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41 API Suppliers, 13 USDMF, 6 JDMF, 3 EU WC, 4 KDMF, 24 NDC API, 31 Listed Suppliers, $ API Reference Price

41 API Suppliers
13 USDMF
6 JDMF
3 EU WC
4 KDMF
24 NDC API
31 Listed Suppliers
$ API Reference Price

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28 Drugs in Development

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7 Intermediates Suppliers

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121 FDF Dossiers, 22 FDA Orange Book, 59 Europe, 7 Canada, 10 Australia, 2 South Africa, 21 Listed Dossiers

121 FDF Dossiers
22 FDA Orange Book
59 Europe
7 Canada
10 Australia
2 South Africa
21 Listed Dossiers

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41 NEWS #PharmaBuzz

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2 US Medicaid Prescriptions, 45 Finished Drug Prices, 10 Annual Reports

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45 Finished Drug Prices
10 Annual Reports

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15 APIs, 3 FDF Dossiers

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24 US Patents, 7 Health Canada Patents

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24 US Patents
7 Health Canada Patents

REF. STANDARDS & IMPURITIES

1 Others

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1 Others

Cayman Bimatoprost

Synopsis

ACTIVE PHARMA INGREDIENTS

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FDF

FINISHED DOSAGE FORMULATIONS

121

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

702,036,859

Annual Reports (USD Million)

4,745

Finished Drug Prices

6EXCIPIENTS BY APPLICATIONS

Chemistry

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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

Bimatoprost

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 Formula	C₂₅H₃₇NO₄
Molecular Weight	415.6 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	12
Exact Mass	415.27225866 g/mol
Monoisotopic Mass	415.27225866 g/mol
Topological Polar Surface Area	89.8 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	541
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Bimatoprost
PubMed Health	Bimatoprost (Into the eye)
Drug Classes	Antiglaucoma, Ophthalmologic Agent
Drug Label	LATISSE (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 Ingredient	Bimatoprost
Dosage Form	Solution
Route	ophthalmic
Strength	0.01%; 0.03%; 0.03
Market Status	Tentative Approval
Company	Apotex; Sandoz

2 of 6
Drug Name	Latisse
PubMed Health	Bimatoprost (Into the eye)
Drug Classes	Antiglaucoma, Ophthalmologic Agent
Drug Label	LATISSE (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 Ingredient	Bimatoprost
Dosage Form	Solution/drops
Route	Topical
Strength	0.03%
Market Status	Prescription
Company	Allergan

3 of 6
Drug Name	Lumigan
Drug Label	LUMIGAN 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 Ingredient	Bimatoprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.01%
Market Status	Prescription
Company	Allergan

4 of 6
Drug Name	Bimatoprost
PubMed Health	Bimatoprost (Into the eye)
Drug Classes	Antiglaucoma, Ophthalmologic Agent
Drug Label	LATISSE (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 Ingredient	Bimatoprost
Dosage Form	Solution
Route	ophthalmic
Strength	0.01%; 0.03%; 0.03
Market Status	Tentative Approval
Company	Apotex; Sandoz

5 of 6
Drug Name	Latisse
PubMed Health	Bimatoprost (Into the eye)
Drug Classes	Antiglaucoma, Ophthalmologic Agent
Drug Label	LATISSE (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 Ingredient	Bimatoprost
Dosage Form	Solution/drops
Route	Topical
Strength	0.03%
Market Status	Prescription
Company	Allergan

6 of 6
Drug Name	Lumigan
Drug Label	LUMIGAN 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 Ingredient	Bimatoprost
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.01%
Market Status	Prescription
Company	Allergan

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.

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