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MedKoo Cat#: 319798 | Name: Taprenepag
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Description:

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

Taprenepag, also known as CP-544326, is a potent and selective EP(2) receptor agonist, was successfully evaluated for its ocular hypotensive activity in a clinical study involving patients with primary open angle glaucoma. Taprenepag is the active metabolite of PF-04217329.

Chemical Structure

Taprenepag
Taprenepag
CAS#752187-80-7

Theoretical Analysis

MedKoo Cat#: 319798

Name: Taprenepag

CAS#: 752187-80-7

Chemical Formula: C24H22N4O5S

Exact Mass: 478.1311

Molecular Weight: 478.52

Elemental Analysis: C, 60.24; H, 4.63; N, 11.71; O, 16.72; S, 6.70

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,650.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 5,250.00 2 Weeks
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Related CAS #
752187-80-7 (free) 1005549-94-9 (isopropyl)
Synonym
CP-544326; CP544326, CP544326, Taprenepag, PF-0421732 metabolite
IUPAC/Chemical Name
2-(3-((N-(4-(1H-pyrazol-1-yl)benzyl)pyridine-3-sulfonamido)methyl)phenoxy)acetic acid
InChi Key
MFFBXYNKZHTCEY-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H22N4O5S/c29-24(30)18-33-22-5-1-4-20(14-22)17-27(34(31,32)23-6-2-11-25-15-23)16-19-7-9-21(10-8-19)28-13-3-12-26-28/h1-15H,16-18H2,(H,29,30)
SMILES Code
O=C(O)COC1=CC=CC(CN(CC2=CC=C(N3N=CC=C3)C=C2)S(=O)(C4=CC=CN=C4)=O)=C1
Appearance
Solid powder
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, not in water
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

Preparing Stock Solutions

The following data is based on the product molecular weight 478.52 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
1: Kaplan TM, Sit AJ. Emerging drugs for the treatment of glaucoma: a review of phase II & III trials. Expert Opin Emerg Drugs. 2022 Sep;27(3):321-331. doi: 10.1080/14728214.2022.2110240. Epub 2022 Aug 12. PMID: 35924872. 2: Garcia H, Serafin AS, Silbermann F, Porée E, Viau A, Mahaut C, Billot K, Birgy É, Garfa-Traore M, Roy S, Ceccarelli S, Mehraz M, Rodriguez PC, Deleglise B, Furio L, Jabot-Hanin F, Cagnard N, Del Nery E, Fila M, Sin-Monnot S, Antignac C, Lyonnet S, Krug P, Salomon R, Annereau JP, Benmerah A, Delous M, Briseño-Roa L, Saunier S. Agonists of prostaglandin E2 receptors as potential first in class treatment for nephronophthisis and related ciliopathies. Proc Natl Acad Sci U S A. 2022 May 3;119(18):e2115960119. doi: 10.1073/pnas.2115960119. Epub 2022 Apr 28. PMID: 35482924; PMCID: PMC9170064. 3: Qu C, Mao C, Xiao P, Shen Q, Zhong YN, Yang F, Shen DD, Tao X, Zhang H, Yan X, Zhao RJ, He J, Guan Y, Zhang C, Hou G, Zhang PJ, Hou G, Li Z, Yu X, Chai RJ, Guan YF, Sun JP, Zhang Y. Ligand recognition, unconventional activation, and G protein coupling of the prostaglandin E2 receptor EP2 subtype. Sci Adv. 2021 Apr 2;7(14):eabf1268. doi: 10.1126/sciadv.abf1268. PMID: 33811074; PMCID: PMC11057787. 4: Impagnatiello F, Bastia E, Almirante N, Brambilla S, Duquesroix B, Kothe AC, Bergamini MVW. Prostaglandin analogues and nitric oxide contribution in the treatment of ocular hypertension and glaucoma. Br J Pharmacol. 2019 Apr;176(8):1079-1089. doi: 10.1111/bph.14328. Epub 2018 May 24. PMID: 29669171; PMCID: PMC6451067. 5: Yanochko GM, Affolter T, Eighmy JJ, Evans MG, Khoh-Reiter S, Lee D, Miller PE, Shiue MH, Trajkovic D, Jessen BA. Investigation of ocular events associated with taprenepag isopropyl, a topical EP2 agonist in development for treatment of glaucoma. J Ocul Pharmacol Ther. 2014 Jun;30(5):429-39. doi: 10.1089/jop.2013.0222. Epub 2014 Apr 10. PMID: 24720348. 6: Schachar RA, Raber S, Thomas KV, Benetz BA, Szczotka-Flynn LB, Zhang M, Howell SJ, Lass JH. Subclinical increased anterior stromal reflectivity with topical taprenepag isopropyl. Cornea. 2013 Mar;32(3):306-12. doi: 10.1097/ICO.0b013e3182523f40. PMID: 22549238; PMCID: PMC4856027. 7: Schachar RA, Raber S, Courtney R, Zhang M. A phase 2, randomized, dose- response trial of taprenepag isopropyl (PF-04217329) versus latanoprost 0.005% in open-angle glaucoma and ocular hypertension. Curr Eye Res. 2011 Sep;36(9):809-17. doi: 10.3109/02713683.2011.593725. PMID: 21851167. 8: Prasanna G, Carreiro S, Anderson S, Gukasyan H, Sartnurak S, Younis H, Gale D, Xiang C, Wells P, Dinh D, Almaden C, Fortner J, Toris C, Niesman M, Lafontaine J, Krauss A. Effect of PF-04217329 a prodrug of a selective prostaglandin EP(2) agonist on intraocular pressure in preclinical models of glaucoma. Exp Eye Res. 2011 Sep;93(3):256-64. doi: 10.1016/j.exer.2011.02.015. Epub 2011 Mar 3. PMID: 21376717.

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