U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H41NO8
Molecular Weight 507.6163
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LATANOPROSTENE BUNOD

SMILES

O[C@H](CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)OCCCCO[N+]([O-])=O)CCC2=CC=CC=C2

InChI

InChIKey=LOVMMUBRQUFEAH-UIEAZXIASA-N
InChI=1S/C27H41NO8/c29-22(15-14-21-10-4-3-5-11-21)16-17-24-23(25(30)20-26(24)31)12-6-1-2-7-13-27(32)35-18-8-9-19-36-28(33)34/h1,3-6,10-11,22-26,29-31H,2,7-9,12-20H2/b6-1-/t22-,23+,24+,25-,26+/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H41NO8
Molecular Weight 507.6163
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Latanoprost (free acid) is a metabolite of latanoprost which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester prodrug which is converted to the Latanoprost-acid by endogenous esterase enzymes. The free acid is pharmacologically active and is 200 times more potent than latanoprost as an agonist of the human recombinant Prostaglandin F receptor. However, the free Latanoprost-acid is more irritating and less effective than Latanoprost when applied directly to the eyes of human glaucoma patients.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Mechanism of prostaglandin E2-, F2alpha- and latanoprost acid-induced relaxation of submental veins.
1997 Dec 11
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
2000 Jan 17
Latanoprostene Bunod 0.024% in Subjects With Open-angle Glaucoma or Ocular Hypertension: Pooled Phase 3 Study Findings.
2018 Jan
Patents

Sample Use Guides

In Vivo Use Guide
One drop in the affected eye(s) once daily in the evening
Route of Administration: Ocular
In Vitro Use Guide
HTMCs were seeded in 6-well plates at 2 x 10^5 cells/well in complete medium. When cells were confluent, they were incubated in low-serum medium overnight. Cells were pretreated with the phosphodiesterase inhibitor 3-isobutyl-1-methylxanthine (IBMX; 100 mkM) for 30 minutes and then exposed to LBN (Latanoprostene bunod) or latanoprost for 30 minutes. The NO donor SE 175 (100 mkM) was used as a positive control. Cells were treated with IBMX (100 mkM) plus the NO-independent activator of soluble guanylyl cyclase (sGC) 3-(5-hydroxymethyl-2-furyl)-benzylindazole (YC-1; 10 mkM) in conjunction with the drug and/or NO donor treatments. To determine the role of sGC in NO-induced cGMP elevation, cells were also preincubated with the sGC inhibitor ODQ (1 mkM) for 30 minutes. After the incubation period, cells were harvested. A cGMP enzyme immunoassay (Enzo Life Sciences, Farmingdale, NY, USA) was performed with the cell lysates. LBN (1–100 mkM) significantly increased cGMP levels in a dose-dependent manner, with a half maximal effective concentration (EC50) of 1.5 6 1.3 mkM, and with maximal effect similar to that of 100 mkM SE 175.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:25:53 UTC 2019
Edited
by admin
on Mon Oct 21 21:25:53 UTC 2019
Record UNII
I6393O0922
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LATANOPROSTENE BUNOD
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
PF-3187207
Code English
BOL-303259-X
Code English
LATANOPROSTENE BUNOD [WHO-DD]
Common Name English
VYZULTA
Brand Name English
NCX 116
Code English
LATANOPROSTENE BUNOD [INN]
Common Name English
4-(NITROOXY)BUTYL (5Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((3R)-3-HYDROXY-5-PHENYLPENTYL)CYCLOPENTYL)HEPT-5-ENOATE
Systematic Name English
LATANOPROSTENE BUNOD [USAN]
Common Name English
NCX-116
Code English
Code System Code Type Description
PUBCHEM
11156438
Created by admin on Mon Oct 21 21:25:53 UTC 2019 , Edited by admin on Mon Oct 21 21:25:53 UTC 2019
PRIMARY
INN
9629
Created by admin on Mon Oct 21 21:25:53 UTC 2019 , Edited by admin on Mon Oct 21 21:25:53 UTC 2019
PRIMARY
CAS
860005-21-6
Created by admin on Mon Oct 21 21:25:53 UTC 2019 , Edited by admin on Mon Oct 21 21:25:53 UTC 2019
PRIMARY
ChEMBL
CHEMBL2364612
Created by admin on Mon Oct 21 21:25:53 UTC 2019 , Edited by admin on Mon Oct 21 21:25:53 UTC 2019
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY