Bimatoprost
[CAS# 155206-00-1]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Bimatoprost
• Synonyms: (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
• Molecular Formula: C₂₅H₃₇NO₄
• Molecular Weight: 415.57
• CAS Registry Number: 155206-00-1
• EC Number: 642-890-9
• SMILES: CCNC(=O)CCC/C=CC[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O

Properties

• Solubility: 0.9948 mg/L (25 °C water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.591, Calc.^*
• Melting point: 267.01 °C
• Boiling Point: 629.8±55.0 °C (760 mmHg), Calc.^*, 616.48 °C
• Flash Point: 334.7±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H319-H340-H360-H361
• Safety Statements: P203-P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P317-P318-P321-P330-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360
Germ cell mutagenicity	Muta.	1B	H340
Acute toxicity	Acute Tox.	4	H312
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	1A	H360
Reproductive toxicity	Lact.	-	H362
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Bimatoprost, also known as Lumigan, was discovered and developed by the pharmaceutical company Allergan. It was initially studied as an ocular hypotensive agent to reduce intraocular pressure (IOP) in patients with glaucoma and ocular hypertension. Bimatoprost belongs to a class of drugs called prostaglandin analogs, which mimic the effects of prostaglandins produced naturally in the body.

Prostaglandins play an important role in regulating various physiological processes including intraocular pressure, inflammation, and smooth muscle contraction. Bimatoprost is mainly used to treat open-angle glaucoma and ocular hypertension. Bimatoprost works by increasing the outflow of aqueous humor (the fluid inside the eye), thereby lowering intraocular pressure and reducing the risk of optic nerve damage. Regulators also approved bimatoprost for the treatment of hypotrichosis, a condition characterized by insufficient or sparse eyelash growth. Bimatoprost promotes eyelash growth, increases eyelash length, thickness and darkness, and enhances the overall appearance of eyelashes. The exact mechanism of action of bimatoprost on eyelash growth is not fully understood, but it is believed to stimulate the anagen (anagen) phase of the eyelash hair cycle. Bimatoprost is commonly used for cosmetic purposes, particularly to enhance eyelash length, fullness and darkness. It is often prescribed or recommended by dermatologists and cosmetic surgeons as a non-invasive alternative to eyelash extensions, mascara and false eyelashes. Bimatoprost also has potential application in the treatment of androgenetic alopecia (male and female pattern hair loss). Preliminary research suggests that bimatoprost can stimulate hair growth and improve hair density when applied topically to the scalp. In addition to its current clinical indications, bimatoprost remains the subject of ongoing research and development for potential new therapeutic applications. Bimatoprost's diverse pharmacological properties and favorable safety profile make it a promising candidate for future therapeutic innovation.

References

2003. Ocular Hypotensive FP Prostaglandin (PG) Analogs: PG Receptor Subtype Binding Affinities and Selectivities, and Agonist Potencies at FP and Other PG Receptors in Cultured Cells. Journal of ocular pharmacology and therapeutics, 19, 6.
DOI: 10.1089/108076803322660422

2019. New insights into the pathogenesis and nonsurgical management of Graves orbitopathy. Nature reviews. Endocrinology, 16, 2.
DOI: 10.1038/s41574-019-0305-4

2024. Medical Therapy of Childhood Glaucoma. Childhood Glaucoma, 15.
DOI: 10.1007/978-3-031-61073-8_15