Latanoprost

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Latanoprost
Latanoprost.svg
Latanoprost-3D-balls.png
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 namesXalatan
AHFS/Drugs.commonograph
MedlinePlusa697003
Pregnancy cat.
Legal status
RoutesTopical (eye drops)
Pharmacokinetic data
Half-life17 minutes
Identifiers
CAS number130209-82-4 YesY
ATC codeS01EE01
PubChemCID 5311221
IUPHAR ligand1961
DrugBankDB00654
ChemSpider4470740 YesY
UNII6Z5B6HVF6O YesY
KEGGD00356 YesY
ChEBICHEBI:6384 YesY
ChEMBLCHEMBL1051 YesY
Chemical data
FormulaC26H40O5 
Mol. mass432.593 g/mol
 YesY (what is this?)  (verify)
 
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Latanoprost
Latanoprost.svg
Latanoprost-3D-balls.png
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 namesXalatan
AHFS/Drugs.commonograph
MedlinePlusa697003
Pregnancy cat.
Legal status
RoutesTopical (eye drops)
Pharmacokinetic data
Half-life17 minutes
Identifiers
CAS number130209-82-4 YesY
ATC codeS01EE01
PubChemCID 5311221
IUPHAR ligand1961
DrugBankDB00654
ChemSpider4470740 YesY
UNII6Z5B6HVF6O YesY
KEGGD00356 YesY
ChEBICHEBI:6384 YesY
ChEMBLCHEMBL1051 YesY
Chemical data
FormulaC26H40O5 
Mol. mass432.593 g/mol
 YesY (what is this?)  (verify)

Latanoprost (pronounced la-TAN-oh-prost) ophthalmic solution is a medication administered into the eyes to control the progression of glaucoma or ocular hypertension by reducing intraocular pressure. It is a prostaglandin analogue (more specifically an analogue of prostaglandin F[1]) that lowers the pressure by increasing the outflow of aqueous fluid from the eyes through the uvealsclearal tract.[2] Latanoprost is an isopropyl ester prodrug, meaning it is inactive until it is hydrolyzed by esterases in the cornea to the biologically active acid.[3]

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. The Veterans Health Administration, part of the U.S. Department of Veterans Affairs, uses generic Latanoprost manufactured by Alcon Laboratories of Fort Worth, Texas distributed by Novartis generic brand Sandoz Pharmaceuticals.

Latanoprost was invented by Johan W. Stjernschantz and Bahram Resul, employees of the Pharmacia Corporation of Uppsala, Sweden.[4]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5]

Medical uses[edit]

Ocular hypertension[edit]

Closed-angle glaucoma[edit]

Method of administration[edit]

One drop in the affected eye(s) once daily in the evening; do not exceed the once daily dosage because it has been shown that more frequent administration may decrease the intraocular-pressure (IOP) lowering effect[2]

Adverse effects[edit]

Listed from most to least common:

Concerns related to adverse effects:

Special populations[edit]

Contact lens wearers: Contains benzalkonium chloride which may be absorbed by contact lenses; remove contacts prior to administration and wait 15 minutes before reinserting

Contraindications[edit]

Hypersensitivity to latanoprost, benzalkonium chloride, or any component of the formulation

Drug Interactions[edit]

Bimatoprost: The concomitant use of Latanoprost and Bimatoprost may result in increased intraocular pressure. Risk D: Consider therapy modification

Nonsteroidal Anti-Inflammatory Agents: May diminish the therapeutic effect of Prostaglandins (Ophthalmic). Nonsteroidal Anti-Inflammatory Agents may also enhance the therapeutic effects of Prostaglandins (Ophthalmic). Risk C: Monitor therapy

Pregnancy[edit]

Prescription of Latanoprost is limited in human studies due to high incidence of abortion shown in animal experiments. Because of this, Latanoprost is classified as Risk factor C (Adverse events were observed in animal reproduction studies at maternally toxic doses)according to United States Food and Drug Administration's use-in-pregnancy ratings.[10] Lactation Excretion in breast milk unknown/use caution. Breast-Feeding Considerations It is not known if latanoprost is excreted in breast milk. The manufacturer recommends that caution be exercised when administering latanoprost to nursing women.[2]

Storage[edit]

Latanoprost is a substance exhibiting thermal and solar instability. Concentration of latanoprost will decrease by 10% when stored at 50 and 70 degrees Celsius every 8.25 and 1.32 days respectively. Reaction with ultraviolet radiation will cause rapid degradation of Latanoprost. It is therefor important to store Latanoprost ideally in temperature below room temperature and free from sunlight in order to attain acceptable drug quality. [11]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ a b c 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. doi:10.2165/00002512-199609050-00007. PMID 8922563. 
  3. ^ Huttunen et al. (2011) Prodrugs—from Serendipity to Rational Design. Pharmacol Rev 63:750–771
  4. ^ "Patent US5296504 - Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension - Google Patents". 
  5. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  6. ^ Perry CM, McGavin JK, Culy CR, Ibbotson T (2003). "Latanoprost. An Update of its Use in Glaucoma and Ocular Hypertension". Drugs Aging 20 (8): 1170–2229. PMID 12795627. 
  7. ^ Zhang WY, Wan Po AL, Dua HS, Azuara-Blanco A (2001). "Meta-analysis of randomised controlled trials comparing latanoprost with timolol in the treatment of patients with open angle glaucoma or ocular hypertension". British Journal of Ophthalmology 85: 983–990. doi:10.1136/bjo.85.8.983. PMC 1724079. PMID 11466259. 
  8. ^ Aung T; Wong HT; Yip CC; et al. (2000). "Comparison of the intraocular pressure-lowering effect of latanoprost and timolol in patients with chronic angle closure glaucoma: a preliminary study.". Ophthalmology 107 (6): 1178–83. doi:10.1016/s0161-6420(00)00073-7. PMID 10857840. 
  9. ^ Amano S, Nakai Y, Ko A, Inoue K, Wakakura M (2008). "A case of keratoconus progression associated with the use of topical latanoprost". Japanese Journal of Ophthalmology 52 (4): 334–6. doi:10.1007/s10384-008-0554-6. PMID 18773275. 
  10. ^ De Santis, M., Lucchese, A., Carducci, B., Cavaliere, A., De Santis, L., & Merola, A. et al. (2004). Latanoprost exposure in pregnancy. American Journal Of Ophthalmology, 138(2), 305.pmid=15289149.1
  11. ^ Morgan, P., Proniuk, S., Blanchard, J., & Noecker, R. (2001). Effect of temperature and light on the stability of latanoprost and its clinical relevance. Journal Of Glaucoma, 10(5), 401--405.

External links[edit]