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Bimatoprost (marketed in the US, Canada and Europe by Allergan, under the trade name Lumigan) is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes.^[1] In December 2008, the indication to lengthen eyelashes was approved by the U.S. Food and Drug Administration (FDA); the cosmetic formulation of bimatoprost is sold as Latisse /ləˈtiːs/.^[2]

Uses

Medical

Bimatoprost is used for the treatment of open-angle glaucoma and ocular hypertension in adult patients, either alone or in combination with a beta blocker^[3]^[4] (typically timolol).

Studies have shown bimatoprost to be more effective than timolol in reduction of intraocular pressure (IOP) and as least as effective as the prostaglandin analogs latanoprost and travoprost in reducing IOP.^[5]

Cosmetic

In patients using ophthalmic prostaglandins such as travoprost and latanoprost, it has been noted that there had been an increase in diameter, density and length of eyelashes. A study published in May 2010 found that bimatoprost in a gel suspension, when applied at the base of the upper eyelid eyelashes, significantly increased eyelash length.^{[citation needed]} Allergan initiated clinical trials investigating the usage of bimatoprost as a cosmetic drug.^[6] In 2008, the FDA Dermatologic and Ophthalmic Drugs Advisory Committee voted to approve bimatoprost for the cosmetic use of darkening and lengthening eyelashes.^[7] The medical term for this is treatment of hypotrichosis; however, the FDA approval is for purely cosmetic purposes.^[8]^{[verification needed]}

Side effects

Side effects are similar to other prostaglandin analogs applied to the eye. The most common one is conjunctival hyperemia, which occurs in more than 10% of patients. Other effects include blurred vision, eye and eyelid redness, eye burning or other discomfort, and permanent darkening of the iris to brown.^[3]^[4]^[9] Occasional adverse effects (in less than 1% of patients) are headache and nausea.^[3]

Some side effects are specific to the cosmetic formulation, which is applied to the skin at the base of the eyelash rather than instilled into the eye. These include infection if the one-time applicators are reused, and darkening of the eyelid or of the area beneath the eye.^[9]^[10]

Interactions

No interaction studies with this substance have been performed. Interactions with systemic (for example, oral) drugs are considered unlikely because bimatoprost does not reach relevant concentrations in the bloodstream. Bimatoprost does not negatively interact with timolol eye drops.^[3]

Pharmacology

Mechanism of action

Bimatoprost is a structural analog of prostaglandin F_2α (PGF_2α). Like other PGF_2α analogs such as travoprost, latanoprost and tafluprost, it increases the outflow of aqueous fluid from the eye and lowers intraocular pressure. However, in contrast to these it does not act on the prostaglandin F receptor, nor on any other known prostaglandin receptor. It is thought that bimatoprost mimics the human body's own prostamides (which are chemically similar), a class of substances related to prostaglandins, but with an unknown mechanism of action.^[3]^[4] No prostamide receptor has been identified as of 2015^[update]; the search is ongoing.^[11]

Pharmacokinetics

Bimatoprost is well absorbed through the cornea. It starts lowering intraocular pressure after four hours, lasting for at least 24 hours. A low percentage enters the bloodstream. In the blood plasma, peak concentrations are reached after 10 minutes, then drop below the detection limit of 25 pg/ml after 1.5 hours. The substance does not accumulate in the body.^[3]^[4]

Plasma protein binding is 88%. Bimatoprost is metabolized by oxidation, N-deethylation and glucuronidation, forming a variety of metabolites. Biological half-life was measured to be 45 minutes after intravenous infusion. 67% are eliminated via the kidney, and 25% via the feces.^[3]^[4]

