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MedKoo Cat#: 561500 | Name: PF-3187207
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Latanoprostene, also known as PF-3187207, is a a nitric oxide (NO)-donating latanoprost with prostaglandin activity. It loweres intraocular pressure (IOP) more effectively than latanoprost in monkeys, dogs and rabbits.

Chemical Structure

PF-3187207
PF-3187207
CAS#860005-21-6

Theoretical Analysis

MedKoo Cat#: 561500

Name: PF-3187207

CAS#: 860005-21-6

Chemical Formula: C27H41NO8

Exact Mass: 507.2832

Molecular Weight: 507.62

Elemental Analysis: C, 63.89; H, 8.14; N, 2.76; O, 25.21

Price and Availability

Size Price Availability Quantity
1mg USD 90.00 Ready to ship
5mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 1,950.00 Ready to ship
500mg USD 3,850.00 Ready to ship
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Related CAS #
No Data
Synonym
PF-3187207; PF3187207; PF 3187207; Latanoprostene BUNOD; BOL-303259-X; NCX-116; NCX116; NCX116; Vesneo; Vyzulta;
IUPAC/Chemical Name
4-Nitrooxybutyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
InChi Key
LOVMMUBRQUFEAH-UIEAZXIASA-N
InChi Code
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
SMILES Code
O=C(OCCCCO[N+]([O-])=O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C[C@@H]1O
Appearance
Colorless to light yellow liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Latanoprostene bunod (LBN), a nitric oxide (NO)-donating prostaglandin F2a analog, is a topical ophthalmic therapeutic for the reduction of intraocular pressure (IOP).
In vitro activity:
There was a significant increase in cGMP levels with 1, 3, 10, 30, and 100 μM LBN (Figs. 2A, 2C) and also with the NO donor SE 175 at both 10 and 100 μM (Figs. 2A, 2B). In contrast, there was no statistically significant effect of latanoprost on cGMP levels, except at 100 μM, when a small (approximately 60%) yet significant increase was observed (Fig. 2A). The EC50 for LBN for induction of HTMC cGMP levels was 1.5 ± 0.3 μM, and maximal efficacy was 320 ± 13%, whereas the EC50 for latanoprost could not be determined for the concentrations evaluated. To confirm the involvement of sGC in the elevation of cGMP levels by the two NO donors, the effect of the specific sGC inhibitor ODQ was determined. Incubation of HTMCs with ODQ (1 μM) prevented SE 175 and LBN induced cGMP generation (Figs. 2B, 2C). Reference: Invest Ophthalmol Vis Sci. 2015 Jun;56(6):4108-16. https://pubmed.ncbi.nlm.nih.gov/26114488/
In vivo activity:
Rabbits are known to be sensitive to most IOP-lowering agents except for PGF2α agonists which makes this model ideal to dissect out NO-mediated effects for BOL-303259-X (PF3187207). The injection of 0.1 ml of hypertonic saline into the vitreous body led to a rapid (Tmax, 0.5 h) IOP rise from 16.9 ± 1.9 (baseline) to 45 ± 2.2 mmHg (Fig. 1) that decayed toward baseline over the following 5 h. BOL-303259-X (0.036%) significantly attenuated the saline-induced IOP rise throughout the experimental period (Fig. 1). The effects were maximal between 0.5 and 1.5 h with an average IOP difference versus vehicle of −13.5 ± 2.0 mmHg (−30%) (Fig. 1). As expected, an equimolar dose (0.030%) of latanoprost did not result in appreciable effects in this model. Reference: Exp Eye Res. 2011 Sep;93(3):250-5. https://pubmed.ncbi.nlm.nih.gov/21396362/
