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MedKoo Cat#: 585347 | Name: Unoprostone
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Description:

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

Unoprostone has an isopropyl ester (Rescula) that has been approved for ocular hypotension.

Chemical Structure

Unoprostone
Unoprostone
CAS#120373-36-6

Theoretical Analysis

MedKoo Cat#: 585347

Name: Unoprostone

CAS#: 120373-36-6

Chemical Formula: C22H38O5

Exact Mass: 382.2719

Molecular Weight: 382.54

Elemental Analysis: C, 69.08; H, 10.01; O, 20.91

Price and Availability

Size Price Availability Quantity
1mg USD 400.00
5mg USD 700.00
10mg USD 950.00
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Related CAS #
No Data
Synonym
Unoprostone
IUPAC/Chemical Name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid
InChi Key
TVHAZVBUYQMHBC-SNHXEXRGSA-N
InChi Code
InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1
SMILES Code
O=C(O)CCC/C=C\C[C@@H]1[C@@H](CCC(CCCCCCC)=O)[C@H](O)C[C@@H]1O
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
Shelf Life
>3 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 382.54 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: Yang TK, Kuo HT, Ju YJ, Chen CY, Chen WH, Wu AY, Lin CJ, Lee CC, Ho JH. Comparative analysis of medical treatments for long-term control of normal tension glaucoma: A systematic review and model-based network meta-analysis. Clin Exp Ophthalmol. 2024 Oct 9. doi: 10.1111/ceo.14447. Epub ahead of print. PMID: 39385332. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Unoprostone. 2022 Apr 18. PMID: 30000737. 3: Jedlowski PM, Jedlowski MF. Topical ophthalmic beta-blockers are associated with ocular pseudopemphigoid: A pharmacovigilance study of antiglaucoma medications utilising the FDA adverse event reporting system. Australas J Dermatol. 2022 May;63(2):222-227. doi: 10.1111/ajd.13828. Epub 2022 Mar 22. PMID: 35316535. 4: 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. 5: Lo KJ, Ko YC, Hwang DK, Liu CJ. The influence of topical non-steroidal anti- inflammatory drugs on the intraocular pressure lowering effect of topical prostaglandin analogues-A systemic review and meta-analysis. PLoS One. 2020 Sep 14;15(9):e0239233. doi: 10.1371/journal.pone.0239233. PMID: 32925955; PMCID: PMC7489511. 6: Heo JY, Ooi YH, Rhee DJ. Effect of prostaglandin analogs: Latanoprost, bimatoprost, and unoprostone on matrix metalloproteinases and their inhibitors in human trabecular meshwork endothelial cells. Exp Eye Res. 2020 May;194:108019. doi: 10.1016/j.exer.2020.108019. Epub 2020 Mar 25. PMID: 32222455; PMCID: PMC7262744. 7: Takagi Y, Santo K, Hashimoto M, Fukuchi T. Ocular hypotensive effects of prostaglandin analogs in Japanese patients with normal-tension glaucoma: a literature review. Clin Ophthalmol. 2018 Sep 21;12:1837-1844. doi: 10.2147/OPTH.S166657. PMID: 30275680; PMCID: PMC6158003. 8: Wei Y, Liao H, Ye J. Therapeutic effects of various therapeutic strategies on non-exudative age-related macular degeneration: A PRISMA-compliant network meta- analysis of randomized controlled trials. Medicine (Baltimore). 2018 May;97(21):e10422. doi: 10.1097/MD.0000000000010422. PMID: 29794727; PMCID: PMC6393096. 9: Klimko PG, Sharif NA. Discovery, characterization and clinical utility of prostaglandin agonists for the treatment of glaucoma. Br J Pharmacol. 2019 Apr;176(8):1051-1058. doi: 10.1111/bph.14327. Epub 2018 May 17. PMID: 29665040; PMCID: PMC6451111. 