Bimatoprost / AGN 192024
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Product Description
Bimatoprost is a synthetic prostaglandin analog primarily used as an ophthalmic agent for treating glaucoma and ocular hypertension by reducing intraocular pressure through increased aqueous humor outflow. Marketed under brand names such as Lumigan and Latisse, it is available in ophthalmic solution and implant forms. Its chemical structure features a prostamide backbone that differentiates it from natural prostaglandins. Bimatoprost is also used cosmetically to promote eyelash growth, making them longer, thicker, and darker. While effective, it can cause side effects like eye redness, itching, and changes in iris color. It should be used with caution in patients with intraocular inflammation.
Synthesis Methods
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Starting Material: Typically begins with a Corey Lactone.
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Key Steps:
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Stereoselective Reactions: Wittig reactions, hydroxylation, reductions to build carbon chains and introduce correct stereochemistry.
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Introduction of Ethylamide Group: Differentiates it from other prostaglandins like latanoprost.
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Uses
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Medical Uses:
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Ophthalmology: Used to treat open-angle glaucoma and ocular hypertension by reducing intraocular pressure (IOP).
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Cosmetic Use: Promotes eyelash growth, marketed under the brand name Latisse.
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Other Uses:
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Research: Studied for its effects on hair growth and potential use in treating other forms of alopecia.
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Veterinary Medicine: Used in veterinary formulations for similar indications as in humans.
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Mechanism of Action
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Prostaglandin Analog: Functions by stimulating prostaglandin FP receptors as an agonist.
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IOP Reduction: Increases aqueous humor outflow via the uveoscleral pathway, reducing intraocular pressure.
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Eyelash Growth: Promotes the transition from the telogen to anagen phase of the hair cycle, prolonging the anagen phase, and increasing melanogenesis.
Clinical Trials and Studies
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Efficacy in Glaucoma: Demonstrated significant reduction in intraocular pressure in multiple phase 3 clinical trials.
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Eyelash Hypotrichosis: Effective in promoting eyelash growth, with studies showing significant improvements in eyelash length, thickness, and pigmentation.
Additional Information
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Brand Names: Lumigan, Latisse, Durysta.
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Generic Formulations: Widely available.
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Research: Ongoing studies exploring its use in other conditions and potential long-term effects.
Chemical Properties
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Molecular Formula: C₂₅H₃₇NO₄
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Molecular Weight: 415.6 g/mol
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CAS Number: 155206-00-1
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IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
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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
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InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N
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SMILES: CCNC(=O)CCC/C=C\C[C@H]1C@HO
Physical Properties
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Appearance: Typically a white to off-white powder in its pure form.
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Solubility: Freely soluble in ethanol, methanol, and acetonitrile; slightly soluble in water.
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Storage: Store at controlled room temperature, protected from light.
Safety and Toxicity
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Common Side Effects: Eye redness, itching, dryness, eyelash darkening, increased iris pigmentation, eyelid skin darkening, and growth of hair around the eyes.
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Contraindications: Hypersensitivity to bimatoprost or any component of the formulation.
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Warnings: Can cause permanent darkening of the iris and should be used with caution in patients with intraocular inflammation.
Regulatory and Classification
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FDA Approval: Approved for reducing intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
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ATC Code: S01EE03
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Pharmacological Classification: Prostaglandin Analog, Antiglaucoma Agent, Antihypertensive Agent.