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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H37NO4
Molecular Weight 415.5656
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BIMATOPROST

SMILES

CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC2=CC=CC=C2

InChI

InChIKey=AQOKCDNYWBIDND-FTOWTWDKSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H37NO4
Molecular Weight 415.5656
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Bimatoprost (marketed in the US, Canada and Europe by Allergan, under the trade name Lumigan) ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. It binds to the prostanoid FP receptor. It selectively mimics the effects of naturally occurring substances, prostamides. Bimatoprost is believed to lower intraocular pressure (IOP) in humans by increasing outflow of aqueous humor through both the trabecular meshwork and uveoscleral routes. Elevated IOP presents a major risk factor for glaucomatous field loss. The higher the level of IOP, the greater the likelihood of optic nerve damage and visual field loss. Bimatoprost is the major circulating species in the blood once it reaches the systemic circulation following ocular dosing. Bimatoprost then undergoes oxidation, N-deethylation and glucuronidation to form a diverse variety of metabolites. In human blood, bimatoprost resides mainly in the plasma. Approximately 12% of bimatoprost remains unbound in human plasma.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
681.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LUMIGAN
Primary
LUMIGAN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.08 ng/mL
1 drop 1 times / day steady-state, topical
BIMATOPROST plasma
Homo sapiens
12.2 ng/mL
3.12 μg/kg bw single, intravenous
BIMATOPROST plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.09 ng × h/mL
1 drop 1 times / day steady-state, topical
BIMATOPROST plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
45 min
3.12 μg/kg bw single, intravenous
BIMATOPROST plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
1 drop 1 times / day steady-state, topical
BIMATOPROST plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
One drop in the affected eye(s) once daily in the evening
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
QXS94885MZ
Record Status Validated (UNII)
Record Version