An impurity generated during bulk production of misoprostol
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11β-Misoprostol

Item No. 13825

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11β,16-dihydroxy-16-methyl-prost-13E-en-1-oic acid, methyl ester
CAS Number
58717-36-5
Molecular Formula
C22H38O5
Formula Weight
382.5
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
CCCCC(O)(C)C/C=C/[C@H]([C@H]1CCCCCCC(OC)=O)[C@@H](O)CC1=O
InChi Code
InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20+,22?/m1/s1
InChi Key
OJLOPKGSLYJEMD-XRULAAHKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $194

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    1 mg

    $366

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    Product Description

    Misoprostol is a widely sold analog of prostaglandin E1 (PGE1) which has potent but relatively non-selective agonist activity with respect to the prostanoid EP receptor subgroup.1 Misoprostol has been used therapeutically for many years in humans for the treatment of gastric ulcer disease under the Searle tradename Cytotec.2 11β-Misoprostol is one of several impurities which are possible in the production of commercial lots of bulk misoprostol, and is somewhat difficult to distinguish from other impurities such as 8-iso misoprostol. The pharmacology and EP receptor binding affinity for 11β-misoprostol have not been published.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim. Biophys. Acta 1483(2), 285-293 (2000).

    2. Collins, P.W. Misoprostol: Discovery, development, and clinical applications. Med. Res. Rev. 10(2), 149-172 (1990).