Solvent mg/mL mM comments
Solubility
DMSO 30.0 59.10
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 507.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Cavet ME, Vollmer TR, Harrington KL, VanDerMeid K, Richardson ME. Regulation of Endothelin-1-Induced Trabecular Meshwork Cell Contractility by Latanoprostene Bunod. Invest Ophthalmol Vis Sci. 2015 Jun;56(6):4108-16. doi: 10.1167/iovs.14-16015. PMID: 26114488. 2. Krauss AH, Impagnatiello F, Toris CB, Gale DC, Prasanna G, Borghi V, Chiroli V, Chong WK, Carreiro ST, Ongini E. Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating prostaglandin F2α agonist, in preclinical models. Exp Eye Res. 2011 Sep;93(3):250-5. doi: 10.1016/j.exer.2011.03.001. Epub 2011 Mar 9. PMID: 21396362.
In vitro protocol:
1. Cavet ME, Vollmer TR, Harrington KL, VanDerMeid K, Richardson ME. Regulation of Endothelin-1-Induced Trabecular Meshwork Cell Contractility by Latanoprostene Bunod. Invest Ophthalmol Vis Sci. 2015 Jun;56(6):4108-16. doi: 10.1167/iovs.14-16015. PMID: 26114488. 2. Krauss AH, Impagnatiello F, Toris CB, Gale DC, Prasanna G, Borghi V, Chiroli V, Chong WK, Carreiro ST, Ongini E. Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating prostaglandin F2α agonist, in preclinical models. Exp Eye Res. 2011 Sep;93(3):250-5. doi: 10.1016/j.exer.2011.03.001. Epub 2011 Mar 9. PMID: 21396362.
In vivo protocol:
1. Krauss AH, Impagnatiello F, Toris CB, Gale DC, Prasanna G, Borghi V, Chiroli V, Chong WK, Carreiro ST, Ongini E. Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating prostaglandin F2α agonist, in preclinical models. Exp Eye Res. 2011 Sep;93(3):250-5. doi: 10.1016/j.exer.2011.03.001. Epub 2011 Mar 9. PMID: 21396362.
1: El-Nimri NW, Moghimi S, Penteado RC, Ghahari E, Yang D, Brye N, Proudfoot J, Do JL, Camp A, Salcedo M, Rubio V, Weinreb RN. Comparison of the Effects of Latanoprostene Bunod and Timolol on Retinal Blood Vessel Density: A Randomized Clinical Trial. Am J Ophthalmol. 2022 Sep;241:120-129. doi: 10.1016/j.ajo.2022.04.022. Epub 2022 May 6. PMID: 35526590; PMCID: PMC9444916. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Latanoprostene Bunod. 2022 Apr 18. PMID: 30000019. 3: Bahr T, Woolf S, Favre H, Waldman C. Comparison of netarsudil and latanoprostene bunod as adjuncts to maximum medical therapy in primary open- angle glaucoma. Can J Ophthalmol. 2023 Aug;58(4):356-360. doi: 10.1016/j.jcjo.2022.03.004. Epub 2022 Apr 11. PMID: 35421360. 4: Desai SJ, Pumphrey SA, Koethe B. Comparative effects of latanoprost and latanoprostene bunod on intraocular pressure and pupil size in ophthalmologically normal Beagle dogs. Vet Ophthalmol. 2022 Jul;25(4):282-290. doi: 10.1111/vop.12982. Epub 2022 Mar 5. PMID: 35247289. 5: Samaha D, Diaconu V, Bouchard JF, Desalliers C, Dupont A. Effect of Latanoprostene Bunod on Optic Nerve Head Blood Flow. Optom Vis Sci. 2022 Feb 1;99(2):172-176. doi: 10.1097/OPX.0000000000001842. PMID: 34889858. 6: Radell JE, Sharma HK, Auyeung KL, Paul ME, Gagliuso DJ, Chadha N, Tsai JC, Serle JB. Two-Year Experience With Latanoprostene Bunod in Clinical Practice. J Glaucoma. 2021 Sep 1;30(9):776-780. doi: 10.1097/IJG.0000000000001904. PMID: 34172630. 7: Hébert M, Gravel JF, You E, Qi SR, Lajoie C. Cystoid macular edema secondary to latanoprostene bunod. Can J Ophthalmol. 2021 Dec;56(6):e185-e187. doi: 10.1016/j.jcjo.2021.04.011. Epub 2021 May 25. PMID: 34048726. 