Bimatoprost

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H37NO4
Molecular Weight	415.5656
Optical Activity	( + )
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

Molecular Formula	C25H37NO4
Molecular Weight	415.5656
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	2
Optical Activity	UNSPECIFIED

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 2752		681.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 53 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022184s005lbl.pdf	Palliative		Approved 8583	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 52 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022184s005lbl.pdf	Primary		Approved 8583	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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf	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
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf	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
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf	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

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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022369s000_MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf
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	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022184Orig1s000MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550 MRP2 499 MRP3 246 MRP4 290	CYP3A4/5 91 P-gp 2052 MRP2 252 BCRP 697

Drug as perpetrator

Target	Modality	Activity
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 40.4 uM]

Drug as victim

Target	Modality	Activity	Metabolite
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no	BIMATOPROST ACID 1
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	no	BIMATOPROST ACID 1
CYP3A4/5 91	substrate 4014 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 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028257/, https://pubmed.ncbi.nlm.nih.gov/23956101/	yes	BIMATOPROST ACID 1
P-gp 2052	substrate 4014 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
eMolecules	26751504	https://www.emolecules.com/cgi-bin/more?vid=26751504
MolPort	MolPort-006-167-657	https://www.molport.com/shop/molecule-link/MolPort-006-167-657
ZINC	ZINC000004474405	http://zinc15.docking.org/substances/ZINC000004474405

PubMed

Title	Date	PubMed
Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension.	2002	12027782
Bimatoprost, prostamide activity, and conventional drainage.	2007 Sep	17724194
Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study.	2008 May	18452763
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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:28 GMT 2025`
Record UNII	QXS94885MZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Bimatoprost

Official Name

English

DURYSTA

Preferred Name

English

Bimatoprost [MART.]

Common Name

English

5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)-

Systematic 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

AGN192024

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?(Z),2?(1E,3S*),3?,5?]]-

Systematic Name

English

Bimatoprost [MI]

Common Name

English

Bimatoprost [VANDF]

Common Name

English

Lumigan

Brand Name

English

Bimatoprost [JAN]

Common Name

English

Bimatoprost [EMA EPAR]

Common Name

English

Bimatoprost [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007706