Bimatoprost, a potent FP receptor agonist.

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

Product information

CAS Number: 155206-00-1

Molecular Weight: 415.57

Formula: C25H37NO4

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)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCC2C=CC=CC=2)[C@H](O)C[C@@H]1O

InChiKey: AQOKCDNYWBIDND-FTOWTWDKSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 36 mg/mL(86.62 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Bimatoprost mildly stimulates the rate of aqueous humor flow during the day (13%) and at night (14%), its ocular hypotensive action is due primarily to a 26% reduction in the tonographic resistance to outflow. Bimatoprost enhances the pressure-sensitive outflow pathway. Bimatoprost displaces [3H]prostaglandin F(2alpha) from FP receptors with K(i) of 6.31 μM. Bimatoprost rapidly mobilizes intracellular Ca(2+) via cloned human FP receptors expressed in human embryonic kidney cells and via native FP receptors in 3T3 mouse fibroblasts with EC(50) of 2.94 μM and 2.2 μM. Bimatoprost up-regulates Cyr61 mRNA expression in the cat iris. Bimatoprost-induced up-regulation of Cyr61 mRNA expression is not because of the activation of the prostaglandin FP receptor but a different receptor. Bimatoprost consistently evokes responses in different cells within the same tissue preparation, whereas prostaglandin F(2 alpha) and 17-phenyl prostaglandin F(2 alpha) elicites signaling responses in the same cells. Bimatoprost selectively stimulates intracellular calcium signaling in different cat iris sphincter cells.

In Vivo:

Bimatoprost is the ethyl amide derivative of 17-phenyl trinor PGF2α, a potent prostaglandin FP receptor agonist. Bimatoprost elicits an immediate, robust spike in [Ca2+] that rapidly decayes back to baseline levels. Bimatoprost possess direct agonist activities at the rat, mouse, and human FP prostanoid receptor.

References:

1. Liang Y, et al. J Biol Chem, 2003, 278(29), 27267-27277.
2. Sharif NA, et al. Eur J Pharmacol, 2001, 432(2-3), 211-213.
3. Brubaker RF, et al. Surv Ophthalmol, 2001, 45 Suppl 4, S347-351.

Products are for research use only. Not for human use.