecarboxamide
epi-TigecyclineDiscontinued
(4S,4aS,5aR,12aS)-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-2-naphthacenecarboxamide
WAY-GAR 936
Glycylcycline
GAR-936
WAY-GAR-936
GAR-936,Tigecycline
Tigecycline
Tygacil
TBG-MINO
CAS Number
220620-09-7
PubChem SID
46509041
160963905
PubChem CID
54686904
5282044

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.25205672  H Acceptors 11 
H Donor LogD (pH = 5.5) -5.231753 
LogD (pH = 7.4) -5.187741  Log P -5.147121 
Molar Refractivity 159.3431 cm3 Polarizability 59.23616 Å3
Polar Surface Area 205.76 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.66  LOG S -3.11 
Solubility (Water) 4.50e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Water expand Show data source
Apperance
Orange Solid expand Show data source
Melting Point
180-183°C (dec.) expand Show data source
Hydrophobicity(logP)
0.8 expand Show data source
Storage Condition
-20°C expand Show data source
Amber Vial, -20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Purity
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00560 external link
Item Information
Drug Groups approved
Description Tigecycline is a glycylcycline antibiotic developed and marketed by Wyeth under the brand name Tygacil. It was given a U.S. Food and Drug Administration (FDA) fast-track approval and was approved on June 17, 2005. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus.
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 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.
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.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation 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.
Half Life 27-43 hours
Protein Binding 71% to 89%
References
Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. [Pubmed]
Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1403 external link
Research Area: Skin and soft tissue infec
Biological Activity:
Tigecycline is a glycylcycline antibiotic. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus and acinetobacter baumanii. [1]
Toronto Research Chemicals - T440015 external link
A glycylcycline antibiotic, used to treat infection by drug resistant bacteria such as Staphylococcus aureus (Staph aureus) and Acinetobacter baumannii.
Toronto Research Chemicals - T440020 external link
An impurity of Tigecycline (T440015).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. Pubmed
  • • Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. Pubmed
  • • ] http://en.wikipedia.org/wiki/Tigecycline
  • • Lim, T., et al.: J. Antibiotics, 62, 675 (2009)
  • • Presterl, E., et al.: Antimicrob. Agents Chemother., 53, 3205 (2009)
  • • Varma, M., et al.: J. Med. Chem., 52, 4844 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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