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PZ0021

Sigma-Aldrich

Tigecycline hydrate

≥98% (HPLC)

Synonym(s):

9-t-Butylglycylamido-minocycline hydrate, TBG-MINO, Tigecyclin, Tygacil

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About This Item

Empirical Formula (Hill Notation):
C29H39N5O8 · xH2O
CAS Number:
1229002-07-6
Molecular Weight:
585.65 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329823688
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -175 to -205°, c = 0.15 in methanol

color

off-white to yellow-brown

solubility

DMSO: ≥3 mg/mL (warmed)

storage temp.

2-8°C

SMILES string

O.CN(C)[C@H]1[C@@H]2C[C@@H]3Cc4c(cc(NC(=O)CNC(C)(C)C)c(O)c4C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)N(C)C

InChI

1S/C29H39N5O8.H2O/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);1H2/t12-,14-,21-,29-;/m0./s1

InChI key

PMPLAEFBZIFHAR-KXLOKULZSA-N

General description

Tigecycline is used to treat complicated skin and skin structure infections (cSSSI) and complicated intraabdominal infections.

Application

TIGECYCLINE HYDRATE has been used:
  • for antibiotic susceptibility testing
  • to study its effects on multiple nonsmall cell lung cancer (NSCLC) cell lines
  • to evaluate its effects on the binding of fluoroquinolones to human serum albumin
  • as a standard to investigate the penetration of tigecycline into cornea, aqueous humor and vitreous humor

Biochem/physiol Actions

Tigecycline is a broad spectrum glycylcycline antibiotic. Tigecycline is bacteriostatic, that inhibits protein synthesis by binding to the 30S ribosomal subunit of bacteria and thereby blocking entry of Aminoacyl-tRNA into the A site of the ribosome during prokaryotic translation. Tigecycline is active against resistant strains of gram-positive and gram-negative bacteria, avoiding the two most common mechanisms of resistance to the tetracycline antimicrobials: tetracycline efflux pump proteins and ribosomal protection proteins.

Other Notes

air sensitive

Signal Word

Danger

Hazard Statements

H317,H318,H360FD,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 2 - Eye Dam. 1 - Repr. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro activity of tigecycline against isolates from patients enrolled in phase 3 clinical trials of treatment for complicated skin and skin-structure infections and complicated intra-abdominal infections
Bradford PA, et al.
Clinical Infectious Diseases, 41 (2005)
Ocular penetration of topically applied 1% tigecycline in a rabbit model
Sakarya Y, et al.
International journal of ophthalmology, 10(5), 679-679 (2017)
Hubert Ziółkowski et al.
Poultry science, 99(10), 4750-4757 (2020-09-30)
Tetracyclines continue to be important antimicrobials in veterinary medicine. However, the pharmacokinetics (PK) of tigecycline (TIG) and minocycline (MIN) in broiler chickens has not been investigated to date, and the PK of chlortetracycline (CTC) and tetracycline (TET) remains insufficiently researched
The Effect of Tigecycline on the Binding of Fluoroquinolones to Human Serum Albumin
Jelic RM, et al.
Serbian Journal of Experimental and Clinical Research, 19(1), 17-25 (2018)
A Jasiecka-Mikołajczyk et al.
Journal of veterinary pharmacology and therapeutics, 41(1), e22-e29 (2017-08-24)
The aim of this research had been to determine the pharmacokinetics of tigecycline (TIG) in turkey after intravenous (i.v.), intramuscular (i.m.), subcutaneous (s.c.), and oral (p.o.) administration at a dose of 10 mg/kg. TIG concentrations in plasma were determined using high-performance
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