Isomer of bimatoprost
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5-trans-17-phenyl trinor Prostaglandin F2α ethyl amide

Item No. 10008132

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-ethyl-9α,11α,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5E,13E-dien-1-amide
CAS Number
1163135-95-2
Synonyms
  • 5-trans Bimatoprost
  • 5,6-trans-17-phenyl trinor PGF2α ethyl amide
Molecular Formula
C25H37NO4
Formula Weight
415.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
Acetonitrile: 3 mg/mlDMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 300 µg/ml
SMILES
O[C@@H]1[C@H](C/C=C/CCCC(NCC)=O)[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3+,17-16+/t20-,21+,22+,23-,24+/m0/s1
InChi Key
AQOKCDNYWBIDND-ABRBVVEGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

    $333

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    10 mg

    $589

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    25 mg

    $1,286

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    Product Description

    17-phenyl trinor Prostaglandin F2α (PGF2α) ethyl amide is an F-series PG analog which has been approved for use as an ocular hypotensive drug.1 5-trans-17-phenyl trinor PGF2α ethyl amide is an isomer of 17-phenyl trinor PGF2α ethyl amide wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of 17-phenyl trinor PGF2α ethyl amide occurs as an impurity in commercial preparations of the bulk drug product. The present compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type PGs, the biological activity of this isomer is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity of 5-trans-17-phenyl trinor PGF2α ethyl amide.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).

    Product Citations

    Zezula, M., Ruszczak, M., Maruszak, W., et al. Development and validation of the stability indicating RP-UHPLC method for the determination of the chemical purity and assay of bimatoprost. J. Pharm. Biomed. Anal. 174, 348-359 (2019).