Identification

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Name
Bimatoprost
Accession Number
DB00905  (APRD00826, DB06863)
Type
Small Molecule
Groups
Approved, Investigational
Description

Bimatoprost, also known as Latisse or Lumigan, belongs to a group of drugs called prostamides, which are synthetic structural analogs of prostaglandin. Bimatoprost, marketed by Allergan, is administered in an ophthalmic solution and has the ability to reduce ocular hypotension, proving effective in conditions such as ocular hypertension and glaucoma.13,16,17 Bimatoprost is also used to treat eyelash hypotrichosis, or sparse eyelash growth.18 It was initially approved by the FDA in 2001 for ocular hypertension and later approved for hypothrichosis in 2008, as eyelash growth became a desirable adverse effect for patients using this drug.19

Structure
Thumb
Synonyms
  • (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide
  • Bimatoprost
  • Bimatoprostum
External IDs
AGN 192024 / AGN-192024
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LatisseSolution / drops0.3 mg/1mLOphthalmicAllergan2009-01-26Not applicableUs
LatisseSolution / drops0.3 mg/1mLOphthalmicPhysicians Total Care, Inc.2009-07-242013-06-30Us
LatisseSolution0.03 %TopicalAllergan2010-11-01Not applicableCanada
LumiganSolution / drops0.3 mg/1mLOphthalmicPhysicians Total Care, Inc.2001-03-22Not applicableUs
LumiganSolution0.3 mg/1mLOphthalmicAllergan, Inc.2006-11-132006-11-13Us
LumiganSolution / drops0.1 mg/1mLOphthalmicPhysicians Total Care, Inc.2011-09-14Not applicableUs
LumiganSolution / drops0.1 mg/1mLOphthalmicAllergan2010-09-10Not applicableUs
LumiganSolution0.03 %OphthalmicAllergan2002-05-24Not applicableCanada
Lumigan PFSolution0.03 %OphthalmicAllerganNot applicableNot applicableCanada
Lumigan RcSolution0.01 %OphthalmicAllergan2009-06-16Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bimatoprostSolution0.03 %TopicalApotex CorporationNot applicableNot applicableCanada
Apo-bimatoprostSolution0.03 %OphthalmicApotex CorporationNot applicableNot applicableCanada
BimatoprostSolution / drops0.3 mg/1mLOphthalmicSomerset Therapeutics, Llc2019-07-08Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicGland Pharma Limited2019-02-12Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicLupin Pharmaceuticals2015-05-13Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicSomerset Therapeutics, Llc2019-07-08Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicHi-Tech Pharmacal Co., Inc.2018-11-12Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicSandoz2016-12-06Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicSomerset Therapeutics, Llc2019-07-08Not applicableUs
BimatoprostSolution / drops0.3 mg/1mLOphthalmicApotex Corp.2018-10-08Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
QXS94885MZ
CAS number
155206-00-1
Weight
Average: 415.5656
Monoisotopic: 415.272258677
Chemical Formula
C25H37NO4
InChI Key
AQOKCDNYWBIDND-FTOWTWDKSA-N
InChI
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
IUPAC Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
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)CCC1=CC=CC=C1

Pharmacology

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.13

Bimatoprost is also indicated to treat eyelash hypotrichosis.18

Associated Conditions
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.13 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.13

Other effects of this drug may include gradual changes in eyelid pigmentation, changes in iris pigmentation, changes in eyelash pigmentation, growth and thickness.13 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.13

Mechanism of action

Bimatoprost imitates the effects of prostamides, specifically prostaglandin F2α.16 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.13 It achieves the above effects by decreasing tonographic resistance to aqueous humor outflow.6 Bimatoprost does not affect aqueous humor production.5

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Humans
AProstaglandin E2 receptor EP1 subtype
agonist
Humans
AProstaglandin E2 receptor EP3 subtype
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.13 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.13

