Latanoprost
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| Systematic (IUPAC) name |
| isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2- [(3R)3-hydroxy-5-phenylpentyl]-cyclopentyl] hept-5-enoate |
| Clinical data |
| Trade names |
Xalatan |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a697003 |
| Pregnancy cat. |
C (US) |
| Legal status |
℞-only (US) |
| Routes |
Topical (eye drops) |
| Pharmacokinetic data |
| Half-life |
17 minutes |
| Identifiers |
| CAS number |
130209-82-4  Y |
| ATC code |
S01EE01 |
| PubChem |
CID 5311221 |
| IUPHAR ligand |
1961 |
| DrugBank |
DB00654 |
| ChemSpider |
4470740 Y |
| UNII |
6Z5B6HVF6O Y |
| KEGG |
D00356 Y |
| ChEBI |
CHEBI:6384 Y |
| ChEMBL |
CHEMBL1051 Y |
| Chemical data |
| Formula |
C26H40O5 |
| Mol. mass |
432.593 g/mol |
| SMILES |
eMolecules & PubChem |
InChI
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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 Y
Key:GGXICVAJURFBLW-CEYXHVGTSA-N Y
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 Y (what is this?) (verify)
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Latanoprost (pronounced la-TA-noe-prost) 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 (more specifically an analogue of prostaglandin F2α1) that works by increasing the outflow of aqueous fluid from the eyes (through the uvealsclearal tract).2
It is also known by the brand name of Xalatan manufactured by Pfizer. Annual sales are approximately $1.6 billion. The patent for latanoprost expired in March 2011, and at least one generic version (manufactured by Mylan Inc.) is now widely available in the U.S.
Latanoprost was developed by Carl B. Camras and his research adviser László Z. Bitó at Columbia University in 1996.3
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Contents
- 1 Adverse reactions
- 2 See also
- 3 References
- 4 External links
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Adverse reactions
Possible side effects:
- May cause reddening of the eyes (hyperemia)
- May cause blurred vision;
- May cause eyelid redness;
- May permanently darken eyelashes;
- May cause eye discomfort;
- May eventually cause permanent darkening of the iris to brown (heterochromia);
- May cause a temporary burning sensation during use.
- May cause thickening of the eyelashes.
- Rarely, herpes simplex keratitis.
- A single case report links latanoprost use to the progression of keratoconus.4
See also
- Bimatoprost, similar structure and effects
- Travoprost
References
- ^ Ishikawa H, Yoshitomi T, Mashimo K, Nakanishi M, Shimizu K (February 2002). "Pharmacological effects of latanoprost, prostaglandin E2, and F2alpha on isolated rabbit ciliary artery". Graefes Arch. Clin. Exp. Ophthalmol. 240 (2): 120–5. doi:10.1007/s00417-001-0412-4. PMID 11931077.
- ^ Patel SS, Spencer CM (1996). "Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension". Drugs Aging 9 (5): 363–378. PMID 8922563.
- ^ http://app1.unmc.edu/publicaffairs/todaysite/sitefiles/today_full.cfm?match=5604
- ^ Amano S, Nakai Y, Ko A, Inoue K, Wakakura M (2008). "A case of keratoconus progression associated with the use of topical latanoprost". Jpn. J. Ophthalmol. 52 (4): 334–6. doi:10.1007/s10384-008-0554-6. ISBN [[Special:BookSources/38400805546|38400805546]]. PMID 18773275.
External links
- LATANOPROST solution [Greenstone LLC] (Nov 2011), Daily Med, U.S. National Library of Medicine, National Institutes of Health
- Xalatan (Pfizer manufacturer)
- Hara T (2001). "Increased iris pigmentation after use of latanoprost in Japanese brown eyes". Nippon Ganka Gakkai Zasshi 105 (5): 314–21. PMID 11406947.
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Ophthalmologicals: antiglaucoma preparations and miotics (S01E)
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| Sympathomimetics |
- Apraclonidine
- Brimonidine (+timolol)
- Clonidine
- Dipivefrine
- Epinephrine
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| Parasympathomimetics |
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muscarinic
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muscarinic/nicotinic
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Acetylcholinesterase inhibitors
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- Demecarium
- Ecothiopate
- Stigmine (Fluostigmine
- Neostigmine
- Physostigmine)
- Paraoxon
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Carbonic anhydrase inhibitors/
(sulfonamides) |
- Acetazolamide
- Brinzolamide (+timolol)
- Diclofenamide
- Dorzolamide (+timolol)
- Methazolamide
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| Beta blocking agents |
- Befunolol
- Betaxolol
- Carteolol
- Levobunolol
- Metipranolol
- Timolol
- Mepindolol
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| Prostaglandin analogues (F2α) |
- Bimatoprost (+timolol)
- Latanoprost (+timolol)
- Tafluprost
- Travoprost (+timolol)
- Unoprostone
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| Other agents |
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anat(g/a/p)/phys/devp/prot
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Autacoids, unsaturated fatty acids: Eicosanoids
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| Precursor |
Arachidonic acid
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| Prostanoids |
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Prostaglandins (PG) and
analogues
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Precursor
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H2
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Active
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D/J
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D2
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E/F
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E2 (Dinoprostone): Enprostil · Sulprostone
E1 (Alprostadil): Misoprostol · Gemeprost
F 2α (Dinoprost): Bimatoprost · Carboprost · Latanoprost · Tafluprost · Travoprost · Unoprostone
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I
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I2 (Prostacyclin/Epoprostenol): Beraprost · Iloprost · Treprostinil
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Thromboxanes (TX)
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A2 · B2
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| Leukotrienes (LT) |
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Precursor
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Arachidonic acid 5-hydroperoxide
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Initial
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A4 · B4
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SRS-A
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C4 · D4 · E4
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| Nonclassic |
Lipoxins (A4, B4) · Virodhamine
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| By function |
bronchoconstriction (PGD2, TXA2, LTC4, LTD4, LTE4)
vasoconstriction (PGF2α, TXA2, TXB2) · vasodilation (PGE2, PGI2, LTC4, LTD4, LTE4)
platelets: induce (TXA2) inhibit (PGD2, PGI2) · leukocytes: induce (TXA2, LTB4) inhibit (PGD2, PGE2)
fever stimulation: (PGE2)
labor stimulation: (PGE 2 (Dinoprostone), PGF 2α (Dinoprost))
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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biochemical families: proteins (amino acids/intermediates) · nucleic acids (constituents/intermediates) · carbohydrates (glycoproteins, alcohols, glycosides)
lipids (fatty acids/intermediates, phospholipids, steroids, sphingolipids, eicosanoids) · tetrapyrroles/intermediates
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