Bimatoprost acid | CAS#38344-08-0 | PGF2α analog

MedKoo Cat#: 330161 | Name: Bimatoprost acid

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Description:

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

Bimatoprost acid is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor. It binds to the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α.

Chemical Structure

Bimatoprost acid

CAS#38344-08-0

Theoretical Analysis

MedKoo Cat#: 330161

Name: Bimatoprost acid

CAS#: 38344-08-0

Chemical Formula: C23H32O5

Exact Mass: 388.2250

Molecular Weight: 388.50

Elemental Analysis: C, 71.11; H, 8.30; O, 20.59

Price and Availability

Size	Price	Availability
5mg	USD 395.00	2 weeks
10mg	USD 750.00	2 weeks
25mg	USD 1,250.00	2 weeks

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Synonym

17-phenyl trinor Prostaglandin F2α; 17-phenyl trinor PGF2α; Bimatoprost acid; Bimatoprost (free acid);

IUPAC/Chemical Name

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

InChi Key

YFHHIZGZVLHBQZ-KDACTHKWSA-N

InChi Code

InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1

SMILES Code

O[C@@H]1[C@H](C/C=C\CCCC(O)=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

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C22M02C14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Bimatoprost acid 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 388.50 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: Kaluzhny Y, Kinuthia MW, Truong T, Lapointe AM, Hayden P, Klausner M. New Human Organotypic Corneal Tissue Model for Ophthalmic Drug Delivery Studies. Invest Ophthalmol Vis Sci. 2018 Jun 1;59(7):2880-2898. doi: 10.1167/iovs.18-23944. PubMed PMID: 30025134. 2: Klimko PG, Sharif NA. Discovery, characterization and clinical utility of prostaglandin agonists for the treatment of glaucoma. Br J Pharmacol. 2018 Apr 17. doi: 10.1111/bph.14327. [Epub ahead of print] Review. PubMed PMID: 29665040. 3: Shen J, Goodkin ML, Tong W, Attar M. Ocular pharmacokinetics and tolerability of bimatoprost ophthalmic solutions administered once or twice daily in rabbits, and clinical dosing implications. Clin Ophthalmol. 2017 Sep 28;11:1761-1767. doi: 10.2147/OPTH.S143428. eCollection 2017. Erratum in: Clin Ophthalmol. 2018 Aug 17;12:1471. PubMed PMID: 29026287; PubMed Central PMCID: PMC5627754. 4: Krupa M, Chodyński M, Ostaszewska A, Cmoch P, Dams I. A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost. Molecules. 2017 Jan 31;22(2). pii: E217. doi: 10.3390/molecules22020217. PubMed PMID: 28146132. 5: Gupta AK, Carviel J, Abramovits W. Treating Alopecia Areata: Current Practices Versus New Directions. Am J Clin Dermatol. 2017 Feb;18(1):67-75. doi: 10.1007/s40257-016-0230-4. Review. PubMed PMID: 27770310. 6: Narurkar VA, Cohen JL, Dayan S, Kaminer MS, Rivkin A, Shamban A, Sykes JM, Teller CF, Weinkle SH, Werschler WP, Drinkwater A, Pucci ML, Gallagher CJ. A Comprehensive Approach to Multimodal Facial Aesthetic Treatment: Injection Techniques and Treatment Characteristics From the HARMONY Study. Dermatol Surg. 2016 May;42 Suppl 2:S177-91. doi: 10.1097/DSS.0000000000000743. Erratum in: Dermatol Surg. 2016 Nov;42(11):1311. PubMed PMID: 27128246. 7: Doucette LP, Walter MA. Prostaglandins in the eye: Function, expression, and roles in glaucoma. Ophthalmic Genet. 2017 Mar-Apr;38(2):108-116. doi: 10.3109/13816810.2016.1164193. Epub 2016 Apr 12. Review. PubMed PMID: 27070211. 8: Yamada H, Yoneda M, Gosho M, Kato T, Zako M. Bimatoprost, latanoprost, and tafluprost induce differential expression of matrix metalloproteinases and tissue inhibitor of metalloproteinases. BMC Ophthalmol. 