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.17

Volume of distribution

The volume of distribution at steady state is 0.67 L/kg.13,17. It penetrates the human cornea and sclera.17

Protein binding

Bimatoprost is about 88%-90% bound to plasma proteins.13,16

Metabolism

Bimatoprost is hydrolyzed to its active form, bimatoprost acid, in the eye.20 Bimatoprost undergoes oxidation, N-deethylation, and glucuronidation after it is systemically absorbed, and this leads to the production of various metabolites.13 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.16 Glucuronidated metabolites comprise most of the excreted drug product in the blood, urine, and feces in rats.16

Route of elimination

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.13

Half life

The elimination half-life of bimatoprost is approximately 45 minutes.13,16

Clearance

The clearance was measured to be 1.5 L/hr/kg in healthy subjects receiving IV administration of bimatoprost dosed at 3.12 ug/kg.13,16

Toxicity

Oral LD50 in the rat is 980 mg/kg.15 No information is available at this time regarding bimatoprost overdose in humans. Provide supportive symptomatic treatment if an overdose occurs.13

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololBimatoprost may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Alclofenac.
AliskirenBimatoprost may increase the hypotensive activities of Aliskiren.
AlminoprofenThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Alminoprofen.
AlprenololAlprenolol may increase the hypotensive activities of Bimatoprost.
AmbrisentanBimatoprost may increase the hypotensive activities of Ambrisentan.
AminophenazoneThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Aminophenazone.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Jiang Xing Chen, "Process for the production of intermediates for making prostaglandin derivatives such as latanaprost, travaprost, and bimatoprost." U.S. Patent US20090287003, issued November 19, 2009.

US20090287003
General References
  1. Chen MJ, Cheng CY, Chen YC, Chou CK, Hsu WM: Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma. J Ocul Pharmacol Ther. 2006 Jun;22(3):188-93. [PubMed:16808680]
  2. Kruse P, Rieck P, Sherif Z, Liekfeld A: [Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?]. Klin Monbl Augenheilkd. 2006 Jun;223(6):534-7. [PubMed:16804825]
  3. Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. [PubMed:16567279]
  4. Woodward DF, Krauss AH, Chen J, Lai RK, Spada CS, Burk RM, Andrews SW, Shi L, Liang Y, Kedzie KM, Chen R, Gil DW, Kharlamb A, Archeampong A, Ling J, Madhu C, Ni J, Rix P, Usansky J, Usansky H, Weber A, Welty D, Yang W, Tang-Liu DD, Garst ME, Brar B, Wheeler LA, Kaplan LJ: The pharmacology of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S337-45. [PubMed:11434936]
  5. Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763]
  6. Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. [PubMed:11434937]
  7. Christiansen GA, Nau CB, McLaren JW, Johnson DH: Mechanism of ocular hypotensive action of bimatoprost (Lumigan) in patients with ocular hypertension or glaucoma. Ophthalmology. 2004 Sep;111(9):1658-62. [PubMed:15350319]
  8. Easthope SE, Perry CM: Topical bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension. Drugs Aging. 2002;19(3):231-48. [PubMed:12027782]
  9. Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. doi: 10.1517/14656560903292649. [PubMed:19874254]
  10. Woodward DF, Liang Y, Krauss AH: Prostamides (prostaglandin-ethanolamides) and their pharmacology. Br J Pharmacol. 2008 Feb;153(3):410-9. doi: 10.1038/sj.bjp.0707434. Epub 2007 Aug 27. [PubMed:17721551]
  11. Law SK: Bimatoprost in the treatment of eyelash hypotrichosis. Clin Ophthalmol. 2010 Apr 26;4:349-58. doi: 10.2147/opth.s6480. [PubMed:20463804]
  12. Jha AK, Sarkar R, Udayan UK, Roy PK, Jha AK, Chaudhary RKP: Bimatoprost in Dermatology. Indian Dermatol Online J. 2018 May-Jun;9(3):224-228. doi: 10.4103/idoj.IDOJ_62_16. [PubMed:29854658]
  13. Bimatoprost FDA label [Link]
  14. Bimatoprost MSDS [Link]
  15. MSDS Bimatoprost [Link]
  16. Allergen monograph, Bimatoprost [Link]
  17. Bitamaprost MedSafe NZ [Link]
  18. Latisse FDA label [Link]
  19. FDA approvals [Link]
  20. Bimataprost metabolism, MDPI [Link]
External Links
Human Metabolome Database
HMDB0015041
KEGG Drug
D02724
PubChem Compound
5311027
PubChem Substance
46505334
ChemSpider
4470565
BindingDB
220120
ChEBI
51230
ChEMBL
CHEMBL1200963
Therapeutic Targets Database
DAP001217
PharmGKB
PA164748867
Guide to Pharmacology
GtP Drug Page
HET
15M
Wikipedia
Bimatoprost
ATC Codes
S01EE03 — Bimatoprost
AHFS Codes
  • 52:40.28 — Prostaglandin Analogs
PDB Entries
2f38

