A glycylcycline antibiotic
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Labeled Version(s)
25414Tigecycline-d9
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Tigecycline

Item No. 15026

Technical Information
Formal Name
4S,7-bis(dimethylamino)-9-[[2-[(1,1-dimethylethyl)amino]acetyl]amino]-1,4S,4aS,5,5aR,6,11,12a-octahydro-3,10,12,12aS-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
CAS Number
220620-09-7
Synonyms
  • GAR 936
  • Glycylcycline
Molecular Formula
C29H39N5O8
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
251, 353 nm
SMILES
OC1=C(C(C2=C(O)[C@@](C(C(C(N)=O)=C(O)[C@H]3N(C)C)=O)(O)[C@@]3([H])C[C@]2([H])C4)=O)C4=C(N(C)C)C=C1NC(CNC(C)(C)C)=O
InChi Code
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 Key
FPZLLRFZJZRHSY-HJYUBDRYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tigecycline is a broad-spectrum glycylcycline antibiotic that binds to the bacterial 30S ribosome, blocking the entry of transfer RNA, which halts protein synthesis and inhibits bacterial growth.1 It is active against a panel of 1,924 European clinical bacterial isolates including S. aureus, S. epidermidis, S. pneumoniae, E. faecalis, E. faecium, E. coli, K. pneumoniae, P. aeruginosa, and P. mirabilis strains (MICs = <1-32 μg/ml).2 In vivo, tigecycline (6.25 mg/kg twice daily for 5 days) decreases levels of C. difficile cytotoxin activity and spore formation in cecum and colon in a mouse model of C. difficile infection.3 Formulations containing tigecycline have been used in the treatment of a variety of bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Greer, N.D. Tigecycline (Tygacil): The first in the glycylcycline class of antibiotics. Proc. (Bayl. Univ. Med. Cent.) 19(2), 155-161 (2006).

    2. Milatovic, D., Schmitz, F.J., Verhoef, J., et alActivities of the glycylcycline tigecycline (GAR-936) against 1,924 recent European clinical bacterial isolates. Antimicrob. Agents Chemother. 47(1), 400-404 (2003).

    3. Theriot, C.M., Schumacher, C.A., Bassis, C.M., et alEffects of tigecycline and vancomycin administration on established Clostridium difficile infection. Antimicrob. Agents Chemother. 59(3), 1596-1604 (2015).

    Product Citations

    Bergeson, S.E., Blanton, H., Martinez, J.M., et alBinge ethanol consumption increases inflammatory pain responses and mechanical and cold sensitivity: Tigecycline treatment efficacy shows sex differences. Alcohol Clin. Exp. Res. 40(12), 2506-2515 (2016).

    Pan, C.Y., Chen, J.C., Chen, T.L., et alPiscidin is highly active against carbapenem-resistant Acinetobacter baumannii and NDM-1-producing Klebsiella pneumonia in a systemic Septicaemia infection mouse model. Mar. Drugs 13(4), 2287-2305 (2015).