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Identification
NameLatanoprost
Accession NumberDB00654  (APRD01065)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Latanoprost 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 that works by increasing the outflow of aqueous fluid from the eyes.

It is also known by the brand name of Xalatan manufactured by Pfizer.

Structure
Thumb
Synonyms
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate
Latanoprost
Latanoprostum
PhXA 41
Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate
Xalatan
External Identifiers
  • PHXA 41
  • XA 41
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Latanoprostsolution0.05 mgophthalmicActavis Pharma Company2011-10-13Not applicableCanada
Bl Latanoprostsolution50 mcgophthalmicBausch & Lomb IncNot applicableNot applicableCanada
Gd-latanoprostsolution50 mcgophthalmicGenmed A Division Of Pfizer Canada Inc2011-10-03Not applicableCanada
Jamp-latanoprostsolution50 mcgophthalmicJamp Pharma CorporationNot applicableNot applicableCanada
Latanoprostsolution50 ug/mLophthalmicGreenstone LLC1995-03-20Not applicableUs
Latanoprostsolution50 mcgophthalmicLaboratoire Riva IncNot applicableNot applicableCanada
Latanoprost Ophthalmic Solutionsolution50 mcgophthalmicAlcon Canada IncNot applicableNot applicableCanada
Med-latanoprostsolution50 mcgophthalmicGeneric Medical Partners Inc2015-01-09Not applicableCanada
Mint-latanoprostsolution50 mcgophthalmicMint Pharmaceuticals IncNot applicableNot applicableCanada
PMS-latanoprostsolution50 mcgophthalmicPharmascience Inc2014-10-23Not applicableCanada
Riva-latanoprostsolution50 mcgophthalmicLaboratoire Riva Inc2015-05-11Not applicableCanada
Sandoz Latanoprostsolution50 mcgophthalmicSandoz Canada Incorporated2011-12-06Not applicableCanada
Taro-latanoprostsolution50 mcgophthalmicTaro Pharmaceuticals IncNot applicableNot applicableCanada
Teva-latanoprostsolution50 mcgophthalmicTeva Canada LimitedNot applicableNot applicableCanada
Xalatansolution50 ug/mLophthalmicPharmacia And Upjohn Company Llc1995-03-20Not applicableUs
Xalatansolution50 mcgophthalmicPfizer Canada Inc1997-07-28Not applicableCanada
Xalatansolution50 ug/mLophthalmicDispensing Solutions, Inc.1995-03-20Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-latanoprostsolution50 mcgophthalmicApotex Inc2011-10-03Not applicableCanada
Latanoprostsolution50 ug/mLophthalmicMylan Pharmaceuticals Inc.2011-03-22Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicREMEDYREPACK INC.2013-06-12Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicBausch & Lomb Incorporated2011-03-22Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicRebel Distributors Corp2011-03-22Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicAkorn, Inc.2012-07-01Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicMwi2015-04-08Not applicableUs
Latanoprostsolution50 ug/mLophthalmicSandoz Inc2011-01-07Not applicableUs
Latanoprostsolution50 ug/mLophthalmicAmerican Regent, Inc.2011-08-02Not applicableUs
Latanoprostsolution/ drops50 ug/mLophthalmicPhysicians Total Care, Inc.2011-06-21Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArulatanDr. Gerhard Mann
GaapSophia
Gaap OftenoSophia
GaaxChile
GlaucogesicAtlas
GlaumaxKevelt
GlauprostArrow
HysitePfizer
IopizeSIFI
IoprostFDC
IoptameCadila
KlonaprostKlonal
LanoprostSynpac-Kingdom
LanotanKuk Je
LaprostOftalmi
LatacrisSun-Farm
LataluxJelfa
Latan-OphtalWinzer
LataneauAlapis Pharma
Brand mixtures
NameLabellerIngredients
Act Latanoprost/timololActavis Pharma Company
Apo-latanoprost-timopApotex Inc
Gd-latanoprost/timololGenmed A Division Of Pfizer Canada Inc
Jamp-latanoprost/timololJamp Pharma Corporation
Med-latanoprost-timololGeneric Medical Partners Inc
Mint-latanoprost/timololMint Pharmaceuticals Inc
Mylan-latanoprost/timololMylan Pharmaceuticals Ulc
PMS-latanoprost-timololPharmascience Inc
Sandoz Latanoprost/timololSandoz Canada Incorporated
Teva-latanoprost/timololTeva Canada Limited
XalacomPfizer Canada Inc
SaltsNot Available
Categories
UNII6Z5B6HVF6O
CAS number130209-82-4
WeightAverage: 432.5928
Monoisotopic: 432.28757439
Chemical FormulaC26H40O5
InChI KeyInChIKey=GGXICVAJURFBLW-CEYXHVGTSA-N
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
IUPAC Name
propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
SMILES
CC(C)OC(=O)CCC\C=C/C[[email protected]]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Fatty acid ester
  • Benzenoid
  • Cyclopentanol
  • Monocyclic benzene moiety
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
PharmacodynamicsLatanoprost is an isopropyl ester prodrug which is inactive but which becomes active after hydrolysis to the acid from. Latanoprost opthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.
Mechanism of actionLatanoprost is a prostaglandin F2a analogue. Specifically, Latanoprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and man suggest that the main mechanism of action is increased uveoscleral outflow. Elevated IOP represents a major risk factor for glaucomatous field loss. The higher the level of IOP, the greater the likelihood of optic nerve damage and visual field loss.
Related Articles
AbsorptionLatanoprost is well absorbed through the cornea where the isopropyl ester prodrug is hydrolyzed to the acid form. Peak concentration is reached 2 hrs after topical administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic (none except hydrolysis in the eye). Latanoprost is an isopropyl ester prodrug. It is hydrolyzed by esterases in the cornea to latanoprost acid, which is biologically active. The portion of the latanoprost acid that reaches the systemic circulation is metabolized primarily by the liver to 1,2-dinor and 1,2,3,4-tetranor metabolites by fatty acid beta-oxidation.

