U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H37NO4
Molecular Weight 415.5665
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BIMATOPROST

SMILES

CCN=C(CCC/C(/[H])=C(/[H])\C[C@]1([H])[C@@]([H])(/C(/[H])=C(\[H])/[C@]([H])(CCc2ccccc2)O)[C@@]([H])(C[C@]1([H])O)O)O

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
681.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LUMIGAN

Approved Use

LUMIGAN® (bimatoprost ophthalmic solution) 0.01% is indicated for the reduction of elevated intraocular pressure in patients with open angle glaucoma or ocular hypertension.

Launch Date

1.28321284E12
Primary
LUMIGAN

Approved Use

LUMIGAN® (bimatoprost ophthalmic solution) 0.01% is indicated for the reduction of elevated intraocular pressure in patients with open angle glaucoma or ocular hypertension.

Launch Date

1.28321284E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.08 ng/mL
1 drop 1 times / day steady-state, topical
dose: 1 drop
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
BIMATOPROST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
12.2 ng/mL
3.12 μg/kg bw single, intravenous
dose: 3.12 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BIMATOPROST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.09 ng × h/mL
1 drop 1 times / day steady-state, topical
dose: 1 drop
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
BIMATOPROST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45 min
3.12 μg/kg bw single, intravenous
dose: 3.12 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BIMATOPROST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
1 drop 1 times / day steady-state, topical
dose: 1 drop
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
BIMATOPROST plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.3 mg/mL 1 times / day multiple, ophthalmic
Recommended
Dose: 0.3 mg/mL, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.3 mg/mL, 1 times / day
Sources: Page: p. 52
unhealthy, adult
n = 137
Health Status: unhealthy
Age Group: adult
Population Size: 137
Sources: Page: p. 52
Disc. AE: Eczema, Dry eye...
AEs leading to
discontinuation/dose reduction:
Eczema (1 patient)
Dry eye (1 patient)
Eye inflammation (1 patient)
Contact dermatitis (1 patient)
Sources: Page: p. 52
0.01 % 1 times / day multiple, ophthalmic
Dose: 0.01 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.01 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 186
Health Status: unhealthy
Age Group: adult
Population Size: 186
Sources: Page: p. 28
Disc. AE: Conjunctival hyperemia, Headache...
AEs leading to
discontinuation/dose reduction:
Conjunctival hyperemia (3 patients)
Headache (1 patient)
Blurred vision (1 patient)
Nausea (1 patient)
Sources: Page: p. 28
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
Disc. AE: Eye irritation, Eye pruritus...
AEs leading to
discontinuation/dose reduction:
Eye irritation (1 patient)
Eye pruritus (1 patient)
Ocular discomfort (1 patient)
Conjunctival hyperemia (1 patient)
Maculopathy (1 patient)
Sources: Page: p. 28
AEs

AEs

AESignificanceDosePopulation
Contact dermatitis 1 patient
Disc. AE
0.3 mg/mL 1 times / day multiple, ophthalmic
Recommended
Dose: 0.3 mg/mL, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.3 mg/mL, 1 times / day
Sources: Page: p. 52
unhealthy, adult
n = 137
Health Status: unhealthy
Age Group: adult
Population Size: 137
Sources: Page: p. 52
Dry eye 1 patient
Disc. AE
0.3 mg/mL 1 times / day multiple, ophthalmic
Recommended
Dose: 0.3 mg/mL, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.3 mg/mL, 1 times / day
Sources: Page: p. 52
unhealthy, adult
n = 137
Health Status: unhealthy
Age Group: adult
Population Size: 137
Sources: Page: p. 52
Eczema 1 patient
Disc. AE
0.3 mg/mL 1 times / day multiple, ophthalmic
Recommended
Dose: 0.3 mg/mL, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.3 mg/mL, 1 times / day
Sources: Page: p. 52
unhealthy, adult
n = 137
Health Status: unhealthy
Age Group: adult
Population Size: 137
Sources: Page: p. 52
Eye inflammation 1 patient
Disc. AE
0.3 mg/mL 1 times / day multiple, ophthalmic
Recommended
Dose: 0.3 mg/mL, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.3 mg/mL, 1 times / day
Sources: Page: p. 52
unhealthy, adult
n = 137
Health Status: unhealthy
Age Group: adult
Population Size: 137
Sources: Page: p. 52
Blurred vision 1 patient
Disc. AE
0.01 % 1 times / day multiple, ophthalmic
Dose: 0.01 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.01 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 186
Health Status: unhealthy
Age Group: adult
Population Size: 186
Sources: Page: p. 28
Headache 1 patient
Disc. AE
0.01 % 1 times / day multiple, ophthalmic
Dose: 0.01 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.01 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 186
Health Status: unhealthy
Age Group: adult
Population Size: 186
Sources: Page: p. 28
Nausea 1 patient
Disc. AE
0.01 % 1 times / day multiple, ophthalmic
Dose: 0.01 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.01 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 186
Health Status: unhealthy
Age Group: adult
Population Size: 186
Sources: Page: p. 28
Conjunctival hyperemia 3 patients
Disc. AE
0.01 % 1 times / day multiple, ophthalmic
Dose: 0.01 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.01 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 186
Health Status: unhealthy
Age Group: adult
Population Size: 186
Sources: Page: p. 28
Conjunctival hyperemia 1 patient
Disc. AE
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
Eye irritation 1 patient
Disc. AE
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
Eye pruritus 1 patient
Disc. AE
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
Maculopathy 1 patient
Disc. AE
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
Ocular discomfort 1 patient
Disc. AE
0.0125 % 1 times / day multiple, ophthalmic
Dose: 0.0125 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.0125 %, 1 times / day
Sources: Page: p. 28
unhealthy, adult
n = 188
Health Status: unhealthy
Age Group: adult
Population Size: 188
Sources: Page: p. 28
PubMed

