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Latanoprostene Bunod

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Latanoprostene Bunod

Synopsis

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Chemistry

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Also known as: Vyzulta, 860005-21-6, Pf-3187207, Bol-303259-x, Ncx 116, Ncx-116

Molecular Formula

C₂₇H₄₁NO₈

Molecular Weight

507.6 g/mol

InChI Key

LOVMMUBRQUFEAH-UIEAZXIASA-N

FDA UNII

I6393O0922

Latanoprostene Bunod has been used in trials studying the treatment of Glaucoma, Ocular Hypertension, Open-Angle Glaucoma, Open Angle Glaucoma, and Intraocular Pressure. As of November 2, 2017 the FDA approved Bausch + Lomb's Vyzulta (latanoprostene bunod opthalmic solution), 0.024% for the indication of reducing intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Latanoprostene bunod is the first prostaglandin analog with one of its metabolites being nitric oxide (NO). The novelty of this agent subsequently lies in the proposed dual mechanism of action that stems from both its prostaglandin F2-alpha analog latanoprost acid metabolite and its ability to donate NO for proposed tissue/cell relaxation effects. In comparison, both latanoprost and latanoprostene bunod contain a latanoprost acid backbone. Conversely however, latanoprostene bunod integrates an NO-donating moiety in lieu of the isopropyl ester typically found in latanoprost.

1 2D Structure

Latanoprostene Bunod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-nitrooxybutyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

2.1.2 InChI

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

2.1.3 InChI Key

LOVMMUBRQUFEAH-UIEAZXIASA-N

2.1.4 Canonical SMILES

C1C(C(C(C1O)CC=CCCCC(=O)OCCCCO[N+](=O)[O-])CCC(CCC2=CC=CC=C2)O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@H]1O)C/C=C\CCCC(=O)OCCCCO[N+](=O)[O-])CC[C@H](CCC2=CC=CC=C2)O)O

2.2 Other Identifiers

2.2.1 UNII

I6393O0922

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bol 303259-x

2. Bol-303259-x

3. Bol303259-x

4. Ncx 116

5. Ncx-116

6. Ncx116

7. Pf 3187207

8. Pf-3187207

9. Pf3187207

2.3.2 Depositor-Supplied Synonyms

1. Vyzulta

2. 860005-21-6

3. Pf-3187207

4. Bol-303259-x

5. Ncx 116

6. Ncx-116

7. 4-nitrooxybutyl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

8. I6393o0922

9. 4-(nitrooxy)butyl (5z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((3r)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

10. Vesneo

11. Latanoprostene Bunod [inn]

12. Unii-i6393o0922

13. Latanoprostene Bunod [usan:inn]

14. Lbn

15. Vyzulta (tn)

16. Lbnncx116

17. Gtpl9635

18. Ncx116

19. Chembl2364612

20. Schembl12119560

21. Latanoprostene Bunod [mi]

22. Chebi:177703

23. Latanoprostene Bunod (usan/inn)

24. Dtxsid101027765

25. Latanoprostene Bunod [usan]

26. Bcp29385

27. Latanoprostene Bunod [who-dd]

28. Db11660

29. Hy-19518

30. Latanoprostene Bunod [orange Book]

31. Cs-0015617

32. D10441

33. Q27280492

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₄₁NO₈
Molecular Weight	507.6 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	18
Exact Mass	507.28321727 g/mol
Monoisotopic Mass	507.28321727 g/mol
Topological Polar Surface Area	142 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	646
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	VYZULTA
Active Ingredient	LATANOPROSTENE BUNOD
Company	BAUSCH AND LOMB (Application Number: N207795. Patents: 6211233, 7273946, 7629345, 7910767, 8058467)

4.2 Drug Indication

Latanoprostene bunod opthalmic solution is indicated for the reduction of intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Upon applying an appropriate dose of latanoprost bunod, reduction in intraocular pressure begins approximately 1 to 3 hours later with a maximum intraocular pressure reduction effect demonstrated after 11 to 13 hours.

5.2 ATC Code

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EE - Prostaglandin analogues

S01EE06 - Latanoprostene bunod

5.3 Absorption, Distribution and Excretion

Absorption

In a study with 22 healthy subjects monitored for 28 days, there were no quantifiable plasma concentrations of latanoprostene bunod (Lower Limit Of Quantitation, LLOQ, of 10.0 pg/mL) or butanediol mononitrate (LLOQ of 200 pg/mL) post daily dose of one drop bilaterally in the morning on Day 1 and 28. The mean time of maximum plasma concentration (Tmax) for latanoprost acid was about 5 minutes post dosage on both Day 1 and 28 of therapy. The mean maximum plasma concentrations (Cmax) of latanoprost acid (LLOQ of 30 pg/mL) were 59.1 pg/mL on Day 1 and 28, respectively.

