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Identification
Name Bimatoprost
Accession Number DB00905 (APRD00826, DB06863)
Type small molecule
Groups approved
Description

Bimatoprost 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
AGN 192024
Salts Not Available
Brand names
Name Company
Lumigan
Brand mixtures Not Available
Categories
  • Antihypertensive Agents
  • Antiglaucomic Agents
CAS number 155206-00-1
Weight Average: 415.5656
Monoisotopic: 415.272258677
Chemical Formula C25H37NO4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzene and Derivatives
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Amino Ketones
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Alcohols and Polyols
Pharmacology
Indication For the reduction of elevated intraocular pressure in patients with open angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.
Pharmacodynamics Bimatoprost is a prostamide, a synthetic structural analog of prostaglandin with ocular hypotensive activity, that is chemically related to prostamide F. It selectively mimics the effects of naturally occurring substances, prostamides. Bimatoprost lowers intraocular pressure (IOP) in humans. 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.
Mechanism of action Bimatoprost is believed to lower intraocular pressure (IOP) in humans by increasing outflow of aqueous humor through both the trabecular meshwork and uveoscleral routes. Bimatoprost reduces the pressure in the eye by mimicking the action of a naturally-occuring prostaglandin. Prostaglandins are a group of chemicals found in many places in the body. In the eye, they increase the drainage of the aqueous humour out of the eyeball. Bimatoprost is a synthetic compound related to one of the natural prostaglandins, and works by increasing the drainage of aqueous humour out of the eyeball. Bimatoprost may also lower the rate of aqueous formation in the eye. Both these effects decrease the pressure within the eye.
Absorption Systemically absorbed when administered to the eye.
Volume of distribution
  • 0.67 L/kg
Protein binding Approximately 88% of bimatoprost is bound in human plasma.
Metabolism Bimatoprost undergoes oxidation, N-deethylation and glucuronidation to form a variety of metabolites.
Route of elimination Up to 67% of the administered dose was excreted in the urine while 25% of the dose was recovered in the feces.
Half life Elimination half-life is approximately 45 minutes.
Clearance
  • 1.5 L/hr/kg [Healthy subjects receiving IV administration of 3.12 ug/kg]
Toxicity In oral (by gavage) mouse and rat studies, doses up to 100 mg/kg/day did not produce any toxicity. This dose expressed as mg/m2 is at least 70 times higher than the accidental dose of one bottle of bimatoprost for a 10 kg child.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Allergan inc
Packagers
Dosage forms
Form Route Strength
Solution Ophthalmic
Prices
Unit description Cost Unit
Lumigan .03% 7.5ml Bottle 279.56 USD bottle
Lumigan .03% 5ml Bottle 171.4 USD bottle
Lumigan .03% 2.5ml Bottle 91.16 USD bottle
Lumigan 0.03% eye drops 44.82 USD ml
Latisse 0.03% eyelash solution 36.0 USD ml
Lumigan 0.03 % Solution 12.18 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 7351404 2004-05-25 2024-05-25
United States 6403649 1992-09-21 2012-09-21
Canada 2585691 2009-05-19 2026-03-14
Canada 2144967 2003-11-11 2013-09-09
Properties
State solid
Experimental Properties
Property Value Source
water solubility Slightly soluble Not Available
logP 3.2 Not Available
Predicted Properties
Property Value Source
water solubility 1.87e-02 g/l ALOGPS
logP 3.41 ALOGPS
logP 2.63 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 14.35 ChemAxon
pKa (strongest basic) -0.23 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 89.79 ChemAxon
rotatable bond count 12 ChemAxon
refractivity 122.83 ChemAxon
polarizability 48.99 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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 Monatsbl Augenheilkd. 2006 Jun;223(6):534-7. Pubmed
  3. Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. Pubmed
  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
  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. Pubmed
  6. Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. Pubmed
  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
  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
  9. Patil AJ, Vajaranant TS, Edward DP: Bimatoprost – a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. Pubmed
External Links
Resource Link
PubChem Compound 5311027 Link_out
PubChem Substance 46505334 Link_out
ChemSpider 4470565 Link_out
ChEBI 51230 Link_out
ChEMBL 51230 Link_out
Therapeutic Targets Database DAP001217 Link_out
PharmGKB PA164748867 Link_out
IUPHAR 1958 Link_out
Guide to Pharmacology 1958 Link_out
HET 15M Link_out
Drug Product Database 2245860 Link_out
RxList http://www.rxlist.com/cgi/generic2/bimatoprost.htm Link_out
Drugs.com http://www.drugs.com/cdi/bimatoprost-drops.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/lum1578.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Bimatoprost Link_out
ATC Codes
  • S01EE03
AHFS Codes
  • 52:92.00
PDB Entries Not Available
FDA label show (24.4 KB)
MSDS show (19.2 KB)
Interactions
Drug Interactions
Drug Interaction
Latanoprost The concomitant use of bimatoprost and latanoprost may result in increased intraocular pressure. Consider avoiding this combination of therapy. Monitor for paradoxical increases in intraocular pressure during concomitant use.
Food Interactions Not Available
Targets

1. Prostaglandin F2-alpha receptor

Pharmacological action: yes
Actions: agonist

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 in the corpus luteum

Organism class: human
UniProt ID: P43088 Link_out
Gene: PTGFR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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. Pubmed
  5. Mintz EE: Group supervision: an experiential approach. Int J Group Psychother. 1978 Oct;28(4):467-9. Pubmed
  6. Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines] Oftalmologia. 2009;53(2):3-7. Pubmed
  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
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin E2 receptor, EP1 subtype

Pharmacological action: yes
Actions: agonist

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 important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues

Organism class: human
UniProt ID: P34995 Link_out
Gene: PTGER1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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

3. Prostaglandin E2 receptor, EP3 subtype

Pharmacological action: yes
Actions: agonist

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 of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I proteins, and to an elevation of intracellular calcium. The various isoforms have identical ligand binding properties but can interact with different second messenger systems (By similarity)

Organism class: human
UniProt ID: P43115 Link_out
Gene: PTGER3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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. Pubmed
  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

4. Aldo-keto reductase family 1 member C3

Pharmacological action: unknown

Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9alpha,11beta- PGF2 to PGD2. Functions as a bi-directional 3alpha-, 17beta- and 20alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone

Organism class: human
UniProt ID: P42330 Link_out
Gene: AKR1C3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19