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155206-00-1 分子结构
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(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

ChemBase编号:781
分子式:C25H37NO4
平均质量:415.56558
单一同位素质量:415.27225867
SMILES和InChIs

SMILES:
O[C@@H]1[C@@H]([C@H]([C@H](O)C1)/C=C/[C@@H](O)CCc1ccccc1)C/C=C\CCCC(=O)NCC
Canonical SMILES:
CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](CCc1ccccc1)O)O
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
InChIKey:
AQOKCDNYWBIDND-FTOWTWDKSA-N

引用这个纪录

CBID:781 http://www.chembase.cn/molecule-781.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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
IUPAC传统名
bimatoprost
商标名
Lumigan
别名
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide
AGN-192024
Lumigan
Prostamide
AGN 192024
bimatoprost
Bimatoprost
CAS号
155206-00-1
PubChem SID
160964244
46505334
PubChem CID
5311027

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
TRC
B386800 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.34702  质子受体
质子供体 LogD (pH = 5.5) 2.6292617 
LogD (pH = 7.4) 2.6292624  Log P 2.6292624 
摩尔折射率 122.8312 cm3 极化性 47.097137 Å3
极化表面积 89.79 Å2 可自由旋转的化学键 12 
里宾斯基五规则 true 
Log P 3.41  LOG S -4.35 
溶解度 1.87e-02 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
Slightly soluble expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
66-68°C expand 查看数据来源
疏水性(logP)
3.2 expand 查看数据来源
保存条件
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB00905 external link
Item Information
Drug Groups approved; investigational
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.
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.
Pharmacology 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.
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
Biotransformation Bimatoprost undergoes oxidation, N-deethylation and glucuronidation to form a variety of metabolites.
Absorption Systemically absorbed when administered to the eye.
Half Life Elimination half-life is approximately 45 minutes.
Protein Binding Approximately 88% of bimatoprost is bound in human plasma.
Elimination Up to 67% of the administered dose was excreted in the urine while 25% of the dose was recovered in the feces.
Distribution * 0.67 L/kg
Clearance * 1.5 L/hr/kg [Healthy subjects receiving IV administration of 3.12 ug/kg]
References
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]
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]
Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. [Pubmed]
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]
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]
Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. [Pubmed]
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]
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]
Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals -  B386800 external link
Bimatoprost is an antiglaucoma agent. Bimatoprost is an synthetic prostamide; structurally related to prostaglandin F2α.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. Pubmed
  • 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
  • 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
  • Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. Pubmed
  • 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
  • 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
  • Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. Pubmed
  • 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
  • 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
  • Brandt, J.D., et al.: Ophthalmology, 108, 1023 (2001)
  • Woodward, D.F., et al.: J. Pharmacol. Exp. Ther., 305, 772 (2001)
  • Quinones, R., et al.: J. Ocul. Pharmacol. Ther., 20, 115 (2001)
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