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentDermatochalasis1
0RecruitingTreatmentGraves Ophthalmopathy1
1TerminatedTreatmentAndrogenetic Alopecia / Hair Thinning1
1, 2CompletedTreatmentGlaucoma / Ocular Hypertension1
1, 2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)2
2Active Not RecruitingPreventionHeadache Disorders / Migraine Disorders1
2CompletedTreatmentAndrogenetic Alopecia / Male Pattern Hair Loss1
2CompletedTreatmentEyelash Hypotrichosis1
2CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension5
2CompletedTreatmentGlaucoma / Ocular Hypertension3
2CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)3
2, 3CompletedTreatmentOcular Hypertension1
3CompletedTreatmentEyebrow Hypotrichosis1
3CompletedTreatmentEyelash Hypotrichosis2
3CompletedTreatmentEyelashes1
3CompletedTreatmentGlaucoma1
3CompletedTreatmentGlaucoma / Ocular Hypertension2
3CompletedTreatmentHypotrichosis1
3CompletedTreatmentHypotrichosis / Madarosis1
3CompletedTreatmentIdiopathic Eyelash Hypotrichosis1
3CompletedTreatmentThyroid Associated Ophthalmopathy1
3Not Yet RecruitingTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)1
3RecruitingPreventionGlaucoma1
3RecruitingTreatmentGlaucoma / Ocular Hypertension1
3RecruitingTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedNot AvailableGlaucoma1
4CompletedNot AvailableGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4CompletedTreatmentAlopecia Areata (AA) / Eyelash Hypotrichosis1
4CompletedTreatmentAnterior Uveitis (AU) / Cystoid Macular Edema1
4CompletedTreatmentApplication Site Pigmentation Changes / Glaucoma1
4CompletedTreatmentCataracts1
4CompletedTreatmentCrow's Feet Lines / Facial Rhytides / Glabellar Lines / Nasolabial Folds1
4CompletedTreatmentEndocrine ophthalmopathy1
4CompletedTreatmentEyelash Hypotrichosis1
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Intraocular Pressure / Ocular Hypertension1
4CompletedTreatmentGlaucoma / Ocular Hypertension10
4CompletedTreatmentGlaucoma / Ocular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedTreatmentHypotrichosis4
4CompletedTreatmentNormal Tension Glaucoma / Open-angle Glaucoma (OAG)1
4CompletedTreatmentOcular Hypertension1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG)2
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)6
4CompletedTreatmentOpen-angle Glaucoma (OAG)2
4RecruitingTreatmentGlaucoma1
4RecruitingTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
4RecruitingTreatmentGlaucoma / Ocular Hypertension1
4WithdrawnPreventionGlaucoma / Ocular Hypertension / Thyroid Eye Disease1
4WithdrawnTreatmentRepigmentation / Vitiligo1
Not AvailableActive Not RecruitingTreatmentIntraocular Pressure / Nail Growth Cessation1
Not AvailableCompletedNot AvailableEyelash Hypotrichosis2
Not AvailableCompletedNot AvailableGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension1
Not AvailableCompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)8
Not AvailableCompletedTreatmentAlopecia Areata (AA)1
Not AvailableCompletedTreatmentHypertrichosis1
Not AvailableCompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
Not AvailableTerminatedTreatmentGlaucoma1
Not AvailableUnknown StatusTreatmentGlaucoma, Angle-Closure1
Not AvailableUnknown StatusTreatmentOcular Hypertension / Primary Glaucoma1
Not AvailableWithdrawnSupportive CareCancer, Breast / Hair Thinning1

