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    Synopsis

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    Chemistry

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    Also known as: 130209-82-4, Xalatan, Phxa41, Phxa-41, Xa41, Phxa 41
    Molecular Formula
    C26H40O5
    Molecular Weight
    432.6  g/mol
    InChI Key
    GGXICVAJURFBLW-CEYXHVGTSA-N
    FDA UNII
    8S5FB3XXG8
    Latanoprost
    A prostaglandin F analog used to treat OCULAR HYPERTENSION in patients with GLAUCOMA.
    Latanoprost is a Prostaglandin Analog.
    1 2D Structure

    Latanoprost

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
    2.1.2 InChI
    InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
    2.1.3 InChI Key
    GGXICVAJURFBLW-CEYXHVGTSA-N
    2.1.4 Canonical SMILES
    CC(C)OC(=O)CCCC=CCC1C(CC(C1CCC(CCC2=CC=CC=C2)O)O)O
    2.1.5 Isomeric SMILES
    CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    8S5FB3XXG8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Phxa34

    2. Phxa41

    3. Xalatan

    2.3.2 Depositor-Supplied Synonyms

    1. 130209-82-4

    2. Xalatan

    3. Phxa41

    4. Phxa-41

    5. Xa41

    6. Phxa 41

    7. Xa-41

    8. Latanoprost (isopropyl Ester)

    9. Isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((3r)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate

    10. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

    11. Latanoprost, (+/-)-

    12. 6z5b6hvf6o

    13. 8s5fb3xxg8

    14. Latanoprost, Ethanol Solution

    15. Chebi:6384

    16. Propan-2-yl (5z)-7-{(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate

    17. T-2345

    18. T2345

    19. 5-heptenoic Acid, 7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, 1-methylethyl Ester, (5z)-

    20. Isopropyl (5z,9alpha,11alpha,15r)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprost-5-en-1-oate

    21. Catioprost

    22. (z)-isopropyl 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

    23. 155551-81-8

    24. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl Ester

    25. Smr000466354

    26. Xalatan (tn)

    27. Unii-6z5b6hvf6o

    28. Latanoprostum

    29. Nova-21027

    30. Latanoprost [usan:inn:ban]

    31. Xa 41

    32. Phxa34 [as 15(r,s)-isomer]

    33. Propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

    34. Ar-202

    35. Mfcd00216074

    36. Xelpros

    37. L-ppds

    38. Latanoprost [mi]

    39. Latanoprost [inn]

    40. Latanoprost [jan]

    41. Latanoprost [usan]

    42. Unii-8s5fb3xxg8

    43. Latanoprost [vandf]

    44. Chembl1051

    45. Latanoprost [mart.]

    46. Schembl24698

    47. Latanoprost [usp-rs]

    48. Latanoprost [who-dd]

    49. Mls000759468

    50. Mls001424106

    51. Latanoprost (jan/usp/inn)

    52. Gtpl1961

    53. Dtxsid1041057

    54. Latanoprost [orange Book]

    55. Hms2051h11

    56. Hms2089j17

    57. Hms3715n22

    58. Latanoprost [ep Monograph]

    59. Latanoprost [usp Monograph]

    60. Amy30089

    61. Ex-a1770

    62. Hy-b0577

    63. Xalacom Component Latanoprost

    64. Bdbm50240648

    65. S4709

    66. Zinc12468792

    67. Latanoprost, >=98% (hplc), Oil

    68. Rocklatan Component Latanoprost

    69. Akos024458331

    70. Ccg-100946

    71. Db00654

    72. Nc00196

    73. Latanoprost Component Of Rocklatan

    74. Ncgc00246969-01

    75. Ncgc00246969-06

    76. (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptanoic Acid 1-methylethyl Ester

    77. As-75099

    78. L0262

    79. D00356

    80. Ab00640005-04

    81. Ab00640005-06

    82. 209l824

    83. A806039

    84. Q634959

    85. Sr-01000759428

    86. J-005764

    87. Sr-01000759428-4

    88. Latanoprost, United States Pharmacopeia (usp) Reference Standard

    89. Tris(2,4-dimethylphenyl)phosphine-5,5',5""""-trisulfonic Acid Trisodium Salt

    90. (1r,2r,3r,5s,3''r)-7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)-cyclopentyl]-hept-5-enoic Acid Isopropyl Ester

    91. (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(3r)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid Propan-2-yl Ester

    92. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl Ester, (1r-(1-alpha(z),2-beta(r*),3-alpha,5-alpha))-

    93. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-1-methylethyl Ester, (1r-(1.alpha.(z),2.beta.(r*),3.alpha.,5.alpha.))-

    94. Isopropyl (5z,9alpha,11alpha,15r)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate;xalatan

    95. Propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-bis(oxidanyl)-2-[(3r)-3-oxidanyl-5-phenyl-pentyl]cyclopentyl]hept-5-enoate

    2.4 Create Date
    2005-12-16
    3 Chemical and Physical Properties
    Molecular Weight 432.6 g/mol
    Molecular Formula C26H40O5
    XLogP34.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count14
    Exact Mass432.28757437 g/mol
    Monoisotopic Mass432.28757437 g/mol
    Topological Polar Surface Area87 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity526
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameLatanoprost
    PubMed HealthLatanoprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelLatanoprost is a prostaglandin F2 analogue. Its chemical name is isopropyl-(Z)-7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate. Its molecular formula is C26H40O5 and its chemical structure is:Latanoprost is a...
    Active IngredientLatanoprost
    Dosage FormSolution/drops; Solution
    RouteOphthalmic; ophthalmic
    Strength0.005%
    Market StatusTentative Approval; Prescription
    CompanyAlcon Res; Par Pharm; Bausch And Lomb; Luitpold; Dr Reddys Labs; Mylan; Akorn

