An internal standard for the quantification of tafluprost (free acid)
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Unlabeled Version(s)
10005439Tafluprost (free acid)
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Tafluprost (free acid)-d4

Item No. 9002406

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α-dihydroxy-15,15-difluoro-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic-3',3',4',4'-d4 acid
Synonyms
  • AFP-172-d4
Molecular Formula
C22H24D4F2O5
Formula Weight
414.5
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
218, 269, 276 nm
SMILES
O[C@@H](C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC2=CC=CC=C2)[C@@H]1C/C=C\C([2H])([2H])C([2H])([2H])CC(O)=O
InChi Code
InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+/t17-,18-,19+,20-/m1/s1/i2D2,7D2
InChi Key
KIQXRQVVYTYYAZ-CFBVNRQSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $49

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    500 µg

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    1 mg

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    Product Description

    Tafluprost (free acid)-d4 is intended for use as an internal standard for the quantification of tafluprost (free acid) (Item No. 10005439) by GC- or LC-MS. Tafluprost (free acid) is an FP receptor agonist (Ki = 4 nM for the human receptor), a derivative of prostaglandin F2α (PGF2α; Item Nos. 16010 | 16020), and an active metabolite of the prodrug tafluprost (Item No. 10005440).1 It is formed from tafluprost by hydrolysis and is selective for the FP receptor over the dopamine receptor and PGE2 receptor subtypes EP1 and EP2, as well as a panel of 32 neurological receptors and transporters, at 1 µM. Tafluprost (free acid) induces constriction in isolated cat iris sphincters (EC50 = 0.6 nM).2 It also increases the proliferation and migration of, capillary formation by, and COX-2 levels in, human umbilical vein endothelial cells (HUVECs) when used at a concentration of 100 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takagi, Y., Nakajima, T., Shimazaki, A., et al. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp. Eye Res. 78(4), 767-776 (2004).

    2. Nakajima, T., Matsugi, T., Goto, W., et al. New fluoroprostaglandin F2α derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol. Pharm. Bull. 26(12), 1691-1695 (2003).

    3. Roh, Y.J., Park, Y.G., Kang, S., et al. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch. Clin. Exp. Ophthalmol. 250(12), 1765-1775 (2012).