Pharmacoeconomics

Manufacturers
  • Allergan inc
Packagers
  • Allergan Inc.
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
SolutionOphthalmic0.03 %
SolutionTopical3 ug/1mL
SolutionTopical0.03 %
SolutionOphthalmic0.3 mg/1mL
Solution / dropsOphthalmic0.1 mg/1mL
Solution / dropsOphthalmic0.3 mg/1mL
SolutionOphthalmic0.01 %
Prices
Unit descriptionCostUnit
Lumigan .03% 7.5ml Bottle279.56USD bottle
Lumigan .03% 5ml Bottle171.4USD bottle
Lumigan .03% 2.5ml Bottle91.16USD bottle
Lumigan 0.03% eye drops44.82USD ml
Latisse 0.03% eyelash solution36.0USD ml
Lumigan 0.03 % Solution12.18USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6403649No2002-06-112012-09-21Us
CA2585691No2009-05-192026-03-14Canada
CA2144967No2003-11-112013-09-09Canada
US8299118No2012-10-302025-03-16Us
US8309605No2012-11-132025-03-16Us
US8338479No2012-12-252025-03-16Us
US8586630No2013-11-192025-03-16Us
US8524777No2013-09-032025-03-16Us
US8772338No2014-07-082025-03-16Us
US9155716No2015-10-132025-03-16Us
US9241918No2016-01-262025-03-16Us
US7851504No2010-12-142027-06-13Us
US8933120No2015-01-132025-03-16Us
US8933127No2015-01-132025-03-16Us
US8278353No2012-10-022025-03-16Us
US8906962No2014-12-092021-01-31Us
US8038988No2011-10-182023-08-25Us
US8101161No2012-01-242024-05-25Us
US8263054No2012-09-112023-01-15Us
US8632760No2014-01-212023-01-15Us
US8758733No2014-06-242023-01-15Us
US8926953No2015-01-062023-01-15Us
US8541466No2013-09-242021-01-31Us
US7388029No2008-06-172022-01-21Us
US7351404No2008-04-012024-05-25Us
US9216183No2015-12-222023-01-15Us
US9226931No2016-01-052023-01-15Us
US8986715No2015-03-242023-01-15Us
US9579270No2017-02-282021-01-31Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)63-67https://mri.cts-mrp.eu/Human/Downloads/PT_H_1188_001_PAR.pdf
boiling point (°C)629.8 https://mri.cts-mrp.eu/Human/Downloads/PT_H_1188_001_PAR.pdf
water solubilitysoluble in waterhttps://mri.cts-mrp.eu/Human/Downloads/PT_H_1188_001_PAR.pdf
logP3.2http://www.hmdb.ca/metabolites/HMDB0015041
pKa14.3, - 0.23http://www.hmdb.ca/metabolites/HMDB0015041
Predicted Properties
PropertyValueSource
Water Solubility0.0187 mg/mLALOGPS
logP3.41ALOGPS
logP2.63ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity122.83 m3·mol-1ChemAxon
Polarizability48.24 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9975
Blood Brain Barrier+0.825
Caco-2 permeable-0.5699
P-glycoprotein substrateSubstrate0.5541
P-glycoprotein inhibitor INon-inhibitor0.8671
P-glycoprotein inhibitor IINon-inhibitor0.8616
Renal organic cation transporterNon-inhibitor0.8078
CYP450 2C9 substrateNon-substrate0.7703
CYP450 2D6 substrateNon-substrate0.7406
CYP450 3A4 substrateSubstrate0.552
CYP450 1A2 substrateNon-inhibitor0.6764
CYP450 2C9 inhibitorNon-inhibitor0.7695
CYP450 2D6 inhibitorNon-inhibitor0.6384
CYP450 2C19 inhibitorNon-inhibitor0.7632
CYP450 3A4 inhibitorNon-inhibitor0.757
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7049
Ames testNon AMES toxic0.7646
CarcinogenicityNon-carcinogens0.9257
BiodegradationNot ready biodegradable0.6415
