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

MedKoo CAT#: 461232

CAS#: 120373-24-2

Description: Unoprostone isopropyl is a prostanoid and synthetic docosanoid approved for the treatment of open-angle glaucoma and ocular hypertension.

Chemical Structure

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Unoprostone isopropyl
CAS# 120373-24-2
Instruction

Theoretical Analysis

MedKoo Cat#: 461232
Name: Unoprostone isopropyl
CAS#: 120373-24-2
Chemical Formula: C25H44O5
Exact Mass: 424.32
Molecular Weight: 424.620
Elemental Analysis: C, 70.72; H, 10.45; O, 18.84

Price and Availability

Size Price Availability Quantity
5mg USD 400
10mg USD 680
50mg USD 1990
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Synonym: Unoprostone isopropyl; Rescula; UF 021; UF-021; UF021;

IUPAC/Chemical Name: isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate

InChi Key: XXUPXHKCPIKWLR-JHUOEJJVSA-N

InChi Code: InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1

SMILES Code: O=C(OC(C)C)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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 424.62 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:
In vitro protocol:
In vivo protocol:

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1: 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. PubMed PMID: 24868583.

2: 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. eCollection 2015. PubMed PMID: 26120274; PubMed Central PMCID: PMC4463970.

3: Harms NV, Toris CB. Current status of unoprostone for the management of glaucoma and the future of its use in the treatment of retinal disease. Expert Opin Pharmacother. 2013 Jan;14(1):105-13. doi: 10.1517/14656566.2013.748038. Epub 2012 Nov 30. Review. PubMed PMID: 23199345.

4: Cuppoletti J, Malinowska DH, Tewari KP, Chakrabarti J, Ueno R. Unoprostone isopropyl and metabolite M1 activate BK channels and prevent ET-1-induced [Ca²⁺]i increases in human trabecular meshwork and smooth muscle. Invest Ophthalmol Vis Sci. 2012 Aug 7;53(9):5178-89. doi: 10.1167/iovs.11-9046. PubMed PMID: 22786902.

5: Gunawardena KA, Crame N, Mertz B, Shams N. Safety of unoprostone isopropyl 0.15% ophthalmic solution in patients with mild to moderate asthma. Ophthalmologica. 2003 Mar-Apr;217(2):129-36. PubMed PMID: 12592052.

6: Sagawa H, Terasaki H, Nakanishi K, Tokita Y, Watanabe M. Regeneration of optic nerve fibers with unoprostone, a prostaglandin-related antiglaucoma drug, in adult cats. Jpn J Ophthalmol. 2014 Jan;58(1):100-9. doi: 10.1007/s10384-013-0282-4. Epub 2013 Oct 16. PubMed PMID: 24129676.

7: Wong M, Marion R, Reed K, Wang Y. Sorption of unoprostone isopropyl to packaging materials. Int J Pharm. 2006 Jan 13;307(2):163-7. Epub 2005 Nov 8. PubMed PMID: 16288842.

8: 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. PubMed PMID: 26277265; PubMed Central PMCID: PMC4598293.

9: Tawada A, Sugawara T, Ogata K, Hagiwara A, Yamamoto S. Improvement of central retinal sensitivity six months after topical isopropyl unoprostone in patients with retinitis pigmentosa. Indian J Ophthalmol. 2013 Mar;61(3):95-9. doi: 10.4103/0301-4738.109377. PubMed PMID: 23514642; PubMed Central PMCID: PMC3665054.

10: Yamamoto S, Sugawara T, Murakami A, Nakazawa M, Nao-I N, Machida S, Wada Y, Mashima Y, Myake Y. Topical isopropyl unoprostone for retinitis pigmentosa: microperimetric results of the phase 2 clinical study. Ophthalmol Ther. 2012 Dec;1(1):5. doi: 10.1007/s40123-012-0005-9. Epub 2012 Sep 6. PubMed PMID: 25135585; PubMed Central PMCID: PMC4108136.

11: Fung DS, Whitson JT. An evidence-based review of unoprostone isopropyl ophthalmic solution 0.15% for glaucoma: place in therapy. Clin Ophthalmol. 2014 Mar 10;8:543-54. doi: 10.2147/OPTH.S41562. eCollection 2014. Review. PubMed PMID: 24648719; PubMed Central PMCID: PMC3958522.

12: Makimoto Y, Sugiyama T, Kojima S, Azuma I. Long-term effect of topically applied isopropyl unoprostone on microcirculation in the human ocular fundus. Jpn J Ophthalmol. 2002 Jan-Feb;46(1):31-5. PubMed PMID: 11853711.

13: Yoshitomi T, Yamaji K, Ishikawa H, Ohnishi Y. Vasodilatory mechanism of unoprostone isopropyl on isolated rabbit ciliary artery. Curr Eye Res. 2004 Mar;28(3):167-74. PubMed PMID: 14977518.

14: Ofri R, Raz D, Kass PH, Lambrou GN, Percicot CL. The effect of 0.12% unoprostone isopropyl (rescula) on intraocular pressure in normotensive dogs. J Vet Med Sci. 2000 Dec;62(12):1313-5. PubMed PMID: 11193349.

15: Eisenberg DL, Camras CB. A preliminary risk-benefit assessment of latanoprost and unoprostone in open-angle glaucoma and ocular hypertension. Drug Saf. 1999 Jun;20(6):505-14. Review. PubMed PMID: 10392667.

16: Kashiwagi K, Tsukamoto K, Wakamatsu K, Itoh S, Suzuki M, Tsukahara S. Effects of isopropyl unoprostone on melanogenesis in mouse epidermal melanocytes. Jpn J Ophthalmol. 2001 May-Jun;45(3):259-63. PubMed PMID: 11369375.

17: Mukuno H, Nakamura M, Kanamori A, Nagai A, Negi A, Seigel G. Unoprostone isopropyl rescues retinal progenitor cells from apoptosis in vitro. Curr Eye Res. 2004 Dec;29(6):457-64. PubMed PMID: 15764090.

18: Bhattacherjee P, Paterson CA, Percicot C. Studies on receptor binding and signal transduction pathways of unoprostone isopropyl. J Ocul Pharmacol Ther. 2001 Oct;17(5):433-41. PubMed PMID: 11765148.

19: Yamamoto T, Kitazawa Y, Azuma I, Masuda K. Clinical evaluation of UF-021 (Rescula; isopropyl unoprostone). Surv Ophthalmol. 1997 Feb;41 Suppl 2:S99-103. PubMed PMID: 9154284.

20: Babiole M, Wilhelm F, Schoch C. In vitro corneal permeation of unoprostone isopropyl (UI) and its metabolism in the isolated pig eye. J Ocul Pharmacol Ther. 2001 Apr;17(2):159-72. PubMed PMID: 11324983.