Bimatoprost isopropyl ester | CAS#130273-87-9 | prostaglandin analog

MedKoo Cat#: 326672 | Name: Bimatoprost isopropyl ester

Description:

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

Bimatoprost isopropyl ester is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost.

Chemical Structure

Bimatoprost isopropyl ester

CAS#130273-87-9

Theoretical Analysis

MedKoo Cat#: 326672

Name: Bimatoprost isopropyl ester

CAS#: 130273-87-9

Chemical Formula: C26H38O5

Exact Mass: 430.2719

Molecular Weight: 430.59

Elemental Analysis: C, 72.53; H, 8.90; O, 18.58

Price and Availability

Size	Price	Availability
100mg	USD 1,450.00	2 Weeks
200mg	USD 2,250.00	2 Weeks
500mg	USD 3,850.00	2 Weeks

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Synonym

Bimatoprost isopropyl ester; 17-phenyl trinor PGF2α-iPr; 17-phenyl trinor PGF2α isopropyl ester.

IUPAC/Chemical Name

isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)hept-5-enoate

InChi Key

JGZRPRSJSQLFBO-FWPUOYPASA-N

InChi Code

InChI=1S/C26H38O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21-,22+,23+,24-,25+/m0/s1

SMILES Code

O[C@@H]1[C@H](C/C=C\CCCC(OC(C)C)=O)[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bimatoprost isopropyl ester is a prostaglandin analog that targets prostaglandin receptors.

In vitro activity:

Table 1 provides a comprehensive overview of all possible interactions for prostaglandin analogs and their corresponding free acid forms with various efflux pumps studied. It was observed that the cellular accumulation of bimatoprost significantly elevated in the presence of GF120918 in MDCK-MDR1 but not in MDCK-BCRP cells. Interestingly, latanoprost and travoprost did not exhibit any statistically significant increase in their cellular accumulation with GF120918 in both MDCK-MDR1 and -BCRP cells. All three prostaglandin analogs, bimatoprost, latanoprost, and travoprost, showed significant interactions with all the isoforms of MRP studied, that is, MRP1, MRP2, and MRP5. On the other hand, free acid forms of bimatoprost, latanoprost, and travoprost did not produce statistically significant interactions in MDCK-MDR1 and -BCRP cells. However, these compounds interacted significantly with all isoforms of MRP (MRP1, MRP2, and MRP5). Table 2 summarizes the substrate specificities of all the prostaglandin analogs and their free acid forms with respect to P-gp, MRP1, MRP2, MRP5, and BCRP efflux pumps. Reference: J Ocul Pharmacol Ther. 2009 Dec; 25(6): 487–498. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/

In vivo activity:

In this study, topical bimatoprost once daily for one month showed thicker epidermis than in control eyes, indicating stimulation of skin cellular proliferation around the eyelash, this, together with the electron micrograph which showed heavily keratinized Henle’s layer, indicate changes of active process of keratinization making the eyelash stronger and resistant to pulling out of the skin. Other studies reported eyelid tightening and shortening in the NZW rabbit especially after 6 months of bimatoprost use. Periocular skin pigmentation was also observed previously with bimatoprost but occurred after several months of use. Reference: Clin Ophthalmol. 2019; 13: 2421–2426. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6901034/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	69.67
	Ethanol	30.0	69.67
	PBS (pH 7.2)	1.0	2.32

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 430.59 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.

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. Hariharan S, Minocha M, Mishra GP, Pal D, Krishna R, Mitra AK. Interaction of ocular hypotensive agents (PGF2 alpha analogs-bimatoprost, latanoprost, and travoprost) with MDR efflux pumps on the rabbit cornea. J Ocul Pharmacol Ther. 2009 Dec;25(6):487-98. doi: 10.1089/jop.2009.0049. PMID: 20028257; PMCID: PMC3096535. 2. Khidhir KG, Woodward DF, Farjo NP, Farjo BK, Tang ES, Wang JW, Picksley SM, Randall VA. The prostamide-related glaucoma therapy, bimatoprost, offers a novel approach for treating scalp alopecias. FASEB J. 2013 Feb;27(2):557-67. doi: 10.1096/fj.12-218156. Epub 2012 Oct 26. PMID: 23104985; PMCID: PMC3545535. 3. Sayed KM, Mostafa EM, Mounir A, Abd Elhaliem NG, Alsmman AH. Analysis of Bimatoprost-Induced changes on Rabbits eyelash Follicle: Clinical and Electron microscopic study. Clin Ophthalmol. 2019 Dec 5;13:2421-2426. doi: 10.2147/OPTH.S229335. PMID: 31824136; PMCID: PMC6901034.

In vitro protocol:

In vivo protocol:

1. Khidhir KG, Woodward DF, Farjo NP, Farjo BK, Tang ES, Wang JW, Picksley SM, Randall VA. The prostamide-related glaucoma therapy, bimatoprost, offers a novel approach for treating scalp alopecias. FASEB J. 2013 Feb;27(2):557-67. doi: 10.1096/fj.12-218156. Epub 2012 Oct 26. PMID: 23104985; PMCID: PMC3545535. 2. Sayed KM, Mostafa EM, Mounir A, Abd Elhaliem NG, Alsmman AH. Analysis of Bimatoprost-Induced changes on Rabbits eyelash Follicle: Clinical and Electron microscopic study. Clin Ophthalmol. 2019 Dec 5;13:2421-2426. doi: 10.2147/OPTH.S229335. PMID: 31824136; PMCID: PMC6901034.