References

^ "Bimatoprost Ophthalmic". MedlinePlus. January 1, 2003. Archived from the original on 2007-10-05. Retrieved 2007-11-19.
^ "Allergan gets FDA approval for eyelash treatment". BusinessWeek. Associated Press. December 26, 2008. Retrieved December 26, 2008.
^ ^a ^b ^c ^d ^e ^f ^g Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
^ ^a ^b ^c ^d ^e Drugs.com: Bimatoprost Monograph.
^ Curran MP (2009). "Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension". Drugs Aging. 26 (12): 1049–71. doi:10.2165/11203210-000000000-00000. PMID 19929032.
^ Rundle, Rhonda L. (2007-11-19). "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. Retrieved 2007-11-19.
^ Grady, Scott. "Latisse (Bimatoprost) is Approved by the FDA in 2008". ChicLatisse.com. Retrieved 22 August 2014.
^ The Pink Sheet: [1] Lauren Smith, December 15, 2008; Volume 70, Number 050.
^ ^a ^b Latisse prescribing information
^ "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010
^ Shelnut, E. L.; Nikas, S. P.; Finnegan, D. F.; Chiang, N; Serhan, C. N.; Makriyannis, A (2015). "Design and synthesis of novel prostaglandin E₂ ethanolamide and glycerol ester probes for the putative prostamide receptor(s)". Tetrahedron Letters. 56 (11): 1411–1415. doi:10.1016/j.tetlet.2015.01.164. PMC 4422110. PMID 25960577.

Citations

Chen M, Cheng C, Chen Y, Chou C, Hsu W (2006). "Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma.". J Ocul Pharmacol Ther. 22 (3): 188–93. doi:10.1089/jop.2006.22.188. PMID 16808680.
Kruse P, Rieck P, Sherif Z, Liekfeld A (2006). "Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?". Klinische Monatsblätter für Augenheilkunde. 223 (6): 534–7. doi:10.1055/s-2005-858992. PMID 16804825.
Steinhäuser S (2006). "Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy.". Optometry. 77 (4): 177–9. doi:10.1016/j.optm.2006.02.001. PMID 16567279.
Park J, Cho HK, Moon JI (2011). "Changes to upper eyelid orbital fat from use of topical bimatoprost, travoprost, and latanoprost.". Japanese Ophthalmological Society. 55 (1): 22–27. doi:10.1007/s10384-010-0904-z. PMID 21331688.
Jayaprakasam A, Ghazi-Nouri S (2010). "Periorbital fat atrophy - an unfamiliar side effect of prostaglandin analogues.". Orbit. 29 (6): 357–359. doi:10.3109/01676830.2010.527028. PMID 21158579.
Filippopoulos T, Paula JS, Torun N, Hatton MP, Pasquale LR, Grosskreutz CL (2008). "Periorbital changes associated with topical bimatoprost.". Ophthalmology Plastic and Reconstructive Surgery. 24 (4): 302–307. doi:10.1097/IOP.0b013e31817d81df. PMID 18645437.

UpToDate Contents

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1. 先天性角化異常症とその他の短縮テロメア症候群 dyskeratosis congenita and other short telomere syndromes
2. 化学療法による脱毛 chemotherapy induced alopecia
3. 開放隅角緑内障：治療 open angle glaucoma treatment
4. 円形脱毛症のマネージメント management of alopecia areata
5. 尋常性白斑：マネージメントと予後 vitiligo management and prognosis

English Journal

Bimatoprost 0.01% vs bimatoprost 0.03%: a 12-month prospective trial of clinical and in vivo confocal microscopy in glaucoma patients.

