Please Wait
Applying Filters...
Menu
$ API Ref.Price (USD/KG) : 655,243Xls
2D Structure
Also known as: 155206-00-1, Lumigan, Latisse, Agn 192024, Prostamide, Agn-192024
Molecular Formula
C25H37NO4
Molecular Weight
415.6  g/mol
InChI Key
AQOKCDNYWBIDND-FTOWTWDKSA-N
FDA UNII
QXS94885MZ

A cloprostenol-derived amide that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.
Bimatoprost is a Prostaglandin Analog.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
2.1.2 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
2.1.3 InChI Key
AQOKCDNYWBIDND-FTOWTWDKSA-N
2.1.4 Canonical SMILES
CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
2.1.5 Isomeric SMILES
CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
2.2 Other Identifiers
2.2.1 UNII
QXS94885MZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 192024, Agn

2. Agn 192024

3. Latisse

4. Lumigan

2.3.2 Depositor-Supplied Synonyms

1. 155206-00-1

2. Lumigan

3. Latisse

4. Agn 192024

5. Prostamide

6. Agn-192024

7. (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3s)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-n-ethylhept-5-enamide

8. Qxs94885mz

9. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3s)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-n-ethyl-5-heptenamide

10. Chebi:51230

11. (e)-7-[3,5-dihydroxy-2-[(e)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-n-ethylhept-5-enamide

12. Bimatoprostum

13. Unii-qxs94885mz

14. (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

15. (5z)-7-{(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3s)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl}-n-ethylhept-5-enamide

16. Lumigan (tn)

17. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)-n-ethylhept-5-enamide

18. (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

19. Bimatoprost [usan:inn:ban:jan]

20. Bimatoprost In Bulk

21. Latisse (tn)

22. Durysta

23. Ls-181817

24. Bimatoprost [mi]

25. Bimatoprost [inn]

26. Bimatoprost [jan]

27. (5z)-bimatoprost

28. Bimatoprost [inci]

29. Bimatoprost [usan]

30. Bimatoprost [vandf]

31. Bimatoprost [mart.]

32. Schembl24425

33. Bimatoprost [who-dd]

34. 5-heptenamide, 7-(3,5-dihydroxy-2-(3-hydrdoxy-5-phenyl-1-pentenyl)cyclopentyl)-n-ethyl-, (1r-(1alpha(z),2beta(1e,3s*),3alpha,5alpha))-

35. Mls006010039

36. Us9271961, Bimatoprost

37. Bimatoprost (jan/usan/inn)

38. Bimatoprost [ema Epar]

39. Gtpl1958

40. Chembl1200963

41. Bimatoprost [orange Book]

42. Dtxsid30895042

43. Bdbm220120

44. Ex-a1769

45. Ganfort Component Bimatoprost

46. Hy-b0191

47. Zinc4474405

48. Mfcd03411999

49. Akos015995566

50. Am84507

51. Bimatoprost Component Of Ganfort

52. Db00905

53. Fd10460

54. Ncgc00181745-01

55. Ncgc00181745-03

56. 5-heptenamide, 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((1e,3s)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-n-ethyl-, (5z)-

57. 5-heptenamide, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-n-ethyl-, (1r-1(alpha(z),2beta(1e,3s*)3alpha,5alpha))-

58. As-35082

59. Smr000058996

60. B6165

61. D02724

62. 206b001

63. Sr-01000942224

64. Q2393348

65. Sr-01000942224-1

66. 17-phenyl Trinor Prostaglandin F2alpha Ethyl Amide

67. 17-phenyl-tri-norprostaglandin F2alpha-ethyl Amide, >=95%, Solid

68. 15m

69. 5-heptenamide, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-n-ethyl-, (1r-1(.alpha.(z),2.beta.(1e,3s*)3.alpha.,5.alpha.))-

70. 5-heptenamide, 7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3s)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-n-ethyl-, (5z)-

2.4 Create Date
2005-12-16
3 Chemical and Physical Properties
Molecular Weight 415.6 g/mol
Molecular Formula C25H37NO4
XLogP32.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count12
Exact Mass415.27225866 g/mol
Monoisotopic Mass415.27225866 g/mol
Topological Polar Surface Area89.8 Ų
Heavy Atom Count30
Formal Charge0
Complexity541
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameBimatoprost
PubMed HealthBimatoprost (Into the eye)
Drug ClassesAntiglaucoma, Ophthalmologic Agent
Drug LabelLATISSE (bimatoprost ophthalmic solution) 0.03% is a synthetic prostaglandin analog. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-5-heptenamide, and its molecular weight is 41...
Active IngredientBimatoprost
Dosage FormSolution
Routeophthalmic
Strength0.01%; 0.03%; 0.03
Market StatusTentative Approval
CompanyApotex; Sandoz

2 of 6  
Drug NameLatisse
PubMed HealthBimatoprost (Into the eye)
Drug ClassesAntiglaucoma, Ophthalmologic Agent
Drug LabelLATISSE (bimatoprost ophthalmic solution) 0.03% is a synthetic prostaglandin analog. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-5-heptenamide, and its molecular weight is 41...
Active IngredientBimatoprost
Dosage FormSolution/drops
RouteTopical
Strength0.03%
Market StatusPrescription
CompanyAllergan

3 of 6  
Drug NameLumigan
Drug LabelLUMIGAN 0.01% and 0.03% (bimatoprost ophthalmic solution) is a synthetic prostamide analog with ocular hypotensive activity. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-N-ethylhept...
Active IngredientBimatoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.01%
Market StatusPrescription
CompanyAllergan