10: Nagai N, Yamada S, Kawasaki J, Koyanagi E, Saijo S, Kaji H, Nishizawa M, Nakazawa T, Abe T. Pharmacokinetic and Safety Evaluation of a Transscleral Sustained Unoprostone Release Device in Monkey Eyes. Invest Ophthalmol Vis Sci. 2018 Feb 1;59(2):644-652. doi: 10.1167/iovs.17-22429. PMID: 29392308. 11: Takemoto D, Higashide T, Saito Y, Ohkubo S, Udagawa S, Takeda H, Sugiyama K. Intraocular pressure and visual field changes in normal-tension glaucoma patients treated using either unoprostone or latanoprost: a prospective comparative study. Clin Ophthalmol. 2017 Sep 1;11:1617-1624. doi: 10.2147/OPTH.S144344. PMID: 28979091; PMCID: PMC5589109. 12: Nagai N, Izumida Y, Yamazaki Y, Kaji H, Kawasaki J, Nishizawa M, Abe T. Physicochemical and biological characterization of sustained isopropyl unoprostone-release device made of poly(ethyleneglycol) dimethacrylates. J Mater Sci Mater Med. 2017 Jul;28(7):107. doi: 10.1007/s10856-017-5919-2. Epub 2017 May 22. PMID: 28534288. 13: Shiragami C, Miyake M, Fujiwara A, Morizane Y, Tsujikawa A, Yamashita A, Shiraga F. Effect of topical isopropyl unoprostone on macular atrophy progression in eyes with exudative age-related macular degeneration. Medicine (Baltimore). 2017 Mar;96(12):e6422. doi: 10.1097/MD.0000000000006422. PMID: 28328847; PMCID: PMC5371484. 14: Nagai N, Koyanagi E, Izumida Y, Liu J, Katsuyama A, Kaji H, Nishizawa M, Osumi N, Kondo M, Terasaki H, Mashima Y, Nakazawa T, Abe T. Long-Term Protection of Genetically Ablated Rabbit Retinal Degeneration by Sustained Transscleral Unoprostone Delivery. Invest Ophthalmol Vis Sci. 2016 Dec 1;57(15):6527-6538. doi: 10.1167/iovs.16-20453. PMID: 27918826. 15: Nagai N, Iwata S, Kaji H, Sampei K, Katsukura Y, Onami H, Nishizawa M, Nakazawa T, Mashima Y, Abe T. Protective effects of sustained transscleral unoprostone delivery against retinal degeneration in S334ter rhodopsin mutant rats. J Biomed Mater Res B Appl Biomater. 2016 Nov;104(8):1730-1737. doi: 10.1002/jbm.b.33522. Epub 2015 Sep 10. PMID: 27753245. 16: Li T, Lindsley K, Rouse B, Hong H, Shi Q, Friedman DS, Wormald R, Dickersin K. Comparative Effectiveness of First-Line Medications for Primary Open-Angle Glaucoma: A Systematic Review and Network Meta-analysis. Ophthalmology. 2016 Jan;123(1):129-40. doi: 10.1016/j.ophtha.2015.09.005. Epub 2015 Oct 31. PMID: 26526633; PMCID: PMC4695285. 17: Yu L, Eaton AF, Yue Q, Bao HF, Ma HP, Cuppoletti J, Eaton DC. Unoprostone activation of BK (KCa1.1) channel splice variants. Biochim Biophys Acta. 2015 Nov;1848(11 Pt A):2859-67. doi: 10.1016/j.bbamem.2015.08.005. Epub 2015 Aug 13. PMID: 26277265; PMCID: PMC4598293. 18: Tanano I, Nagaoka T, Ono S, Omae T, Otani S, Yoshida A. Vasodilatory mechanisms of unoprostone isopropyl in isolated porcine retinal arterioles. Mol Vis. 2015 Jun 12;21:699-705. PMID: 26120274; PMCID: PMC4463970. 19: Akiyama M, Ikeda Y, Yoshida N, Notomi S, Murakami Y, Hisatomi T, Enaida H, Ishibashi T. Therapeutic efficacy of topical unoprostone isopropyl in retinitis pigmentosa. Acta Ophthalmol. 2014 May;92(3):e229-34. doi: 10.1111/aos.12293. PMID: 24868583. 20: Nagai N, Kaji H, Onami H, Katsukura Y, Ishikawa Y, Nezhad ZK, Sampei K, Iwata S, Ito S, Nishizawa M, Nakazawa T, Osumi N, Mashima Y, Abe T. A platform for controlled dual-drug delivery to the retina: protective effects against light-induced retinal damage in rats. Adv Healthc Mater. 2014 Oct;3(10):1555-60, 1524. doi: 10.1002/adhm.201400114. Epub 2014 Apr 19. PMID: 24753450.