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Latanoprost (free acid)

Cayman Chemical Item Number 16811

PhXA-85; Lat-FA; 17-phenyl-13,14-dihydro trinor Prostaglandin F2α (CAS 41639-83-2)

Latanoprost (free acid) (CAS 41639-83-2)

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Description

Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug.1 Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as an FP receptor ligand for the human recombinant FP receptor.2 Latanoprost is the isopropyl ester of a PGF2α analog containing an aromatic group (17-phenyl) in the ω-chain. Lat-FA is the corresponding carboxylic acid of this analog. Lat-FA is a potent FP receptor agonist with an EC50 of 3.6 nM for human FP receptors, which is twice the potency of PGF2α. 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).

Synonyms
  • PhXA-85
  • Lat-FA
  • 17-phenyl-13,14-dihydro trinor Prostaglandin F2α
Formal Name 9α,​11α,​15R-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prost-​5Z-​en-​1-​oic acid
CAS Number 41639-83-2
Molecular Formula C23H34O5
Formula Weight 390.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC(CCc1ccccc1)​CC[C@H]​1C(O)​CC(O)​C1C/C=C\CCCC(=O)​O

Background Reading

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

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).

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

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).

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Latanoprost (free acid) 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
50 mg $1,855.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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