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Cat. Number
653016613029022
Chemical Name
Latanoprost (free acid)-d4
References
Synonyms
  • PhXA 85-d4
  • 17-phenyl-13,14-dihydro trinor Prostaglandin F2α-d4
  • Lat-FA-d4
Formal Name 9α,​11α,​15R-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prost-​5Z-​en-​1-​oic-​3,​3,​4,​4-​d4 acid
Molecular Formula C23H30D4O5
Formula Weight 394.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated product
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES OC(CCc1ccccc1)​CC[C@H]​1C(O)​CC(O)​C1C/C=CCCCC(=O)​O

Background Reading

Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17 691-704 (1992).

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 285-293 (2000).

Sugamoto, K., Matsushita, Y., and Matsui, T. Facile and general method for preparation of (E)-4-hydroxy-2-alkenals. Lipids 32 903-905 (1997).

Camras, C.B., Alm, A., Watson, P., et al. Latanoprost, a prostaglandin analog, for glaucoma therapy. Efficacy and safety after 1 year of treatment in 198 patients. Ophthalmology 103 1916-1924 (1996).

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Size Global Purchasing
50 µg  
100 µg  
500 µg  
5 mg  

Description

Latanoprost (free acid)-d4 (Lat-FA-d4) contains four deuterium atoms at the 3, 3, 4, and 4 positions. It is intended for use as an internal standard for the quantification of Lat-FA by GC- or LC-mass spectrometry. Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug.1 It is the isopropyl ester of a PGF analog containing an aromatic group (17-phenyl) in the ω-chain. As an isopropyl ester, latanoprost acts as a prodrug which is converted to Lat-FA by endogenous esterase enzymes. Lat-FA is a potent FP receptor agonist with an EC50 value of 3.6 nM for human FP receptors, which is twice the potency of PGF and more than 200 times more potent latanoprost.2 The efficacy of PG analog esters for the treatment of glaucoma correlates closely with the FP receptor binding affinity of the free acid.3 However, Lat-FA is more irritating and less effective than the prodrug latanoprost when applied directly to the eyes of human glaucoma patients.4

1 Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17 691-704 (1992).

2 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 285-293 (2000).

3 Camras, C.B., Alm, A., Watson, P., et al. Latanoprost, a prostaglandin analog, for glaucoma therapy. Efficacy and safety after 1 year of treatment in 198 patients. Ophthalmology 103 1916-1924 (1996).

4 Sugamoto, K., Matsushita, Y., and Matsui, T. Facile and general method for preparation of (E)-4-hydroxy-2-alkenals. Lipids 32 903-905 (1997).

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