PubMed

TitleDatePubMed
Comparison of the ocular hypotensive lipid AGN 192024 with timolol: dosing, efficacy, and safety evaluation of a novel compound for glaucoma management.
2001 Jul
Six-month comparison of bimatoprost once-daily and twice-daily with timolol twice-daily in patients with elevated intraocular pressure.
2001 May
Mechanism of action of bimatoprost (Lumigan).
2001 May
The pharmacology of bimatoprost (Lumigan).
2001 May
Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension.
2002
One-year, randomized study comparing bimatoprost and timolol in glaucoma and ocular hypertension.
2002 Oct
Hydrolysis of bimatoprost (Lumigan) to its free acid by ocular tissue in vitro.
2003 Feb
Pharmacological characterization of a novel antiglaucoma agent, Bimatoprost (AGN 192024).
2003 May
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.
2004 Aug
Mechanism of ocular hypotensive action of bimatoprost (Lumigan) in patients with ocular hypertension or glaucoma.
2004 Sep
Bimatoprost: mechanism of ocular surface hyperemia associated with topical therapy.
2005 Fall
Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy.
2006 Apr
Prospective comparative switch study from timolol 0.5% and latanoprost 0.005% to bimatoprost 0.03%.
2006 Jan-Feb
Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma.
2006 Jun
[Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?].
2006 Jun
Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure.
2007 Dec
Bimatoprost, prostamide activity, and conventional drainage.
2007 Sep
Bimatoprost, the prodrug of a prostaglandin analogue.
2008 Jun
Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study.
2008 May
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response.
2009 Aug
Bimatoprost - a review.
2009 Nov
Patents

Sample Use Guides

One drop in the affected eye(s) once daily in the evening
Route of Administration: Other
In Vitro Use Guide
Curator's Comment:: To examine the protective effects of bimatoprost, cultured retinal ganglion cells (RGC) with various concentrations of bimatoprost (in both free acid and amide form) were exposed to l-buthionin-(S,R)-sulfoximine (BSO) plus glutamate or serum depletion in vitro and intravitreal injection of N-methyl-D-aspartate (NMDA) was used to induce retinal damage in vivo. To elucidate the protective mechanism of bimatoprost, we used western blot analysis to investigate the phosphorylation of Akt and extracellular signal-regulated kinase (ERK). Bimatoprost significantly reduced BSO plus glutamate- and serum deprivation-induced death in concentration-dependent manners. Bimatoprost induced activation of Akt and ERK, and a phosphatidylinositol 3-kinase inhibitor, LY294002, attenuated the protective effect of bimatoprost.
Unknown
Name Type Language
BIMATOPROST
EMA EPAR   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INCI   INN   USAN  
Official Name English
BIMATOPROST [MART.]
Common Name English
PROSTAMIDE
Brand Name English
GANFORT COMPONENT BIMATOPROST
Brand Name English
(Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3S)-3-HYDROXY-5-PHENYL-1-PENTENYL)CYCLOPENTYL)-N-ETHYL-5-HEPTENAMIDE
Systematic Name English
AGN 192024
Code English
BIMATOPROST [INN]
Common Name English
AGN-192024
Code English
BIMATOPROST [USAN]
Common Name English
BIMATOPROST [ORANGE BOOK]
Common Name English
LATISSE
Brand Name English
5-HEPTENAMIDE, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-5-PHENYL-1-PENTENYL)CYCLOPENTYL)-N-ETHYL-, (1R-1(.ALPHA.(Z),2.BETA.(1E,3S*)3.ALPHA.,5.ALPHA.))-
Common Name English
BIMATOPROST [WHO-DD]
Common Name English
BIMATOPROST [INCI]
Common Name English
BIMATOPROST [MI]
Common Name English
BIMATOPROST [VANDF]
Common Name English
LUMIGAN
Brand Name English
BIMATOPROST [JAN]
Common Name English
BIMATOPROST COMPONENT OF GANFORT
Brand Name English
BIMATOPROST [EMA EPAR]
Common Name English
DURYSTA
Brand Name English
Classification Tree Code System Code
NDF-RT N0000007706
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
WHO-ATC S01EE03
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
NDF-RT N0000007706
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
NCI_THESAURUS C78568
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
NDF-RT N0000007706
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
NCI_THESAURUS C29705
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
WHO-VATC QS01EE03
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
EMA ASSESSMENT REPORTS LUMIGAN (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
EMA ASSESSMENT REPORTS GANFORT (AUTHORIZED: OCULAR HYPERTENSION0
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
EMA ASSESSMENT REPORTS BIMATOPROST (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
EMA ASSESSMENT REPORTS LUMIGAN (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
NDF-RT N0000175454
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
Code System Code Type Description
INN
8035
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
WIKIPEDIA
BIMATOPROST
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
LACTMED
Bimatoprost
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
EVMPD
SUB12470MIG
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
IUPHAR
1958
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
PUBCHEM
5311027
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
FDA UNII
QXS94885MZ
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200963
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
NCI_THESAURUS
C47414
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
CAS
155206-00-1
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
DRUG BANK
DB00905
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
DRUG CENTRAL
371
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
MESH
C420823
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY
RXCUI
283810
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M2495
Created by admin on Sat Jun 26 16:13:49 UTC 2021 , Edited by admin on Sat Jun 26 16:13:49 UTC 2021
PRIMARY Merck Index