Bimatoprost

CAS# 155206-00-1

Bimatoprost

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Chemical structure

Bimatoprost

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Chemical Properties of Bimatoprost

Cas No. 155206-00-1 SDF Download SDF
PubChem ID 5311027 Appearance Powder
Formula C25H37NO4 M.Wt 415.57
Type of Compound N/A Storage Desiccate at -20°C
Synonyms AGN 192024
Solubility DMSO : ≥ 100 mg/mL (240.63 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
SMILES CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
Standard InChIKey AQOKCDNYWBIDND-FTOWTWDKSA-N
Standard InChI InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Bimatoprost

DescriptionBimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Target: Prostaglandin Receptor Bimatoprost is a prostaglandin analog/prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes. In December 2008, the indication to lengthen eyelashes was approved by the U.S. Food and Drug Administration (FDA) the cosmetic formulation of bimatoprost is sold as Latisse. In 2008-2011, at least three case series suggested that bimatoprost has the ability to reduce adipose (fat) tissue. Bimatoprost activates prostamide alpha F2 receptors found in the hair follicle to stimulate its growth rate. Research led by Professor Randall and the University of Bradford found that it may also offer a treatment for scalp hair regrowth in trials conducted on samples taken from men undergoing hair transplants. According to Allergan's package labeling, users of its Latisse cosmetic product didn't develop darker irises in clinical studies however, patients should be advised about the potential for increased brown iris pigmentation which is likely to be permanent.

References:
[1]. Park J, et al. Changes to upper eyelid orbital fat from use of topical bimatoprost, travoprost, and latanoprost. Jpn J Ophthalmol. 2011 Jan 55(1):22-7. [2]. Filippopoulos T, et al. Periorbital changes associated with topical bimatoprost. Ophthal Plast Reconstr Surg. 2008 Jul-Aug 24(4):302-7.

Bimatoprost Dilution Calculator

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Preparing Stock Solutions of Bimatoprost

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4063 mL 12.0317 mL 24.0633 mL 48.1267 mL 60.1583 mL
5 mM 0.4813 mL 2.4063 mL 4.8127 mL 9.6253 mL 12.0317 mL
10 mM 0.2406 mL 1.2032 mL 2.4063 mL 4.8127 mL 6.0158 mL
50 mM 0.0481 mL 0.2406 mL 0.4813 mL 0.9625 mL 1.2032 mL
100 mM 0.0241 mL 0.1203 mL 0.2406 mL 0.4813 mL 0.6016 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Bimatoprost

Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension.

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References on Bimatoprost

Bimatoprost-induced late-onset choroidal detachment after trabeculectomy: A case report and review of the literature.[Pubmed:28151873]

Medicine (Baltimore). 2017 Feb;96(5):e5927.

BACKGROUND: Choroidal detachment (CD) is often observed at an early period particularly after trabeculectomy and glaucoma drainage implant surgery. However, topical antiglaucoma eye drop-induced CD is a rare complication. Here, we report a case of topical Bimatoprost-induced late-onset CD after trabeculectomy and review the literature. CASE REPORT: A 74-year-old man who suffered from primary open-angle glaucoma underwent his initial trabeculectomy with mitomycin-C in the right eye. Before the surgery, his intraocular pressure (IOP) was 20 to 22 mm Hg with Bimatoprost 0.03%, dorzolamide 1%, and brimonidine 0.1% and his best corrected visual acuity (BCVA) was 0.9. The mean deviation in Humphrey Visual Field Analyzer (24-2 program) was -27.83 db. After successful trabeculectomy, IOPs were 11 to 16 mm Hg without any medication. Eight months after the surgery, we restarted Bimatoprost to further reduce the IOP in the right eye, which was 15 mm Hg. At a hospital visit 2 months later, he complained of blurred vision that had persisted for the past 1 month; his IOP had decreased to 9 mm Hg. His BCVA was 0.04 and 3 quadrant CD was found. We discontinued Bimatoprost and started him on betamethasone 0.1% 4 times per day. However, CD marginally changed after 1 week, with IOP at 7 mm Hg; thus, we performed scleral drainage for CD. After 3 weeks of drainage, CD completely disappeared. IOP increased to 16 mm Hg and BCVA was 0.7. However, 3 months after the drainage, IOP increased to 29 mm Hg, and needling revision was thus performed. After the surgery, IOP remained at 14 to 16 mm Hg without any glaucoma medication and CD recurrence. A review of the literature showed that various antiglaucoma medications induce CD, regardless of the preceding glaucoma surgery and that CD is usually resolved by withdrawing the medication and administering topical steroids. However, most previous studies have shown the recurrence of CD by rechallenging the same drug. CONCLUSION: In our case, topical Bimatoprost induced late-onset CD after trabeculectomy. Early scleral drainage may be a good option to quickly resolve drug-induced CD and prevent its recurrence. Therefore, it must be kept in mind that various antiglaucoma medications induce CD.

Effects of LATISSE (bimatoprost 0.03 per cent topical solution) on the ocular surface.[Pubmed:28122407]

Clin Exp Optom. 2017 Nov;100(6):583-589.

