Bimatoprost (AGN 192024)

Alias: AGN 192024; Bimatoprostum; AGN192024; Lumigan; AGN-192024; Latisse; Lumigan

Cat No.:V2071 Purity: ≥98%

COA Product Data Instructions for use SDS

Bimatoprost (AGN 192024) Chemical Structure CAS No.: 155206-00-1
Product category: Prostaglandin Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Bimatoprost (AGN 192024):

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

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Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Bimatoprost (AGN-192024; Latisse; Lumigan; Bimatoprostum; AGN192024) is a potent FP (Prostaglandin F) receptor agonist and a prostaglandin analog used topically as eye drops to control the progression of glaucoma and in the management of ocular hypertension. Bimatoprost has a mild aqueous humor flow stimulation rate of 14% at night and 13% during the day. Its ocular hypotensive action is primarily caused by a 26% reduction in tonographic resistance to outflow. Bimatoprost improves the outflow pathway that is sensitive to pressure. Bimatoprost, with a K(i) of 6.31 μM, displaces [3H]prostaglandin F(2alpha) from FP receptors. With EC(50) of 2.94 μM and 2.2 μM, bimatoprost rapidly mobilizes intracellular Ca(2+) via native FP receptors in 3T3 mouse fibroblasts and cloned human FP receptors expressed in human embryonic kidney cells.

Biological Activity I Assay Protocols (From Reference)

ln Vitro

In vitro activity: Bimatoprost has a mild aqueous humor flow stimulation rate of 14% at night and 13% during the day. Its ocular hypotensive action is primarily caused by a 26% reduction in tonographic resistance to outflow. Bimatoprost improves the outflow pathway that is sensitive to pressure. Prostaglandin F(2alpha) [³H] is displaced from FP receptors by bimatoprost, with a K(i) of 6.31 μM. With EC(50) of 2.94 μM and 2.2 μM, bimatoprost rapidly mobilizes intracellular Ca(2+) via native FP receptors in 3T3 mouse fibroblasts and cloned human FP receptors expressed in human embryonic kidney cells.[2] In the cat iris, bistoprost increases the expression of Cyr61 mRNA. The activation of a different receptor, rather than the prostaglandin FP receptor, is responsible for the up-regulation of Cyr61 mRNA expression that is induced by bimatoprost.[3] While prostaglandin F(2 alpha) and 17-phenyl prostaglandin F(2 alpha) elicit signaling responses in the same cells, bimatoprost consistently elicits responses in different cells within the same tissue preparation. In various cat iris sphincter cells, bistatoprost preferentially increases intracellular calcium signaling.[4]

ln Vivo

Bimatoprost is a powerful prostaglandin FP receptor agonist and the ethyl amide derivative of 17-phenyl trinor PGF2α. When bimatoprost is administered, [Ca2+] experiences an instantaneous, strong spike that quickly returns to baseline levels. At the FP prostanoid receptors in rats, mice, and humans, bimatoprost exhibits direct agonist activities. [5]

Animal Protocol

References

[1]. Surv Ophthalmol . 2001 May:45 Suppl 4:S347-51.

[2]. Eur J Pharmacol . 2001 Dec 7;432(2-3):211-3.

[3]. J Biol Chem . 2003 Jul 18;278(29):27267-77.

[4]. Exp Eye Res . 2005 Jan;80(1):135-45

[5]. J Pharmacol Exp Ther . 2003 Jan;304(1):238-45.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C25H37NO4

Molecular Weight

415.57

Exact Mass

415.27

Elemental Analysis

C, 72.26; H, 8.97; N, 3.37; O, 15.40

CAS #

155206-00-1

Related CAS #

5,6-trans-Bimatoprost; 1163135-95-2; Bimatoprost-d5; Bimatoprost methyl ester; 38315-47-8; N-Desethyl Bimatoprost; 155205-89-3; Bimatoprost-d4

Appearance

Solid powder

SMILES

CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O

InChi Key

AQOKCDNYWBIDND-FTOWTWDKSA-N

InChi Code

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

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

Synonyms

AGN 192024; Bimatoprostum; AGN192024; Lumigan; AGN-192024; Latisse; Lumigan

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 83~250 mg/mL (199.7~601.6 mM)

Water: <1 mg/mL

Ethanol: ~83 mg/mL (~199.7 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4063 mL	12.0317 mL	24.0633 mL
	5 mM	0.4813 mL	2.4063 mL	4.8127 mL
	10 mM	0.2406 mL	1.2032 mL	2.4063 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT03850782	Active Recruiting	Drug: Bimatoprost (SR)	Open-Angle Glaucoma Ocular Hypertension	AbbVie	February 28, 2019	Phase 3
NCT05397600	Active Recruiting	Drug: Bimatoprost Ophthalmic	Ocular Hypertension Glaucoma	Laboratoires Thea	June 22, 2022	Phase 3
NCT05335122	Active Recruiting	Drug: OTX-TIC low dose Travoprost Intracameral Implant Drug: OTX-TIC high dose Travoprost Intracameral Implant	Open Angle Glaucoma Ocular Hypertension	Ocular Therapeutix, Inc.	March 16, 2022	Phase 2
NCT02390284	Active Recruiting	Drug: Latanoprost Drug: Bimatoprost Drug: Travoprost Drug: Timolol Drug: Dorzolamide	Glaucoma	University of Miami	September 2015	Phase 3
NCT06122090	Recruiting	Drug: Bimatoprost Drug: Saline	Burn Scar Scars Scarring Cicatrix Burns Laser	Medstar Health Research Institute	July 18, 2023	Phase 2

Biological Data

Regulation of Cyr61 and CTGF mRNA expression in cat iris following PGF_2α, Butaprost, and Bimatoprost treatment. J Biol Chem . 2003 Jul 18;278(29):27267-77.
Differential regulation of CTGF and Cyr61 following PGF_2α, Bimatoprost, and Butaprost treatments. J Biol Chem . 2003 Jul 18;278(29):27267-77.
Effects of PGF_2α, Butaprost, and Bimatoprost (AGN 192024) on the CTGF promoter and Cyr61 promoter luciferase reporter activity. J Biol Chem . 2003 Jul 18;278(29):27267-77.