5-trans Latanoprost (free acid)

Cayman Chemical Item Number 10129

5,6-trans Latanoprost (free acid) (CAS 903549-49-5)

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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 a ligand for the human recombinant FP receptor.2 5-trans Latanoprost (free acid) is an isomer of latanoprost (free acid) wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of latanoprost occurs as an impurity in commercial preparations of the bulk drug product. The present compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type prostaglandins, the biological activity of this isomer is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity, and on reducing intraocular pressure in particular, of 5-trans latanoprost.

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).

Synonyms
  • 5,6-trans Latanoprost (free acid)
Formal Name 9α,​11α,​15S-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prost-​5E-​en-​1-​oic acid
CAS Number 903549-49-5
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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O[C@@H]​(CCC1=CC=CC=C1)​CC[C@@H]​2[C@@H]​(C/C=C/CCCC(O)​=O)​[C@@H]​(O)​C[C@H]​2O
InCHI Code
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​1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)​14-15-20-19(21(25)​16-22(20)​26)​10-6-1-2-7-11-23(27)​28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)​/b6-1+/t18-,19+,20+,21-,22+/m0/s1
InCHI Key
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HNPFPERDNWXAGS-MIDWJBHHSA-N

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5-trans Latanoprost (free acid) is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $55.00 $0.00
5 mg $248.00 $0.00
10 mg $440.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2015-03-29. Prices are subject to change without notice.

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