A cephalosporin antibiotic building block
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7-Aminocephalosporanic Acid

Item No. 35824

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
957-68-6
Synonyms
  • 7-ACA
Molecular Formula
C10H12N2O5S
Formula Weight
272.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
CC(OCC1=C(C(O)=O)N(C([C@H]2N)=O)[C@]2([H])SC1)=O
InChi Code
InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m0/s1
InChi Key
HSHGZXNAXBPPDL-RCOVLWMOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 g

    $32

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    10 g

    $61

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    25 g

    $136

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    50 g

    $256

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    7-Aminocephalosporanic acid (7-ACA) is a building block of cephalosporin antibiotics, including cephalosporin C (Item No. 33262) and cefapirin (Item No. 17406).1,2 It binds to heat shock protein 90β (Hsp90β; Kd = 6.201 µM) and inhibits sterol regulatory element binding protein (SREBP) activation in a reporter assay using Hl 7702 cells when used at a concentration of 40 µM.3 7-ACA (40 µM) inhibits increases in total cholesterol and triglyceride levels induced by palmitic acid (Item No. 10006627) and oleic acid (Item Nos. 90260 | 24659) in HepG2 cells. It reduces hepatic steatosis in mice fed a high-fat diet when administered at doses ranging from 5 to 25 mg/kg. 7-ACA (10 mg/kg) inhibits the growth of M. leprae in mice.4 It is also a potential impurity in commercial preparations of cefoperazone.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Loder, B., Newton, G.G., and Abraham, E.P. The cephalosporin C nucleus (7-aminocephalosporanic acid) and some of its derivatives. Biochem. J. 79(2), 408-416 (1961).

    2. Crast, L.B., Jr, Graham, R.G., and Cheney, L.C. Synthesis of cephapirin and related cephalosporins from 7-(α-bromoacetamido)cephalosporanic acid. J. Med. Chem. 16(12), 1413-1415 (1973).

    3. Zhang, W., Xue, H., Zhou, C., et al. 7-aminocephalosporanic acid, a novel HSP90β inhibitor, attenuates HFD-induced hepatic steatosis. Biochem. Biophys. Res. Commun. 622, 184-191 (2022).

    4. Shepard, C.C., Van Landingham, R.M., Walker, L.L., et al. Activity of selected beta-lactam antibiotics against Mycobacterium leprae. Int. J. Lepr. Other Mycobact. Dis. 55(2), 322-327 (1987).

    5. Abdelaleem, E.A., Naguib, I.A., Zaazaa, H.E., et al. Development and validation of HPLC and HPTLC methods for determination of cefoperazone and its related impurities. J. Chromatogr. Sci. 54(2), 179-186 (2016).