Route of Elimination

The latanoprost acid component of latanoprostene bunod is predominantly metabolized by the liver and excreted primarily in the urine.

Volume of Distribution

Unfortunately there have been no formal ocular distribution studies performed in humans at this time.

Clearance

Since latanoprost acid plasma concentration dropped below the LLOQ (Lower Limit Of Quantitation) of 30 pg/mL in the majority of study subjects by 15 minutes following ordinary ocular administration, the elimination of latanoprost acid from human plasma is considered rapid.

5.4 Metabolism/Metabolites

Upon topical administration at the ocular surface, latanoprostene bunod undergoes rapid carboxyl ester hydrolysis by endogenous corneal esterases into latanoprost acid and butanediol mononitrate. After the latanoprost acid reaches the systemic circulation, it is largely metabolized by the liver to the 1,2-dinor and 1,2,3,4-tetranor metabolites by way of fatty acid beta-oxidation. The butanediol monohidrate undergoes further metabolism (reduction) to 1,4-butanediol and nitric oxide (NO). Furthermore, this 1,4-butanediol metabolite is further oxidized to succinic acid that is subsequently then primarily taken up as a component in the tricarboxylic acid (TCA) cycle in cellular aerobic respiration.

5.5 Biological Half-Life

The half-life after application of latanoprostene bunod in rabbits was 1.8 hours in cornea, 2.1 hours in aqueous humor, and 4.6 hours in the iris/ciliary body.

5.6 Mechanism of Action

Open-angle glaucoma (OAG) is a medical condition that is associated with progressive visual field damage and the loss of vision. Occular hypertension (OHT) is considered a key risk factor for OAG and reducing intraocular pressure (IOP) and being able to maintain unique and appropriate target IOPs for various different patients having OHT can delay or prevent the onset of primary OAG or slow the disease progression of established glaucoma. Ordinary physiological IOP results from aqueous humor produced by the ocular ciliary body and its outflow through a) the trabecular meshwork (TM) and Schlemm's canal (SC) in what is called the conventional pathway, and b) the uveoscleral pathway via the ciliary muscle/choroid/sclera in what is refered to as the unconventional pathway. In patients with OHT or OAG there is increased resistance to aqueous humor outflow by way of the TM/SC pathway, which causes increased IOP. This increase in IOP is believed to be the cause of mechanical stress on the posterior structures of the eye which can result in the dysfunction of optic nerve fibers and the destruction of retinal ganglion cells - all of which ultimately contributes to vision loss. As there is no cure for glaucoma, therapeutic management is predominantly focused on minimizing disease progression and clinical sequelae via the reduction and maintainenance of appropriate target IOPs. Subsequently, latanoprostene bunod is thought to lower intraocular pressure via a dual mechanism of action since the medication is metabolized into two relevant moieties upon administration: (1) latanoprost acid, and (2) butanediol mononitrate. As a prostaglandin F2-alpha analog, the latanoprost acid moiety operates as a selective PGF2-alpha (FP) receptor agonist. Since FP receptors occur in the ciliary muscle, ciliary epithelium, and sclera the latanoprost acid moiety primarily acts in the uveoscleral pathway where it increases the expression of matrix metalloproteinases (MMPs) like MMP-1, -3, and -9 which promote the degradation of collagen types I, III, and IV in the longitudinal bundles of the ciliary musicle and surrounding sclera. The resultant extracellular matrix remodeling of the ciliary muscle consequently produces reduced outflow resistance via increased permeability and increased aqueous humor outflow through the uveoscleral route. Conversely, the butanediol mononitrate undergoes further metabolism to NO and an inactive 1,4-butanediol moiety. As a gas that can freely diffuse across plasma membranes, it is proposed that the relaxing effect of NO to induce reductions in the cell volume and contractility of vascular smooth muscle like cells is dependant upon activation of the sGC/cGMP/PKG cascade pathway. NO released from butanediol mononitrate consequently enters the cells of the TM and inner wall of SC, causing decreases in myosin light chain-2 phosphorylation, increased phosphorylation of large-conductance calcium-activated potassium (BKCa) channels, and a subsequent efflux of potassium ions through such BKCa channels. All of these changes serve to decrease the cell contractility and volume, as well as to rearrange the actin cytoskeleton of the TM and SC cells. These biomechanical changes ultimately allow for enhanced conventional outflow of aqueous humor.

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