Route of eliminationNot Available
Half life17 minutes
Clearance
  • 7 mL/min/kg
ToxicitySymptoms of overdose include bloodshot eyes and eye irritation.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9474
Blood Brain Barrier+0.6512
Caco-2 permeable+0.5337
P-glycoprotein substrateSubstrate0.5728
P-glycoprotein inhibitor INon-inhibitor0.8684
P-glycoprotein inhibitor IINon-inhibitor0.7124
Renal organic cation transporterNon-inhibitor0.8805
CYP450 2C9 substrateNon-substrate0.7819
CYP450 2D6 substrateNon-substrate0.8835
CYP450 3A4 substrateSubstrate0.5947
CYP450 1A2 substrateNon-inhibitor0.8845
CYP450 2C9 inhibitorNon-inhibitor0.7724
CYP450 2D6 inhibitorNon-inhibitor0.8985
CYP450 2C19 inhibitorNon-inhibitor0.7236
CYP450 3A4 inhibitorNon-inhibitor0.7393
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7405
Ames testNon AMES toxic0.8324
CarcinogenicityNon-carcinogens0.9379
BiodegradationNot ready biodegradable0.6353
Rat acute toxicity4.3748 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9071
hERG inhibition (predictor II)Non-inhibitor0.8763
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic0.05 mg
Solutionophthalmic50 ug/mL
Solution/ dropsophthalmic50 ug/mL
Solutionophthalmic
Solutionophthalmic50 mcg
Prices
Unit descriptionCostUnit
Xalatan 0.005% Solution 2.5ml Bottle93.59USD bottle
Xalatan 0.005% eye drops45.06USD ml
Xalatan 0.005 % Solution12.18USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1339132 No1997-07-292014-07-29Canada
US5296504 No1994-03-222011-03-22Us
US6429226 No1992-09-062009-09-06Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
water solubility8 mg/mLNot Available
logP4.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0129 mg/mLALOGPS
logP4.16ALOGPS
logP3.98ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity124.34 m3·mol-1ChemAxon
Polarizability50.71 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Arie Gutman, “Process for the preparation of latanoprost.” U.S. Patent US20030149294, issued August 07, 2003.

US20030149294
General References
  1. Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes]. Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [PubMed:11406947 ]
External Links
ATC CodesS01EE01
AHFS Codes
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (502 KB)
MSDSDownload (21.1 KB)
Interactions
Drug Interactions
Drug
BimatoprostThe risk or severity of intraocular pressure can be increased when Latanoprost is combined with Bimatoprost.
InfliximabThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Infliximab.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Prostaglandin f receptor activity
Specific Function:
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum (By similarity). Isoforms 2 to 7 do not bind PGF2-alpha but are proposed to modulate signaling by participating in variant receptor complexes; heterodimers between isoform 1 and ...
Gene Name:
PTGFR
Uniprot ID:
P43088
Molecular Weight:
40054.1 Da
References
  1. Ota T, Aihara M, Narumiya S, Araie M: The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63. [PubMed:16249494 ]
  2. Nakajima T, Matsugi T, Goto W, Kageyama M, Mori N, Matsumura Y, Hara H: New fluoroprostaglandin F(2alpha) derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull. 2003 Dec;26(12):1691-5. [PubMed:14646172 ]
  3. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
  4. Ocklind A: Effect of latanoprost on the extracellular matrix of the ciliary muscle. A study on cultured cells and tissue sections. Exp Eye Res. 1998 Aug;67(2):179-91. [PubMed:9733584 ]
  5. Maxey KM, Johnson JL, LaBrecque J: The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S34-40. [PubMed:12204699 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Kraft ME, Glaeser H, Mandery K, Konig J, Auge D, Fromm MF, Schlotzer-Schrehardt U, Welge-Lussen U, Kruse FE, Zolk O: The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11. doi: 10.1167/iovs.09-4290. Epub 2009 Dec 17. [PubMed:20019365 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11