2016 Mar 8;16:26. doi: 10.1186/s12886-016-0202-8. PubMed PMID: 26956170; PubMed Central PMCID: PMC4784282. 9: Impagnatiello F, Toris CB, Batugo M, Prasanna G, Borghi V, Bastia E, Ongini E, Krauss AH. Intraocular Pressure-Lowering Activity of NCX 470, a Novel Nitric Oxide-Donating Bimatoprost in Preclinical Models. Invest Ophthalmol Vis Sci. 2015 Oct;56(11):6558-64. doi: 10.1167/iovs.15-17190. PubMed PMID: 26457541. 10: Thomson L, Jain S. An unusual case of breathlessness in a patient with chronic myeloid leukaemia: Case Report. Breathe (Sheff). 2015 Jun;11(2):141-5. doi: 10.1183/20734735.016514. PubMed PMID: 26306114; PubMed Central PMCID: PMC4487374. 11: Shin JA, Kim NW, Kang SS, Kim ML, Sung KR. In vitro Effects of Prostaglandin Analogs on Cultured Astrocytes Obtained from the Lamina Cribrosa. Curr Eye Res. 2016 May;41(5):676-82. doi: 10.3109/02713683.2015.1050741. Epub 2015 Aug 3. PubMed PMID: 26237412. 12: Urquhart P, Wang J, Woodward DF, Nicolaou A. Identification of prostamides, fatty acyl ethanolamines, and their biosynthetic precursors in rabbit cornea. J Lipid Res. 2015 Aug;56(8):1419-33. doi: 10.1194/jlr.M055772. Epub 2015 May 31. PubMed PMID: 26031663; PubMed Central PMCID: PMC4513984. 13: 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;100:215-229. doi: 10.1016/j.jpba.2014.07.026. Epub 2014 Aug 4. PubMed PMID: 25171485. 14: Franca JR, Foureaux G, Fuscaldi LL, Ribeiro TG, Rodrigues LB, Bravo R, Castilho RO, Yoshida MI, Cardoso VN, Fernandes SO, Cronemberger S, Ferreira AJ, Faraco AA. Bimatoprost-loaded ocular inserts as sustained release drug delivery systems for glaucoma treatment: in vitro and in vivo evaluation. PLoS One. 2014 Apr 30;9(4):e95461. doi: 10.1371/journal.pone.0095461. eCollection 2014. PubMed PMID: 24788066; PubMed Central PMCID: PMC4005758. 15: Taketani Y, Yamagishi R, Fujishiro T, Igarashi M, Sakata R, Aihara M. Activation of the prostanoid FP receptor inhibits adipogenesis leading to deepening of the upper eyelid sulcus in prostaglandin-associated periorbitopathy. Invest Ophthalmol Vis Sci. 2014 Mar 4;55(3):1269-76. doi: 10.1167/iovs.13-12589. PubMed PMID: 24508785. 16: Shafiee A, Bowman LM, Hou E, Hosseini K. Ocular pharmacokinetics of bimatoprost formulated in DuraSite compared to bimatoprost 0.03% ophthalmic solution in pigmented rabbit eyes. Clin Ophthalmol. 2013;7:1549-56. doi: 10.2147/OPTH.S48766. Epub 2013 Jul 31. PubMed PMID: 23940414; PubMed Central PMCID: PMC3737010. 17: Silvestri C, Martella A, Poloso NJ, Piscitelli F, Capasso R, Izzo A, Woodward DF, Di Marzo V. Anandamide-derived prostamide F2α negatively regulates adipogenesis. J Biol Chem. 2013 Aug 9;288(32):23307-21. doi: 10.1074/jbc.M113.489906. Epub 2013 Jun 25. PubMed PMID: 23801328; PubMed Central PMCID: PMC3743501. 18: Kenley RA, Filippone H, Giske M, Beidler D, Vehige J, Fleitman J. Equilibrium binding interactions between lotrafilcon a soft contact lenses and the two prostaglandin antiglaucoma drugs bimatoprost and tafluprost. Eye Contact Lens. 2013 Jul;39(4):295-302. doi: 10.1097/ICL.0b013e3182973d5c. PubMed PMID: 23771012. 19: Takano N, Tsuruma K, Ohno Y, Shimazawa M, Hara H. Bimatoprost protects retinal neuronal damage via Akt pathway. Eur J Pharmacol. 2013 Feb 28;702(1-3):56-61. doi: 10.1016/j.ejphar.2013.01.038. Epub 2013 Feb 6. PubMed PMID: 23395963. 20: Nicotra LL, Vu M, Harvey BS, Smid SD. Prostaglandin ethanolamides attenuate damage in a human explant colitis model. Prostaglandins Other Lipid Mediat. 2013 Jan;100-101:22-9. doi: 10.1016/j.prostaglandins.2013.01.003. Epub 2013 Feb 1. PubMed PMID: 23380599.