BIMATOPROST

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022184s005lbl.pdf

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 Target	Pharmacology	Condition	Potency
Prostanoid FP receptor 21 Target ID: CHEMBL1987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14733708	Agonist 2678		681.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 51 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022184s005lbl.pdf	Palliative		Approved 8429	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 2010
Ocular hypertension 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022184s005lbl.pdf	Primary		Approved 8429	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 2010

C_max

Value	Dose	Co-administered	Analyte	Population
0.08 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021275s022lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021275s022lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
0.09 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021275s022lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
45 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021275s022lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
12% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021275s022lbl.pdf	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf Page: p. 52	unhealthy, adult n = 137 Health Status: unhealthy Age Group: adult Population Size: 137 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 186 Health Status: unhealthy Age Group: adult Population Size: 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf Page: p. 52	unhealthy, adult n = 137 Health Status: unhealthy Age Group: adult Population Size: 137 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf Page: p. 52	unhealthy, adult n = 137 Health Status: unhealthy Age Group: adult Population Size: 137 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf Page: p. 52	unhealthy, adult n = 137 Health Status: unhealthy Age Group: adult Population Size: 137 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf Page: p. 52	unhealthy, adult n = 137 Health Status: unhealthy Age Group: adult Population Size: 137 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 186 Health Status: unhealthy Age Group: adult Population Size: 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 186 Health Status: unhealthy Age Group: adult Population Size: 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 186 Health Status: unhealthy Age Group: adult Population Size: 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 186 Health Status: unhealthy Age Group: adult Population Size: 186 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28	unhealthy, adult n = 188 Health Status: unhealthy Age Group: adult Population Size: 188 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf Page: p. 28

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 402 MRP2 383 MRP3 157 MRP4 204	CYP3A4/5 85 P-gp 1537 MRP2 205 BCRP 561

Drug as perpetrator

Target	Modality	Activity
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 40.4 uM]

Drug as victim

Target	Modality	Activity	Metabolite
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no	BIMATOPROST ACID 1
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no	BIMATOPROST ACID 1
CYP3A4/5 85	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21275_Lumigan%200.03%20percent%20Opthalmis%20Solution_pharmr_P1.pdf Page: 26.0	yes
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	yes
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/, https://pubmed.ncbi.nlm.nih.gov/23956101/	yes	BIMATOPROST ACID 1
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51230	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51230
ChemicalBook	CB0171421	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0171421
MolPort	MolPort-006-167-657	https://www.molport.com/shop/molecule-link/MolPort-006-167-657
ZINC	ZINC000004474405	http://zinc15.docking.org/substances/ZINC000004474405
eMolecules	26751504	https://www.emolecules.com/cgi-bin/more?vid=26751504

PubMed

Title	Date	PubMed
Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension.	2002	12027782
One-year, randomized study comparing bimatoprost and timolol in glaucoma and ocular hypertension.	2002 Oct	12365906
Hydrolysis of bimatoprost (Lumigan) to its free acid by ocular tissue in vitro.	2003 Feb	12648303
Pharmacological characterization of a novel antiglaucoma agent, Bimatoprost (AGN 192024).	2003 May	12606640
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.	2004 Aug	15321024
Mechanism of ocular hypotensive action of bimatoprost (Lumigan) in patients with ocular hypertension or glaucoma.	2004 Sep	15350319
Bimatoprost: mechanism of ocular surface hyperemia associated with topical therapy.	2005 Fall	16252016
Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy.	2006 Apr	16567279
Prospective comparative switch study from timolol 0.5% and latanoprost 0.005% to bimatoprost 0.03%.	2006 Jan-Feb	16644608
Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma.	2006 Jun	16808680
[Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?].	2006 Jun	16804825
Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure.	2007 Dec	17459480
Bimatoprost, prostamide activity, and conventional drainage.	2007 Sep	17724194
Bimatoprost, the prodrug of a prostaglandin analogue.	2008 Jun	18523093
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response.	2009 Aug	19403113
Bimatoprost - a review.	2009 Nov	19874254

Patents

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

Name

Type

Language

BIMATOPROST

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 [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

Bimatoprost [WHO-DD]

Common Name

English

DURYSTA

Brand Name

English

Classification Tree Code System Code

NDF-RT

N0000007706