8: Mehta AA, Kanu LN, Sood-Mendiratta S, Quinones R, Hawkins A, Lehrer RA, Malhotra K, Papas R, Hillman D, Wilensky JT, Aref AA, Vajaranant TS, Edward DP. Experience with netarsudil 0.02% and latanoprostene bunod 0.024% as adjunctive therapy for glaucoma. Eur J Ophthalmol. 2022 Jan;32(1):322-326. doi: 10.1177/1120672121998913. Epub 2021 Mar 2. PMID: 33653172. 9: Harasymowycz P, Royer C, Cui AX, Barbeau M, Jobin-Gervais K, Mathurin K, Lachaine J, Beauchemin C. Short-term efficacy of latanoprostene bunod for the treatment of open-angle glaucoma and ocular hypertension: a systematic literature review and a network meta-analysis. Br J Ophthalmol. 2022 May;106(5):640-647. doi: 10.1136/bjophthalmol-2020-317262. Epub 2021 Jan 4. PMID: 33397657; PMCID: PMC9046749. 10: Ostler E, Rhee D, Burney E, Sozeri Y. Advances in medical therapy for glaucoma. Curr Opin Ophthalmol. 2021 Mar 1;32(2):129-133. doi: 10.1097/ICU.0000000000000740. PMID: 33395110. 11: Wang Y, Liao Y, Nie X. Comparative evaluation of Latanoprostene Bunod, Timolol Maleate, and latanoprost Ophthalmic Solutions to assess their safety and efficacy in lowering intraocular pressure for the management of Open-Angle Glaucoma. Clinics (Sao Paulo). 2020 Nov 30;75:e1874. doi: 10.6061/clinics/2020/e1874. PMID: 33263632; PMCID: PMC7688071. 12: Patel PD, Kasetti RB, Sonkusare SK, Zode GS. Technical brief: Direct, real- time electrochemical measurement of nitric oxide in ex vivo cultured human corneoscleral segments. Mol Vis. 2020 Jun 5;26:434-444. PMID: 32565671; PMCID: PMC7300198. 13: Mehran NA, Sinha S, Razeghinejad R. New glaucoma medications: latanoprostene bunod, netarsudil, and fixed combination netarsudil-latanoprost. Eye (Lond). 2020 Jan;34(1):72-88. doi: 10.1038/s41433-019-0671-0. Epub 2019 Nov 6. PMID: 31695162; PMCID: PMC7002400. 14: Fingeret M, Gaddie IB, Bloomenstein M. Latanoprostene bunod ophthalmic solution 0.024%: a new treatment option for open-angle glaucoma and ocular hypertension. Clin Exp Optom. 2019 Nov;102(6):541-550. doi: 10.1111/cxo.12853. Epub 2019 Jan 7. PMID: 30614563; PMCID: PMC6899723. 15: Hussar DA. New Drugs 2018, part 3. Nursing. 2018 Oct;48(10):32-43. doi: 10.1097/01.NURSE.0000545013.60672.65. PMID: 30192268. 16: Two new drugs for glaucoma. Med Lett Drugs Ther. 2018 Jul 16;60(1551):117-120. PMID: 30036347. 17: Hoy SM. Latanoprostene Bunod Ophthalmic Solution 0.024%: A Review in Open- Angle Glaucoma and Ocular Hypertension. Drugs. 2018 May;78(7):773-780. doi: 10.1007/s40265-018-0914-6. Erratum in: Drugs. 2018 Jun;78(8):857. doi: 10.1007/s40265-018-0925-3. PMID: 29761382; PMCID: PMC5976683. 18: Andrés-Guerrero V, García-Feijoo J. Nitric oxide-donating compounds for IOP lowering in glaucoma. Arch Soc Esp Oftalmol (Engl Ed). 2018 Jun;93(6):290-299. English, Spanish. doi: 10.1016/j.oftal.2018.02.004. Epub 2018 Mar 23. PMID: 29580758. 19: Weinreb RN, Liebmann JM, Martin KR, Kaufman PL, Vittitow JL. Latanoprostene Bunod 0.024% in Subjects With Open-angle Glaucoma or Ocular Hypertension: Pooled Phase 3 Study Findings. J Glaucoma. 2018 Jan;27(1):7-15. doi: 10.1097/IJG.0000000000000831. PMID: 29194198; PMCID: PMC7654727. 20: Liebmann JM, Lee JK. Current therapeutic options and treatments in development for the management of primary open-angle glaucoma. Am J Manag Care. 2017 Sep;23(15 Suppl):S279-S292. PMID: 29164845.