Bimatoprost isopropyl ester
CAS No:
130209-76-6
Molecular Formula：
C26H38O5
Molecular Weight：
430.58
Storage:
Store in a tightly closed container in a cool, dry，Protect from moisture and direct sunlight.
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Technical Data
| Appearance | pale yellow to colorless solid |
|---|---|
| Identification | HNMR HPLC |
| Solubility | Practically insoluble in water, freely soluble in |
| Water | ≤0.5% |
| Related substances | Individual impurity：≤0.5 % |
| Residual Solvent | Ethanol： ≤ 0.5 % |
| Purity | ≥ 98.0% |
Description
Bimatoprost isopropyl ester (17-phenyl trinor PGF₂α isopropyl ester) is a synthetic prostaglandin F‑series analog. It is the isopropyl ester prodrug of bimatoprost, and its active form—the free acid 17‑phenyl trinor PGF₂α—is a potent FP receptor agonist. It should be noted that its C‑15 stereoisomer, 15(R)‑bimatoprost isopropyl ester, is a related isomer and potential impurity of latanoprost.
The IC50 values for the free acid forms of 15(S)-17-phenyl trinor PGF2α and 15(R)-17-phenyl trinor PGF2α were determined to be 0.71 nM and 30 nM, respectively, in a FP receptor binding assay using the cat iris sphincter muscle.1 A 3 μg dose of 15(R)-17-phenyl trinor PGF2α caused a 1.9 mmHg reduction of IOP in normotensive cynomolgus monkeys.
Safety Information
GHS
Pictogram:
Signal Word:
Danger
Hazard Statements:
H302+H312+H332 : Harmful if swallowed, in contact with skin or if inhaled
[Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H302 : Harmful if swallowed [Warning Acute toxicity, oral]
H312 : Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 : Harmful if inhaled [Warning Acute toxicity, inhalation]
H360 : May damage fertility or the unborn child [Danger Reproductive toxicity]
Precautionary Statements:
P203: Obtain, read and follow all safety instructions before use.
P261: Avoid breathing dust/fume/gas/mist/vapors/spray.
P264: Wash skin thoroughly after handling.
P270: Do not eat, drink or smoke when using this product.
P271: Use only outdoors or in a well-ventilated area.
P280: Wear protective gloves/protective clothing/eye protection/face protection.
P301+P317: IF SWALLOWED: Get medical help.
P302+P352: IF ON SKIN: Wash with plenty of water.
P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
P317: Get emergency medical help.
P318: If exposed or concerned, get medical advice.
P321: Specific treatment (see first aid measures on this label).
P330: Rinse mouth.
P362+P364: Take off contaminated clothing and wash it before reuse.
P405: Store locked up.
P501: Dispose of contents/container to an approved waste disposal plant.
References
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.
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