Rat acute toxicity2.1085 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9251
hERG inhibition (predictor II)Non-inhibitor0.7822
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
N-acyl amines / Cyclopentanols / Benzene and substituted derivatives / Secondary carboxylic acid amides / Cyclic alcohols and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Prostaglandin skeleton / Monocyclic benzene moiety / Cyclopentanol / Fatty amide / Benzenoid / N-acyl-amine / Cyclic alcohol / Carboxamide group / Secondary carboxylic acid amide / Secondary alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide (CHEBI:51230)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin f receptor activity
Specific Function
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis...
Gene Name
PTGFR
Uniprot ID
P43088
Uniprot Name
Prostaglandin F2-alpha receptor
Molecular Weight
40054.1 Da
References
  1. Sharif NA, Williams GW, Kelly CR: Bimatoprost and its free acid are prostaglandin FP receptor agonists. Eur J Pharmacol. 2001 Dec 7;432(2-3):211-3. [PubMed:11740958]
  2. Sharif NA, Kelly CR, Crider JY: Agonist activity of bimatoprost, travoprost, latanoprost, unoprostone isopropyl ester and other prostaglandin analogs at the cloned human ciliary body FP prostaglandin receptor. J Ocul Pharmacol Ther. 2002 Aug;18(4):313-24. [PubMed:12222762]
  3. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  4. Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763]
  5. Mintz EE: Group supervision: an experiential approach. Int J Group Psychother. 1978 Oct;28(4):467-9. [PubMed:689791]
  6. Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines]. Oftalmologia. 2009;53(2):3-7. [PubMed:19697832]
  7. Wan Z, Woodward DF, Cornell CL, Fliri HG, Martos JL, Pettit SN, Wang JW, Kharlamb AB, Wheeler LA, Garst ME, Landsverk KJ, Struble CS, Stamer WD: Bimatoprost, prostamide activity, and conventional drainage. Invest Ophthalmol Vis Sci. 2007 Sep;48(9):4107-15. [PubMed:17724194]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
Molecular Weight
41800.655 Da
References
  1. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  2. Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
Gene Name
PTGER3
Uniprot ID
P43115
Uniprot Name
Prostaglandin E2 receptor EP3 subtype
Molecular Weight
43309.335 Da
References
  1. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [PubMed:14733708]
  2. Gabelt BT, Hennes EA, Bendel MA, Constant CE, Okka M, Kaufman PL: Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys. J Ocul Pharmacol Ther. 2009 Feb;25(1):1-8. doi: 10.1089/jop.2008.0089. [PubMed:19232013]
  3. Ota T, Aihara M, Saeki T, Narumiya S, Araie M: The effects of prostaglandin analogues on prostanoid EP1, EP2, and EP3 receptor-deficient mice. Invest Ophthalmol Vis Sci. 2006 Aug;47(8):3395-9. [PubMed:16877408]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Allergen monograph, Bimatoprost [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Allergen monograph, Bimatoprost [Link]

Drug created on June 13, 2005 07:24 / Updated on July 21, 2019 06:28