1: Johansson M, Fransson D, Rundlöf T, Huynh NH, Arvidsson T. A general analytical platform and strategy in search for illegal drugs. J Pharm Biomed Anal. 2014 Nov;100:215-29. doi: 10.1016/j.jpba.2014.07.026. Epub 2014 Aug 4. PubMed PMID: 25171485. 2: Inoue K, Shiokawa M, Higa R, Sugahara M, Soga T, Wakakura M, Tomita G. Adverse periocular reactions to five types of prostaglandin analogs. Eye (Lond). 2012 Nov;26(11):1465-72. doi: 10.1038/eye.2012.195. Epub 2012 Oct 5. PubMed PMID: 23037910; PubMed Central PMCID: PMC3496108. 3: Inoue K, Shiokawa M, Wakakura M, Tomita G. Deepening of the upper eyelid sulcus caused by 5 types of prostaglandin analogs. J Glaucoma. 2013 Oct-Nov;22(8):626-31. doi: 10.1097/IJG.0b013e31824d8d7c. PubMed PMID: 22936280. 4: Faulkner R, Sharif NA, Orr S, Sall K, Dubiner H, Whitson JT, Moster M, Craven ER, Curtis M, Pailliotet C, Martens K, Dahlin D. Aqueous humor concentrations of bimatoprost free acid, bimatoprost and travoprost free acid in cataract surgical patients administered multiple topical ocular doses of LUMIGAN or TRAVATAN. J Ocul Pharmacol Ther. 2010 Apr;26(2):147-56. doi: 10.1089/jop.2009.0098. PubMed PMID: 20307216. 5: Ooi YH, Oh DJ, Rhee DJ. Effect of bimatoprost, latanoprost, and unoprostone on matrix metalloproteinases and their inhibitors in human ciliary body smooth muscle cells. Invest Ophthalmol Vis Sci. 2009 Nov;50(11):5259-65. doi: 10.1167/iovs.08-3356. Epub 2009 May 14. PubMed PMID: 19443729. 6: Gabelt BT, Hennes EA, Bendel MA, Constant CE, Okka M, Kaufman PL. Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys. J Ocul Pharmacol Ther. 2009 Feb;25(1):1-8. doi: 10.1089/jop.2008.0089. PubMed PMID: 19232013; PubMed Central PMCID: PMC2815338. 7: Law SK. First-line treatment for elevated intraocular pressure (IOP) associated with open-angle glaucoma or ocular hypertension: focus on bimatoprost. Clin Ophthalmol. 2007 Sep;1(3):225-32. PubMed PMID: 19668476; PubMed Central PMCID: PMC2701126. 8: Li N, Chen XM, Zhou Y, Wei ML, Yao X. Travoprost compared with other prostaglandin analogues or timolol in patients with open-angle glaucoma or ocular hypertension: meta-analysis of randomized controlled trials. Clin Experiment Ophthalmol. 2006 Nov;34(8):755-64. PubMed PMID: 17073898. 9: Ota T, Aihara M, Narumiya S, Araie M. The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63. PubMed PMID: 16249494. 10: Bartoe JT, Davidson HJ, Horton MT, Jung Y, Brightman AH. The effects of bimatoprost and unoprostone isopropyl on the intraocular pressure of normal cats. Vet Ophthalmol. 2005 Jul-Aug;8(4):247-52. PubMed PMID: 16008704. 11: Arcieri ES, Santana A, Rocha FN, Guapo GL, Costa VP. Blood-aqueous barrier changes after the use of prostaglandin analogues in patients with pseudophakia and aphakia: a 6-month randomized trial. Arch Ophthalmol. 2005 Feb;123(2):186-92. PubMed PMID: 15710814. 12: Wierzbowska J, Stankiewicz A. [Theoretical and clinical aspects of the use of prostaglandins in glaucoma therapy]. Klin Oczna. 2004;106(3):352-9. Review. Polish. PubMed PMID: 15515325. 13: Tomita G. [Recent changes in glaucoma management]. Nippon Ganka Gakkai Zasshi. 2004 Apr;108(4):191-2. Japanese. PubMed PMID: 15148733. 14: Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX. Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. PubMed PMID: 14733708. 15: Sharif NA, Kelly CR, Crider JY. Human trabecular meshwork cell responses induced by bimatoprost, travoprost, unoprostone, and other FP prostaglandin receptor agonist analogues. Invest Ophthalmol Vis Sci. 2003 Feb;44(2):715-21. PubMed PMID: 12556403. 16: Kelly CR, Williams GW, Sharif NA. Real-time intracellular Ca2+ mobilization by travoprost acid, bimatoprost, unoprostone, and other analogs via endogenous mouse, rat, and cloned human FP prostaglandin receptors. J Pharmacol Exp Ther. 2003 Jan;304(1):238-45. PubMed PMID: 12490597. 17: Phelan P. Reappraising first-line treatment in glaucoma management. Hosp Med. 2002 Sep;63(9):540-5. Review. PubMed PMID: 12357857. 18: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2002 Jul-Aug;24(6):371-91. PubMed PMID: 12224444. 19: Sharif NA, Kelly CR, Crider JY. Agonist activity of bimatoprost, travoprost, latanoprost, unoprostone isopropyl ester and other prostaglandin analogs at the cloned human ciliary body FP prostaglandin receptor. J Ocul Pharmacol Ther. 2002 Aug;18(4):313-24. PubMed PMID: 12222762. 20: Stjernschantz JW, Albert DM, Hu DN, Drago F, Wistrand PJ. Mechanism and clinical significance of prostaglandin-induced iris pigmentation. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S162-75. Review. PubMed PMID: 12204714.