A prodrug form of ampicillin
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Hetacillin

Item No. 35643

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,5R,6R)-6-((R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
3511-16-8
Molecular Formula
C19H23N3O4S
Formula Weight
389.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C1[C@](N2C([C@](C3=CC=CC=C3)([H])NC2(C)C)=O)([H])[C@]4([H])N1[C@H](C(C)(S4)C)C(O)=O
InChi Code
InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
InChi Key
DXVUYOAEDJXBPY-NFFDBFGFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Hetacillin is a prodrug form of the broad-spectrum antibiotic ampicillin (Item Nos. 14417 | 35740).1 It is converted to ampicillin via hydrolysis. Hetacillin is active against several bacteria, including E. coli, S. typhimurium, S. flexneri, H. influenzae, and S. pneumoniae (MICs = 2.5, 1.25, 2.5, 0.5, and 0.05 µg/ml, respectively). Intramammary administration of hetacillin increases the cure rate of bacterial infections in dairy cows.2 Formulations containing hetacillin have been used in the treatment of bovine mastitis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sutherland, R., and Robinson, O.P.W. Laboratory and pharmacological studies in man with hetacillin and ampicillin. Br. Med. J. 2(5555), 804-808 (1967).

    2. Vasquez, A.K., Nydam, D.V., Capel, M.B., et al. Randomized noninferiority trial comparing 2 commercial intramammary antibiotics for the treatment of nonsevere clinical mastitis in dairy cows. J. Dairy Sci. 99(10), 8267-8281 (2016).