4 of 6  
Drug NameBimatoprost
PubMed HealthBimatoprost (Into the eye)
Drug ClassesAntiglaucoma, Ophthalmologic Agent
Drug LabelLATISSE (bimatoprost ophthalmic solution) 0.03% is a synthetic prostaglandin analog. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-5-heptenamide, and its molecular weight is 41...
Active IngredientBimatoprost
Dosage FormSolution
Routeophthalmic
Strength0.01%; 0.03%; 0.03
Market StatusTentative Approval
CompanyApotex; Sandoz

5 of 6  
Drug NameLatisse
PubMed HealthBimatoprost (Into the eye)
Drug ClassesAntiglaucoma, Ophthalmologic Agent
Drug LabelLATISSE (bimatoprost ophthalmic solution) 0.03% is a synthetic prostaglandin analog. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-5-heptenamide, and its molecular weight is 41...
Active IngredientBimatoprost
Dosage FormSolution/drops
RouteTopical
Strength0.03%
Market StatusPrescription
CompanyAllergan

6 of 6  
Drug NameLumigan
Drug LabelLUMIGAN 0.01% and 0.03% (bimatoprost ophthalmic solution) is a synthetic prostamide analog with ocular hypotensive activity. Its chemical name is (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-N-ethylhept...
Active IngredientBimatoprost
Dosage FormSolution/drops
RouteOphthalmic
Strength0.01%
Market StatusPrescription
CompanyAllergan

4.2 Drug Indication

Bimatoprost is used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. These patients must be intolerant to other intraocular pressure lowering medications or inadequately responsive to other treatments. Bimatoprost is also indicated to treat eyelash hypotrichosis.


Reduction of elevated intraocular pressure in chronic open-angle glaucoma and ocular hypertension (as monotherapy or as adjunctive therapy to beta-blockers).


Treatment of glaucoma, Treatment of non-scarring hair loss


Treatment of androgenic alopecia


5 Pharmacology and Biochemistry
5.1 Pharmacology

High intraocular pressure is a major risk factor for glaucoma-related visual field loss. A linear relationship exists between intraocular pressure and the risk of damaging the optic nerve, which can lead to considerable visual impairment. Therefore, conditions such as ocular hypertension and glaucoma can cause dangerous elevations of intraocular pressure. Bimatoprost rapidly decreases intraocular pressure and reduces the risk for visual field loss from ocular hypertension due to various causes. Other effects of this drug may include gradual changes in eyelid pigmentation, changes in iris pigmentation, changes in eyelash pigmentation, growth and thickness. Patients should be informed of these possible effects, especially if this drug is only administered to one eye, which may noticeably change in appearance with bimatoprost treatment.


5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
BIMATOPROST
5.3.2 FDA UNII
QXS94885MZ
5.3.3 Pharmacological Classes
Prostaglandins [CS]; Prostaglandin Analog [EPC]
5.4 ATC Code

S01EE03


S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EE - Prostaglandin analogues

S01EE03 - Bimatoprost


5.5 Absorption, Distribution and Excretion

Absorption

This drug is absorbed systemically when administered to the eye. A study was performed on 15 healthy volunteers and bimatoprost ophthalmic solution 0.03% was administered once daily for 14 days. The mean Cmax was approximately 0.08 ng/mL and AUC0-24hr was approximately 0.09 on days 7 and 14 of the study. By 10 minutes, peak blood concentration was achieved. Bimatoprost was not detectable at 1.5 hours after administration in most subjects. The maximum blood concentration in a study of 6 healthy volunteers was determined to be 12.2 ng/mL. Steady state was reached in the first week of dosing. One drug label mentions that onset of decreased intraocular pressure occurs approximately 4 hours after the first administration and the peak effect occurs in the range of 8-12 hours. Bimatoprost effects may last up to 24 hours.


Route of Elimination

One pharmacokinetic study of bimatoprost in 6 healthy volunteers determined that 67% of the administered dose was found to be excreted in the urine while 25% of the dose was recovered in the feces.


Volume of Distribution

The volume of distribution at steady state is 0.67 L/kg.. It penetrates the human cornea and sclera.


Clearance

The clearance was measured to be 1.5 L/hr/kg in healthy subjects receiving IV administration of bimatoprost dosed at 3.12 ug/kg.


5.6 Metabolism/Metabolites

Bimatoprost is hydrolyzed to its active form, bimatoprost acid, in the eye. Bimatoprost undergoes oxidation, N-deethylation, and glucuronidation after it is systemically absorbed, and this leads to the production of various metabolites. In vitro studies show that CYP3A4 is an enzyme that participates in the metabolism of bimatoprost. Despite this, many enzymes and pathways metabolize bimatoprost, therefore, no significant drug-drug interactions are likely to occur. Glucuronidated metabolites comprise most of the excreted drug product in the blood, urine, and feces in rats.


5.7 Biological Half-Life

The elimination half-life of bimatoprost is approximately 45 minutes.


5.8 Mechanism of Action

Bimatoprost imitates the effects of prostamides, specifically prostaglandin F2. Bimatoprost mildly stimulates aqueous humor outflow, relieving elevated intraocular pressure and decreasing the risk of optic nerve damage. It is thought that bimatoprost reduces intraocular pressure (IOP) in humans by causing an increase in outflow of the aqueous humor via the trabecular meshwork and uveoscleral pathways. It achieves the above effects by decreasing tonographic resistance to aqueous humor outflow. Bimatoprost does not affect aqueous humor production.