    2 of 4  
    Drug NameXalatan
    PubMed HealthLatanoprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelLatanoprost is a prostaglandin F2 analogue. Its chemical name is isopropyl-(Z)-7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate. Its molecular formula is C26H40O5 and its chemical structure is:Latanoprost is a...
    Active IngredientLatanoprost
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.005%
    Market StatusPrescription
    CompanyPharmacia And Upjohn

    3 of 4  
    Drug NameLatanoprost
    PubMed HealthLatanoprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelLatanoprost is a prostaglandin F2 analogue. Its chemical name is isopropyl-(Z)-7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate. Its molecular formula is C26H40O5 and its chemical structure is:Latanoprost is a...
    Active IngredientLatanoprost
    Dosage FormSolution/drops; Solution
    RouteOphthalmic; ophthalmic
    Strength0.005%
    Market StatusTentative Approval; Prescription
    CompanyAlcon Res; Par Pharm; Bausch And Lomb; Luitpold; Dr Reddys Labs; Mylan; Akorn

    4 of 4  
    Drug NameXalatan
    PubMed HealthLatanoprost (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelLatanoprost is a prostaglandin F2 analogue. Its chemical name is isopropyl-(Z)-7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate. Its molecular formula is C26H40O5 and its chemical structure is:Latanoprost is a...
    Active IngredientLatanoprost
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.005%
    Market StatusPrescription
    CompanyPharmacia And Upjohn

    4.2 Drug Indication

    Latanoprost is indicated for the reduction of elevated intraocular pressure in patients who have been diagnosed with open-angle glaucoma or ocular hypertension. Latanoprost may be combined in a product with [Netarsudil], a rho kinase inhibitor, for the same indications. In addition to the above indications, the Canadian monograph for this drug also approves latanoprost for the treatment of elevated intraocular pressure as a result of angle-closure glaucoma that has been treated with peripheral iridotomy or laser iridoplasty.

    FDA Label

    Treatment of glaucoma

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Latanoprost effectively decreases intraocular pressure by increasing uveoscleral outflow. A decrease in intraocular pressure has been measured within 34 hours post-administration, reaches a maximum decrease at 812 hours, and can be maintained for a period of 24 hours. **A note on eye and periorbital changes** Between 3 to 10% of patients taking latanoprost have experienced iris pigmentation after about 3-4 months of latanoprost use. Patients should be notified of this risk before initiating treatment. It may occur in both patients with light-colored irides (green-brown or blue/grey-brown) or dark-colored (brown) irides, but is less pronounced in the latter group. This drug may also cause other ocular effects including infrequent conjunctival hyperemia, pigmentation of periocular tissues, eyelash changes, hypertrichosis, and ocular irritation.

    5.2 MeSH Pharmacological Classification

    Ophthalmic Solutions

    Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    LATANOPROST
    5.3.2 FDA UNII
    6Z5B6HVF6O
    5.3.3 Pharmacological Classes
    Prostaglandins [CS]; Prostaglandin Analog [EPC]
    5.4 ATC Code

    S01EE01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    S - Sensory organs

    S01 - Ophthalmologicals

    S01E - Antiglaucoma preparations and miotics

    S01EE - Prostaglandin analogues

    S01EE01 - Latanoprost

    5.5 Absorption, Distribution and Excretion

    Absorption

    This drug is rapidly absorbed in the cornea as an isopropyl ester prodrug and is then activated by the process of hydrolysis. A small amount of this drug is systemically absorbed. The Cmax of latanoprost in the systemic circulation is reached after 5 minutes and is measured to be 53 pg/mL. The Cmax in the aqueous humor is attained within 2 hours after administration. and has been estimated to be 15-30 ng/mL.

    Route of Elimination

    After hepatic beta-oxidation, the metabolites of latanoprost are primarily found to be excreted by the kidneys. About 88% of the latanoprost dose is recovered in the urine after topical administration. About 15% of a dose is reported to be excreted in the feces.

    Volume of Distribution

    The volume of distribution of latanoprost is 0.16 0.02 L/kg. The activated acid form of latanoprost can be measured in aqueous humor in the initial 4 hours post-administration, and it is measured in the plasma only for 1 hour following ophthalmic administration. This drug is more lipophilic than its parent prostaglandin and easily penetrates the cornea. It has been shown to cross the placenta in rats.

    Clearance

    The systemic clearance of latanoprost is 7 mL/min/kg.

    5.6 Metabolism/Metabolites

    After corneal uptake, this prodrug is hydrolyzed and activated by esterases to become a pharmacologically active drug. The small portion of this drug that is able to reach the circulation is found to be metabolized by the liver to the 1,2-dinor and 1,2,3,4-tetranor metabolites through fatty acid beta-oxidation.

    5.7 Biological Half-Life

    The elimination half-life of latanoprost from the plasma is about 17 minutes. The elimination half-life of latanoprost from the eye is estimated at 23 hours.

    5.8 Mechanism of Action

    Elevated intraocular pressure leads to an increased risk of glaucomatous visual field loss. The higher the intraocular pressure, the higher the risk of damage to the optic nerve and loss of visual field. Latanoprost selectively stimulates the prostaglandin F2 alpha receptor and this results in a decreased intraocular pressure (IOP) via the increased outflow of aqueous humor, which is often implicated in cases of elevated intraocular pressure. Possible specific mechanisms of the abovementioned increased aqueous outflow are the remodeling of the extracellular matrix and regulation of matrix metalloproteinases. These actions result in higher tissue permeability related to humor outflow pathways, which likely change outflow resistance and/or outflow rates.

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    12-Jan-2021
    27-Aug-2024
    GMS
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    DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.005%

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    USFDA APPLICATION NUMBER - 206185

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