An alkaline phosphatase inhibitor
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L-p-Bromotetramisole (oxalate)

Item No. 18713

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6S)-6-(4-bromophenyl)-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole, monoethanedioate
CAS Number
62284-79-1
Synonyms
  • (-)-p-Bromotetramisole
  • L-para-Bromotetramisole
Molecular Formula
C11H11BrN2S • C2H2O4
Formula Weight
373.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
225, 228 nm
SMILES
BrC1=CC=C([C@H]2CN3C(SCC3)=N2)C=C1.OC(C(O)=O)=O
InChi Code
InChI=1S/C11H11BrN2S.C2H2O4/c12-9-3-1-8(2-4-9)10-7-14-5-6-15-11(14)13-10;3-1(4)2(5)6/h1-4,10H,5-7H2;(H,3,4)(H,5,6)/t10-;/m1./s1
InChi Key
ZULBIBHDIQCNIS-HNCPQSOCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $77

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    10 mg

    $120

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    25 mg

    $169

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    Product Description

    L-p-Bromotetramisole is a cell-permeable inhibitor of all four human AP isoenzymes (Kis =18 and 56 µM for PLAP and NSAP, respectively).1,2,3,4 While PLAP is strongly inhibited by L-p-bromotetramisole, a second AP, possibly PLAP-like, shows only partial inhibition.3 L-p-Bromotetramisole has been shown to inhibit a tyrosine phosphatase from Drosophila and, as a result, is also used as a tyrosine phosphatase inhibitor.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Denier, C.C., Brisson-Lougarre, A.A., Biasini, G.G., et al. Kinetic comparison of tissue non-specific and placental human alkaline phosphatases expressed in baculovirus infected cells: Application to screening for Down’s syndrome. BMC Biochem. 3:2, (2002).

    2. Van Belle, H., De Broe, M.E., and Wieme, R.J. L-p-Bromotetramisole, a new reagent for use in measuring placental or intestinal isoenzymes of alkaline phosphatase in human serum. Clin. Chem. 23(3), 454-459 (1977).

    3. Sakiyama, T., Robinson, J.C., and Chou, J.Y. Characterization of alkaline phosphatases from human first trimester placentas. The Journal of Biological Chemisty 254(3), 935-938 (1979).

    4. Doellgast, G.J., and Meis, P.J. Use of specific inhibitors to discriminate alkaline phosphatase isoenzymes originating from human liver, placenta and intestine: Absensce of meconial alkaline phosphatase in maternal serum. Clin. Chem. 25(7), 1230-1233 (1979).

    5. Fukami, Y., and Lipmann, F. Purification of a specific reversible tyrosine-O-phosphate phosphatase. Proc. Natl. Acad. Sci. USA 79(14), 4275-4279 (1982).

    6. Yingst, D.R., Davis, J., and Schiebinger, R. Inhibitors of tyrosine phosphatases block angiotensin II inhibition of Na(+) pump. Eur. J. Pharmacol. 461(1), 49-52 (2000).