PURPOSE: LATISSE is marketed for the treatment of hypotrichosis (loss of eyelashes), using a prostamide analogue and preserved with benzalkonium chloride, which is an effective preservative; however, it also causes irritation to the ocular surface. LATISSE is applied to the lid margin; however, with the blink, some solution may fall onto the ocular surface. The objective of this study was to assess the effects of LATISSE on the ocular surface over two months. METHODS: Non-dry eye participants interested in eyelash lengthening were invited to a prospective uncontrolled, open-label clinical study using LATISSE for two months. Eyelash length, subjective symptoms, tear film stability, osmolarity, ocular redness and intraocular pressure were evaluated at baseline (T0) and at one (T1) and two months (T2). RESULTS: Twenty-eight women (ages 18 to 29) entered the study. Fifteen completed the study with five who discontinued due to burning upon instillation and eight were lost to follow-up. Average eyelash length increased at each time (p < 0.001). Dryness, burning and grittiness remained low (less than 25/100) throughout the trial with dryness showing a significant change between T0 and T1 (p = 0.04), but not between T1 and T2 (p > 0.05). No difference (p > 0.05) was noted for the non-invasive break-up time, photochromametry or tear osmolarity. Intraocular pressure showed a decrease with time but translated to only a one to two mmHg change, which was not clinically relevant. CONCLUSIONS: LATISSE increases eyelash length within a short time (less than two months). Patients seeking eyelash enhancement options should be educated as to the use, precautions and any secondary effects, including the potential for discomfort upon instillation.

In Vivo Effects of Retrobulbar Bimatoprost Injection on Orbital Fat.[Pubmed:28369019]

Ophthalmic Plast Reconstr Surg. 2018 May/Jun;34(3):201-204.

PURPOSE: Recent publications have reported the adverse effects of prostaglandin analogues on the periocular tissues. These medications may cause periorbital lipodystrophy, enophthalmos, and deepening of the superior sulcus deformity. While these effects may have adverse consequences for some patients, the atrophy of the periorbital fat may have a useful role in diseases that lead to orbital and periorbital fat hypertrophy such as thyroid eye disease. In this pilot study, the authors investigated the effects of retrobulbar Bimatoprost injection on the intraocular pressure and orbital fat in a rat animal model. METHODS: Three rats were sedated and intraocular pressure was measured. A 0.1 ml aliquot of Bimatoprost was injected into the right orbit of all rats. In the left orbit, 0.1 ml of phosphate-buffered saline was injected as a control. Three weeks later, all rats were sedated and intraocular pressure was measured before euthanizing. Routine histologic staining was performed and thin sections through the intraconal orbital fat were obtained. Density of intraconal adipocytes was measured and adipocyte heterogeneity was determined using a computer image analysis algorithm. RESULTS: The specimens injected with Bimatoprost demonstrated atrophy of orbital fat with significantly increased adipocyte density (p = 0.009) and heterogeneity (p = 0.008) when compared with control. Intraocular pressure was not significantly decreased at 3 weeks after injection of retrobulbar Bimatoprost. CONCLUSIONS: In this pilot study, orbital injection of Bimatoprost demonstrated atrophy of intraconal adipocytes when compared with control orbits injected with saline. The orbits injected with Bimatoprost were noted to have smaller, more heterogeneous adipocytes that were densely packed in the intraconal space. The study limitations include the small sample size, which limited the ability for us to make conclusions about the effect on intraocular pressure. Nevertheless, the findings presented suggest that retrobulbar Bimatoprost may present a nonsurgical alternative to induce atrophy of the orbital fat without inducing inflammation or hypotony.

Bimatoprost for the treatment of eyelash, eyebrow and scalp alopecia.[Pubmed:28264599]

Expert Opin Investig Drugs. 2017 Apr;26(4):515-522.

INTRODUCTION: Alopecia is a common condition observed among people of all ages. It is a disorder that can involve only the scalp as observed in androgenetic alopecia or scalp and body as in alopecia areata or patients under chemotherapy treatment. There are several treatment options with different safety and efficacy outcomes. Bimatoprost, a synthetic prostamide F2alpha analog originally approved for the treatment of ocular hypertension and open-angle glaucoma, is now FDA approved as a 0.03%, solution to be applied once daily to increase eyelashes growth. Areas covered: In this review, the authors evaluate the role of Bimatoprost in idiopathic hypotrichosis of the eyelashes, in hypotrichosis of the eyelashes associated to chemotherapy, in alopecia areata of the eyelashes and eyebrows and in androgenetic alopecia. In addition, pharmacokinetics, pharmacodynamics, safety and tolerability of Bimatoprost are discussed. Expert opinion: Bimatoprost will likely be the third FDA approved weapon in the fight against hair loss. Prostaglandin analogs are the only possible treatment for hypotrichosis and alopecia of the eyelashes regardless of its etiology. Eyebrow hypotrichosis due to alopecia areata or frontal fibrosis alopecia can also possibly benefit of these medications.

Description

Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension.

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