CAS 155206-00-1|Bimatoprost|bimatoprost|Lumigan|AGN 192024|bimatoprost|(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|(5Z)-7-[(1R,...

General Information

Structure

Molecular Formula

C₂₅H₃₇NO₄

Molecular Mass

415.56558

Exact Mass

415.27225867

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

14.34702

H Acceptors

H Donor

LogD (pH = 5.5)

2.6292617

LogD (pH = 7.4)

2.6292624

Log P

2.6292624

Molar Refractivity

122.8312

Polarizability

47.097137

Polar Surface Area

89.79

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.41

LOG S

-4.35

Solubility (Water)

1.87e-02 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

bimatoprost

Brand Name

Lumigan

Synonyms

BimatoprostAGN 192024bimatoprostAGN-192024Lumigan(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamideProstamide

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

Names and Identifiers

Registration numbers

PubChem CID

5311027

PubChem SID

16096424446505334

CAS Number

155206-00-1

Registration numbers

Properties

Safety Information

MSDS Link

Download link

Storage Condition

Amber Vial, -20°C Freezer, Under Inert Atmosphere

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00905

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]

TRC

B386800

Bimatoprost is an antiglaucoma agent. Bimatoprost is an synthetic prostamide; structurally related to prostaglandin F2α.

Molecule Details

References

PubChem Literature

From Data Sources

• Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. 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

• Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. Pubmed

• Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. 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

• Brandt, J.D., et al.: Ophthalmology, 108, 1023 (2001)

• Quinones, R., et al.: J. Ocul. Pharmacol. Ther., 20, 115 (2001)

• Woodward, D.F., et al.: J. Pharmacol. Exp. Ther., 305, 772 (2001)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• IUPAC Traditional name

• Brand Name

• Synonyms

• IUPAC name

Registration numbers

• PubChem CID

• PubChem SID

• CAS Number

Properties

• Physical Property

• Safety Information

• Product Information

Related Proteins

Molecular Spectra

Molecule Details

• DrugBank

• TRC

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Commercial Catalog

TRC

B386800

IUPAC Traditional name

bimatoprost

Synonyms

BimatoprostAGN 192024bimatoprostAGN-192024Lumigan(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamideProstamide

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

PubChem SID

16096424446505334

CAS Number

155206-00-1

Physical Property

Safety Information

MSDS Link

Download link

Storage Condition

Amber Vial, -20°C Freezer, Under Inert Atmosphere

Product Information

Certificate of Analysis

Download link

DrugBank

DB00905

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Toxicity

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]

• Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. [Pubmed]

• Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. [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]

TRC

B386800

Bimatoprost is an antiglaucoma agent. Bimatoprost is an synthetic prostamide; structurally related to prostaglandin F2α.

From Data Sources

• Brubaker RF: Mechanism of action of bimatoprost (Lumigan). Surv Ophthalmol. 2001 May;45 Suppl 4:S347-51. 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

• Steinhauser SL: Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy. Optometry. 2006 Apr;77(4):177-9. Pubmed

• Patil AJ, Vajaranant TS, Edward DP: Bimatoprost - a review. Expert Opin Pharmacother. 2009 Nov;10(16):2759-68. 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

• Brandt, J.D., et al.: Ophthalmology, 108, 1023 (2001)

• Quinones, R., et al.: J. Ocul. Pharmacol. Ther., 20, 115 (2001)

• Woodward, D.F., et al.: J. Pharmacol. Exp. Ther., 305, 772 (2001)

Molecule

ID:781