Chemical Property of CID 127909
Chemical Property:
- Appearance/Colour:crystalline solid
- Vapor Pressure:9.94E-17mmHg at 25°C
- Melting Point:66-68°C
- Refractive Index:1.591
- Boiling Point:629.8 ºC at 760 mmHg
- PKA:14.25±0.20(Predicted)
- Flash Point:334.7 ºC
- PSA：89.79000
- Density:1.145 g/cm3
- LogP:3.53780
- Storage Temp.:−20°C
- Solubility.:Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
- XLogP3:2.8
- Hydrogen Bond Donor Count:4
- Hydrogen Bond Acceptor Count:4
- Rotatable Bond Count:12
- Exact Mass:415.27225866
- Heavy Atom Count:30
- Complexity:541
- Purity/Quality:
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99% *data from raw suppliers
17-Phenyl-tri-norprostaglandin F2α-ethyl amide ≥95%, solid *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
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SDS file from LookChem
Useful:
- Canonical SMILES:CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
- Isomeric SMILES:CCNC(=O)CCCC=CC[C@H]1[C@H](C[C@H]([C@@H]1C=C[C@H](CCC2=CC=CC=C2)O)O)O
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Description
Bimatoprost was first introduced in the US and Brazil as Lumigan?, an ophthalmic
solution (0.03%) for the reduction of elevated intraocular pressure (IOP) in patients with
open-angle glaucoma or ocular hypertension, a proven risk of glaucomatous visual field
loss. Bitamoprost is a new agent belonging to the PGF2α analog class of prostamides
launched in this indication after latanoprost, the most efficaceous topical medication
currently available. This synthetic fatty acid amide can be prepared by esterification of 17-
phenyl-18,19,20-trinorprostaglandin F2α followed by ethylamidation. Bimatoprost, as related
prostamides, is devoid of typical activities associated with PGF2,, analogs; it exhibits a
unique pharmacological profile in contracting the feline iris sphincter with an EC50 of 34 nM
without interacting with any known prostanoid receptors. Thus it mimics the action of
endogenous prostamides on specific receptors that lower IOP by increasing aqueous
humor outflow through both pressure-insensitive and pressure-sensitive pathways without
reducing humor formation. In a 3-month controlled clinical trial of efficacy and safety in patients with elevated IOP, bimatoprost demonstrated lower mean intraocular pressures at
every time point throughout the study, as well as a good tolerance and systemic safety
profile compared to latanoprost.
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Uses
Antiglaucoma. Synthetic prostamide; structurally related to prostaglandin F2a. Bimatoprost is a prostaglandin analog 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. It ha Bimatoprost is an antiglaucoma agent. Bimatoprost is an synthetic prostamide; structurally related to prostaglandin F2α. 17-phenyl trinor Prostaglandin F2α ethyl amide (17-phenyl trinor PGF2α ethyl amide) is an F-series PG analog which has been approved for use as an ocular hypotensive drug. Investigations in our lab have shown that 17-phenyl trinor PGF2α ethyl amide is converted by an amidase enzymatic activity in the bovine and human cornea to yield the corresponding free acid, with a conversion rate of about 40 μg/g corneal tissue/24 hours. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity.[Cayman Chemical]
