Latanoprost ethyl amide

Cayman Chemical Item Number 16822

Lat-NEt (CAS 607351-44-0)

Latanoprost ethyl amide (CAS 607351-44-0)

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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,3 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.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.

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

2 Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of Bimatoprost (Lumigan™). Surv Ophthalmol 45 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 23 1327-1332 (1999).

4 Maxey, K.M., Johnson, J., Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol 47(4) 34-40 (2002).

Synonyms
  • Lat-NEt
Formal Name N-​ethyl-​9α,​11α,​15R-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prost-​5Z-​en-​1-​amide
CAS Number 607351-44-0
Molecular Formula C25H39NO4
Formula Weight 417.6
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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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
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​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
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KNXVTDOCIZLXFW-SQACBOECSA-N

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Latanoprost ethyl amide is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $53.00 $0.00
5 mg $239.00 $0.00
10 mg $424.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-23. Prices are subject to change without notice.

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