Bimatoprost (CED0005898)

Record Information
Version1.0
Creation Date2016-05-25 18:23:34 UTC
Update Date2026-08-22 05:30:33 UTC
Accession NumberCHEM022200
Identification
Common NameBimatoprost
ClassSmall Molecule
Description
Bimatoprost is an organic compound with the chemical formula C25H37NO4 and an average molecular weight of 415.57 g/mol. Bimatoprost belongs to the eicosanoids, a subclass of fatty acyls within the organic compounds. This substance is identified as an agonist of the Prostaglandin F2-alpha receptor (PTGFR), as well as the Prostaglandin E2 receptor EP1 subtype (PTGER1) and the Prostaglandin E2 receptor EP3 subtype (PTGER3). The compound is found in or released from four recorded sources. These include healthcare, pharmaceuticals and veterinary products, specifically miotics and antiglaucoma preparations, as well as antennas within electrical and electronic equipment. Additionally, it is associated with household cleaning and consumer products, including other smoking requisites and non electric simulated smoking devices. Recorded routes of exposure for Bimatoprost include topical, parenteral, and ophthalmic administration.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamideChEBI
BimatoprostumChEBI
LumiganKegg
LatisseKegg
AGN 192024HMDB
Chemical FormulaC25H37NO4
Average Molecular Mass415.566 g/mol
Monoisotopic Mass415.272 g/mol
CAS Registry Number155206-00-1
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
Traditional Namebimatoprost
SMILESCCNC(=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
InChI IdentifierInChI=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
InChI KeyAQOKCDNYWBIDND-FTOWTWDKSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Fatty amide
  • Benzenoid
  • N-acyl-amine
  • Cyclic alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.41ALOGPS
logP2.63ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-0.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity122.83 m³·mol⁻¹ChemAxon
Polarizability48.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-2419000000-01cbf5b797f0f438d1a6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-6231489000-2ec035b55530648dfa88Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000y-7009100000-04092b804050ddfef5c0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9002000000-cd73c6df4099f0d843a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9101000000-16cd33625e643fb8da2bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-1009800000-d208fb15379ead12ec34Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0295-3009200000-411ffd7d83662240aea7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9121000000-1eb5c2b9bed6afaed1efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ls-0009200000-73e1b5344b1922942139Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-067j-1139100000-af0949d973b14e6f3c11Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9711100000-ab9a2b1f75dd718a7e7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0031900000-a254c0c0de4b4706471cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-0029300000-f7b4a623bab1403ce58eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-009x-9367000000-ad7524b223adaec377ffNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
185.0Log mg/kg[100:330]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
2 pathways
Bimatoprost Action Pathway
Bimatoprost Action Pathway
Bimatoprost Drug Metabolism Action Pathway
Bimatoprost Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureProstaglandin F2-alpha receptorP37289Bos taurusPredicted (SEA)0.0778492
Solute carrier organic anion transporter family member 2A1 structureClick to view 3D structureSolute carrier organic anion transporter family member 2A1Q92959HumansPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier organic anion transporter family member 2A1Q9EPT5Mus musculusPredicted (SEA)0.155698
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)3.34752
Click to view 3D structureSolute carrier organic anion transporter family member 2B1Q9JHI3Rattus norvegicusPredicted (SEA)0.311397
Click to view 3D structureProstaglandin F2-alpha receptorP43117Mus musculusPredicted (SEA)0.778492
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)4.35956
Prostaglandin E2 receptor EP4 subtype structureClick to view 3D structureProstaglandin E2 receptor EP4 subtypeP35408HumansPredicted (SEA)4.7488
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansPredicted (SEA)4.98235
Prostacyclin receptor structureClick to view 3D structureProstacyclin receptorP43119HumansPredicted (SEA)2.72472
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)7.55137
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)6.46149
Click to view 3D structureProstaglandin D2 receptorQ13258HumansPredicted (SEA)7.23998
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP35375Mus musculusPredicted (SEA)4.98235
Click to view 3D structureProstaglandin E2 receptor EP3 subtypeP30557Mus musculusPredicted (SEA)7.16213
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeP32240Mus musculusPredicted (SEA)5.29375
Click to view 3D structureProstaglandin E2 receptor EP2 subtypeQ62053Mus musculusPredicted (SEA)4.98235
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)44.8412
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)50.5241
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)32.3074
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)64.7706
Click to view 3D structureProstaglandin E2 receptor EP4 subtypeQ28691Oryctolagus cuniculusPredicted (SEA)0.0778492
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)52.7818
Click to view 3D structureTransient receptor potential cation channel subfamily V member 1O35433Rattus norvegicusPredicted (SEA)11.5995
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)6.69503
Concentrations
Not Available
External Links
DrugBank IDDB00905
HMDB IDHMDB0015041
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID15M
Wikipedia LinkBimatoprost
Chemspider ID4470565
ChEBI ID51230
PubChem Compound ID5311027
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51.
3. 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.
4. 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.
5. Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9.
6. 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.
7. 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.
8. 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.
9. Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. doi: 10.1517/14656560903292649.
10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
11. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
12. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
13. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
14. The lipid handbook with CD-ROM