Figus M1, Nardi M1, Piaggi P2, Sartini M1, Guidi G1, Martini L1, Lazzeri S1.Author information 1Ophthalmology Unit, Department of Surgical, Medical and Molecular Pathology, and Critical Area, University of Pisa, Pisa, Italy.2Department of Endocrinology and Metabolism, University of Pisa, Pisa, Italy.AbstractPurposeTo evaluate the safety of two commercially available formulations of bimatoprost eye drops: 0.03 and 0.01% ophthalmic solutions.MethodsThis was a randomized, prospective, parallel-group, open-label, cohort study. A total of 60 glaucoma patients (60 eyes) under bimatoprost 0.03% monotherapy since at least 1 year were enrolled. Selected patients were randomized to receive a single drop of bimatoprost 0.01% (n=30) or bimatoprost 0.03% (n=30) ophthalmic solutions for 12 months. Statistical analysis was performed using paired t-test and repeated measures ANOVA test.ResultsGlobal clinical score (the sum of pruritus, stinging/burning, blurred vision, sticky eye sensation, eye dryness sensation, and foreign body sensation) significantly decreased in the bimatoprost 0.01% group from baseline 4.7±3.8 to 2.9±2.3 (P<0.001) and 2.5±2.0 (P<0.001) at 6-month and 12-month follow-ups, respectively. Comparison between groups showed differences at both follow-up visits (P=0.003 and P<0.001, respectively). In vivo confocal microscopy revealed a significant increase in goblet cell density in the bimatoprost 0.01% group compared with the bimatoprost 0.03% group (P<0.001 at both follow-up visits). All functional parameters and conjunctival hyperemia improved in the bimatoprost 0.01% group at each follow-up visit (P<0.05) and in comparison with bimatoprost 0.03% (P<0.05).ConclusionThe results of this trial suggest that bimatoprost 0.01% eye drops seem to decrease the ocular discomfort with respect to bimatoprost 0.03% eye drops.Eye advance online publication, 17 January 2014; doi:10.1038/eye.2013.304.
Eye (London, England).Eye (Lond).2014 Jan 17. doi: 10.1038/eye.2013.304. [Epub ahead of print]
PurposeTo evaluate the safety of two commercially available formulations of bimatoprost eye drops: 0.03 and 0.01% ophthalmic solutions.MethodsThis was a randomized, prospective, parallel-group, open-label, cohort study. A total of 60 glaucoma patients (60 eyes) under bimatoprost 0.03% monotherapy si
PMID 24434659

Relative Efficacy and Safety of Preservative-free Latanoprost (T2345) for the Treatment of Open-Angle Glaucoma and Ocular Hypertension: An Adjusted Indirect Comparison Meta-Analysis of Randomized Clinical Trials.

Cucherat M, Stalmans I, Rouland JF.Author information *UMR CNRS 5558, Faculté de Médecine Laennec, Lyon ‡Ophthalmology Department, University of Lille, Lille, France †Ophthalmology Department, University Hospitals Leuven, Leuven, Belgium.AbstractAIM: : To assess the relative efficacy and tolerability of preservative-free latanoprost (T2345) compared with other prostaglandin analogues (PGA) for the treatment of open-angle glaucoma and ocular hypertension by adjusted indirect comparison meta-analysis.
Journal of glaucoma.J Glaucoma.2014 Jan;23(1):e69-75. doi: 10.1097/IJG.0b013e3182a075e6.
AIM: : To assess the relative efficacy and tolerability of preservative-free latanoprost (T2345) compared with other prostaglandin analogues (PGA) for the treatment of open-angle glaucoma and ocular hypertension by adjusted indirect comparison meta-analysis.METHODS: Randomized, controlled trials eva
PMID 23881267

Safety and efficacy of bimatoprost solution 0.03% topical application in patients with chemotherapy-induced eyelash loss.

Ahluwalia GS.Author information Clinical Dermatology R&D, Clinical Development, Allergan, Irvine, California, USA.AbstractFew dermatologic conditions carry as much anxiety and emotional distress as hair loss resulting from a disease condition such as alopecia areata or as a result of cytotoxic drug treatment, e.g., after chemotherapy. Bimatoprost 0.03% solution is a Food and Drug Administration-approved prescription product indicated for the treatment of eyelash hypotrichosis. The product was investigated in a double-masked, randomized, and placebo-controlled study in patients who had significant eyelash loss or hypotrichosis as a result of chemotherapy. Once-daily treatment with bimatoprost ophthalmic solution 0.03% to the upper eyelid margin restored eyelash growth and prominence more quickly than the slower, natural course of recovery observed in the vehicle control subjects. The eyelash prominence measured using a validated Global Eyelash Assessment (GEA) scale demonstrated a statistically significant increase over placebo following 6 months of treatment. Efficacy was also demonstrated using a validated objective digital image analysis methodology to show significant increase in eyelash length, thickness/fullness, and darkness in these patients. Bimatoprost was found to be well tolerated over the 1-year treatment period.
The journal of investigative dermatology. Symposium proceedings / the Society for Investigative Dermatology, Inc. [and] European Society for Dermatological Research.J Investig Dermatol Symp Proc.2013 Dec;16(1):S73-6. doi: 10.1038/jidsymp.2013.30.
Few dermatologic conditions carry as much anxiety and emotional distress as hair loss resulting from a disease condition such as alopecia areata or as a result of cytotoxic drug treatment, e.g., after chemotherapy. Bimatoprost 0.03% solution is a Food and Drug Administration-approved prescription pr
PMID 24326568

