A latanoprost analog
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Latanoprost ethyl amide

Item No. 16822

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-ethyl-9α,11α,15R-trihydroxy-17-phenyl-18,19,20-trinor-prost-5Z-en-1-amide
CAS Number
607351-44-0
Synonyms
  • Lat-NEt
Molecular Formula
C25H39NO4
Formula Weight
417.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 50 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 200 µg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(N([H])CC)=O)[C@@H](CC[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C25H39NO4/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/h3,5-8,10-11,20-24,27-29H,2,4,9,12-18H2,1H3,(H,26,30)/b8-3-/t20-,21+,22+,23-,24+/m0/s1
InChi Key
KNXVTDOCIZLXFW-SQACBOECSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $81

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    5 mg

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    10 mg

    $633

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    Product Description

    Latanoprost ethyl amide (Lat-NEt) is a latanoprost analog in which the C-1 carboxyl group has been modified to an N-ethyl amide. Prostaglandin esters have been shown to have ocular hypotensive activity.1 Prostaglandin N-ethyl amides were recently introduced as alternative prostaglandin ocular hypotensive prodrugs.2 Although it has been claimed that prostaglandin ethyl amides are not converted to the free acids in vivo, studies in our laboratories have shown that bovine and human corneal tissue converts the N-ethyl amides of various prostaglandins to the free acids with a conversion rate of about 2.5 µg/g corneal tissue/hr.3,4 Lat-NEt would be expected to show the typical intraocular effects of Latanoprost free acid, but with the much slower hydrolysis pharmacokinetics of the prostaglandin N-amides.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp. Eye Res. 38(2), 181-184 (1984).

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

    3. Larrouy, D., Vidal, H., Andreelli, F., et al. Cloning and mRNA tissue distribution of human PPARγ coactivator-1. Int. J. Obes. Relat. Metab. Disord. 23(12), 1327-1332 (1999).

    4. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv. Ophthalmol. 47(Suppl. 1), S34-S40 (2002).