Latanoprost acid Chemical Properties

Boiling point:

609.1±50.0 °C(Predicted)

Density 

1.159±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: freely soluble

form 

Oil

pka

4.76±0.10(Predicted)

color 

pale yellow, oil

optical activity

[α]/D 26.0 to 36.0°, c =0.1 in methanol

Stability:

Hygroscopic

InChIKey

HNPFPERDNWXAGS-NFVOFSAMSA-N

SMILES

C(O)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1

Safety Information

WGK Germany 

3

HS Code 

2937500000

MSDS

• Language:English Provider:SigmaAldrich

Latanoprost acid Usage And Synthesis

Description

Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. 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. Latanoprost is the isopropyl ester of a PGF_2α 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 PGF_2α. The efficacy of PG analog esters for the treatment of glaucoma correlates closely with the FP receptor binding affinity of the free acid. However, Lat-FA is more irritating and less effective than the prodrug latanoprost when applied directly to the eyes of human glaucoma patients.

Chemical Properties

Pale Yellow Oil

Uses

A metabolite of Latanoprost. Potent, selective FP prostanoid receptor agonist. F-series Prostaglandin analog. 200 times as potent as isopropyl ester form. Latanoprost USP Related Compound E.

Definition

ChEBI: Latanoprost free acid is a prostaglandin Falpha that is an analogue of prostaglandin F2alpha in which the pentyl group has been replaced by 2-phenylethyl and where the the 13,14-double bond has undergone formal hydrogenation. Its isopropyl ester prodrug, latanoprost, is used in the treatment of open-angle glaucoma and ocular hypertension. It has a role as an antiglaucoma drug, an antihypertensive agent and an EC 4.2.1.1 (carbonic anhydrase) inhibitor. It is a prostaglandins Falpha and a hydroxy monocarboxylic acid.

Biochem/physiol Actions

Potent, selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as isopropyl ester form.

References

[1] N A SHARIF. Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells.[J]. Journal of Ocular Pharmacology and Therapeutics, 2003, 19 6: 501-515. DOI: 10.1089/108076803322660422
[2] M. UNGRIN. Key structural features of prostaglandin E(2) and prostanoid analogs involved in binding and activation of the human EP(1) prostanoid receptor.[J]. Molecular Pharmacology, 2001, 59 6 1: 1446-1456. DOI: 10.1124/mol.59.6.1446
[3] NAJAM A SHARIF  Ata A A L  Ismail Kaddour Djebbar. Cat iris sphincter smooth-muscle contraction: comparison of FP-class prostaglandin analog agonist activities.[J]. Journal of Ocular Pharmacology and Therapeutics, 2008, 24 2: 152-163. DOI: 10.1089/jop.2007.0076

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