General
Preferred name
BIMATOPROST
Synonyms
AGN 192024 ()
Bimatoprost (Lumigan) ()
bimatoprost sustained release, Allergan ()
Durysta ()
Prostamide ()
Latisse ()
Lumigan ()
AGN-192024 ()
17-phenyl trinor Prostaglandin F2.alpha. ethyl amide-d4 ()
P&D ID
PD009654
CAS
155206-00-1
Tags
prodrug
natural product
drug
available
Approved by
EMA
FDA
First approval
2001
Drug Status
investigational
approved
Drug indication
Alopecia
Glaucoma/ocular hypertension
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE
The elimination half-life of bimatoprost is approximately 45 minutes.[L6877,L6892]
MOA
Bimatoprost imitates the effects of prostamides, specifically prostaglandin F2α.[L6892] Bimatoprost mildly stimulates aqueous humor outflow, relieving elevated intraocular pressure and decreasing the risk of optic nerve damage. It is thought that bimatoprost reduces intraocular pressure (IOP) in humans by causing an increase in outflow of the aqueous humor via the trabecular meshwork and uveoscleral pathways.[L6877] It achieves the above effects by decreasing tonographic resistance to aqueous humor outflow.[A1367] Bimatoprost does not affect aqueous humor production.[A416]
INDICATION
Bimatoprost is used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.; These patients must be intolerant to other intraocular pressure lowering medications or inadequately responsive to other treatments.[L6877]; ; Bimatoprost is also indicated to treat eyelash hypotrichosis.[L6910]
ROE
One pharmacokinetic study of bimatoprost in 6 healthy volunteers determined that 67% of the administered dose was found to be excreted in the urine while 25% of the dose was recovered in the feces.[L6877]
TOXICITY
Oral LD50 in the rat is 980 mg/kg.[L6889]; No information is available at this time regarding bimatoprost overdose in humans. Provide supportive symptomatic treatment if an overdose occurs.[L6877]
METABOLISM
Bimatoprost is hydrolyzed to its active form, bimatoprost acid, in the eye.[L6913] Bimatoprost undergoes oxidation, N-deethylation, and glucuronidation after it is systemically absorbed, and this leads to the production of various metabolites.[L6877] In vitro studies show that CYP3A4 is an enzyme that participates in the metabolism of bimatoprost. Despite this, many enzymes and pathways metabolize bimatoprost, therefore, no significant drug-drug interactions are likely to occur.[L6892] Glucuronidated metabolites comprise most of the excreted drug product in the blood, urine, and feces in rats.[L6892]
DESCRIPTION
Bimatoprost is a prostaglandin analogue which binds to the prostanoid FP receptor. It has been demonstrated that bimatoprost is also a prodrug that is metabolised in vivo to its free acid form .
(GtoPdb)
PHARMACODYNAMICS
High intraocular pressure is a major risk factor for glaucoma-related visual field loss. A linear relationship exists between intraocular pressure and the risk of damaging the optic nerve, which can lead to considerable visual impairment.[L6877] Therefore, conditions such as ocular hypertension and glaucoma can cause dangerous elevations of intraocular pressure. Bimatoprost rapidly decreases intraocular pressure and reduces the risk for visual field loss from ocular hypertension due to various causes.[L6877]; ; Other effects of this drug may include gradual changes in eyelid pigmentation, changes in iris pigmentation, changes in eyelash pigmentation, growth and thickness.[L6877] Patients should be informed of these possible effects, especially if this drug is only administered to one eye, which may noticeably change in appearance with bimatoprost treatment.[L6877]
ABSORPTION
This drug is absorbed systemically when administered to the eye. A study was performed on 15 healthy volunteers and bimatoprost ophthalmic solution 0.03% was administered once daily for 14 days. The mean Cmax was approximately 0.08 ng/mL and AUC0-24hr was approximately 0.09 on days 7 and 14 of the study.[L6877] By 10 minutes, peak blood concentration was achieved. Bimatoprost was not detectable at 1.5 hours after administration in most subjects. The maximum blood concentration in a study of 6 healthy volunteers was determined to be 12.2 ng/mL. Steady state was reached in the first week of dosing.[L6877]; ; One drug label mentions that onset of decreased intraocular pressure occurs approximately 4 hours after the first administration and the peak effect occurs in the range of 8-12 hours. Bimatoprost effects may last up to 24 hours.[L6898]
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
18
AdooQ Bioactive Compound Library
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
48
Molecular Weight
415.27
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
4
Rotatable Bonds
12
Ring Count
2
Aromatic Ring Count
1
cLogP
3.15
TPSA
89.79
Fraction CSP3
0.56
Chiral centers
5.0
Largest ring
6.0
QED
0.31
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Target
PGF2
PGE2
AKR1C3, PTGER1, PTGER3, PTGFR
Prostaglandin Receptor
Indication
intraocular pressure, glaucoma, ocular hypertension
MOA
prostanoid receptor agonist
Source data