Japanese Journal

正常眼圧緑内障に対するトラボプロスト,タフルプロスト,ビマトプロストの眼圧下降効果の検討 (第22回日本緑内障学会)

田邉祐資,菅野誠,山下英俊
あたらしい眼科 29(8), 1131-1135, 2012-08
NAID 40019415652

ラタノプロスト効果不十分例の点眼をビマトプロストに切替えたときの眼圧下降効果と安全性の検討

広田篤,井上康,永山幹夫,相良健,岡田康志,古本淳士,木内良明
あたらしい眼科 = Journal of the eye 29(2), 259-265, 2012-02-29
NAID 10030234844

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「ビマトプロスト」

Bimatoprost
Systematic (IUPAC) name
	7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
Clinical data
Trade names	Lumigan
AHFS/Drugs.com	Monograph
MedlinePlus	a602030
License data	US DailyMed: 46098;
Pregnancy; category	US: C (Risk not ruled out); ;
Routes of; administration	Topical (eye drops)
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	Low
Protein binding	88%
Onset of action	4 hrs
Biological half-life	45 min after IV application
Duration of action	≥ 24 hrs
Excretion	67% renal, 25% fecal
Identifiers
CAS Number	155206-00-1
ATC code	S01EE03 (WHO)
PubChem	CID 5311027
IUPHAR/BPS	1958
DrugBank	DB00905
ChemSpider	4470565
UNII	QXS94885MZ
KEGG	D02724
ChEBI	CHEBI:51230
ChEMBL	CHEMBL1200963
Chemical data
Formula	C25H37NO4
Molar mass	415.566 g/mol
	SMILES O=C(NCC)CCC/C=C\C[C@H]2[C@@H](O)C[C@@H](O)[C@@H]2/C=C/[C@@H](O)CCc1ccccc1 ;
	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 ; Key:AQOKCDNYWBIDND-FTOWTWDKSA-N ;
(what is this?) (verify)

　　[★]

英: bimatoprost
商: ルミガン
関: 眼科用剤

[MedlinePlus-1] "Bimatoprost Ophthalmic". MedlinePlus. January 1, 2003. Archived from the original on 2007-10-05. Retrieved 2007-11-19.

[2] "Allergan gets FDA approval for eyelash treatment". BusinessWeek. Associated Press. December 26, 2008. Retrieved December 26, 2008.

[AC-3] ^ ^a ^b ^c ^d ^e ^f ^g Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.

[Drugs.com-4] Drugs.com: Bimatoprost Monograph.

[pmid19929032-5] Curran MP (2009). "Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension". Drugs Aging. 26 (12): 1049–71. doi:10.2165/11203210-000000000-00000. PMID 19929032.

[WSJ-19-11-2007-6] Rundle, Rhonda L. (2007-11-19). "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. Retrieved 2007-11-19.

[7] Grady, Scott. "Latisse (Bimatoprost) is Approved by the FDA in 2008". ChicLatisse.com. Retrieved 22 August 2014.

[ThePinkSheet15Dec2008-8] The Pink Sheet: [1] Lauren Smith, December 15, 2008; Volume 70, Number 050.

[Label-9] Latisse prescribing information

[10] "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010

[11] Shelnut, E. L.; Nikas, S. P.; Finnegan, D. F.; Chiang, N; Serhan, C. N.; Makriyannis, A (2015). "Design and synthesis of novel prostaglandin E₂ ethanolamide and glycerol ester probes for the putative prostamide receptor(s)". Tetrahedron Letters. 56 (11): 1411–1415. doi:10.1016/j.tetlet.2015.01.164. PMC 4422110. PMID 25960577.

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