An epimer of chlortetracycline
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4-epi-Chlortetracycline (hydrochloride)

Item No. 16663

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,6S)-7-chloro-4-(dimethylamino)-1,4,4aS,5,5aS,6,11,12a-octahydro-3,6,10,12,12aS-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, monohydrochloride
CAS Number
101342-45-4
Synonyms
  • 7-chloro-2-Naphthacenecarboxamide
Molecular Formula
C22H23ClN2O8 • HCl
Formula Weight
515.3
Purity
≥80%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 20 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
235, 255, 375 nm
SMILES
O=C1C2=C(O)C=CC(Cl)=C2[C@](O)(C)[C@]3([H])C1=C(O)[C@@](C(C(C(N)=O)=C(O)[C@@H]4N(C)C)=O)(O)[C@@]4([H])C3.Cl
InChi Code
InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7-,8-,15+,21-,22-;/m0./s1
InChi Key
CBHYYLPALVVVEY-QNUQNERCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    Chlortetracycline is an analog of tetracycline (Item No. 14328), a broad spectrum antibiotic. In addition to its actions against microorganisms, chlortetracycline suppresses inflammation by inhibiting neutrophil action and other aspects of the innate immune response.1,2,3,4 4-epi-Chlortetracycline is an epimer of chlortetracycline.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elferink, J.G., and Deierkauf, M. Inhibition of polymorphonuclear leukocyte functions by chlortetracycline. Biochem. Pharmacol. 33(22), 3667-3673 (1984).

    2. Akunda, J.K., Johnson, E., Ahrens, F.A., et al. Chlortetracycline modulates acute phase response of ex vivo perfused pig livers, and inhibits TNF-α secretion by isolated Kupffer cells. Comp. Immunol. Microbiol. Infect. Dis. 24(2), 81-89 (2001).

    3. Häyrinen-Immonen, R., Sorsa, T., Pettilä, J., et al. Effect of tetracyclines on collagenase activity in patients with recurrent aphthous ulcers. J. Oral Pathol. Med. 23(6), 269-272 (1994).

    4. Rasmussen, B., Noller, H.F., Daubresse, G., et al. Molecular basis of tetracycline action: Identification of analogs whose primary target is not the bacterial ribosome. Antimicrob. Agents Chemother. 35(11), 2306-2311 (1991).