Latanoprost
Synonym(s):Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate;Isopropyl (5Z,9α,11α,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate;Latanoprost;Xalatan
- CAS NO.:130209-82-4
- Empirical Formula: C26H40O5
- Molecular Weight: 432.59
- MDL number: MFCD00216074
- EINECS: 634-172-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-12-13 13:45:59
What is Latanoprost?
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.
Toxicity
The oral LD50 in the rat is > 50 mg/kg.
An overdose of latanoprost is not expected to result in dangerous patient outcomes, however, conjunctival or episcleral hyperemia may occur. An intravenous infusion of 3 μg/kg of latanoprost in healthy volunteers led to mean plasma concentrations 200 times higher than a normally administered therapeutic dose and no adverse effects were noted. One study suggested that an overdose of latanoprost leads to cystoid macular edema after a large, unintended overdose. This resolved within 4 weeks after 4 weeks following treatment with nepafenac 0.3% eye drops in addition to oral acetazolamide. Contact the local poison control center for updated guidance on managing a latanoprost overdose.
Description
Xalatan was launched in Sweden, Switzerland and the US for the treatment of glaucoma. It can be synthesized, from the Corey lactone, using standard prostaglandin chemistry. Latanoprost is a PGF2α, analog that is more lipophilic thus is better able to penetrate the cornea. The (15R)-diastereomer has only 10% of the activity compared to the (15S)-diastereomer. It is a selective FP receptor agonist with little or no effect on the other prostanoid receptors. The antiglaucoma effects are the result of reduced intraocular pressure arising by increasing uveoscleral outflow with little or no effect on trabeculo-canalicular aqueous outflow and no effect on retinal vasculation or permeability of the blood-aqueous barrier. The topical application is sufficient for a single daily dosage and is well tolerated with no detectible conjunctival hyperaemia.
The Uses of Latanoprost
Latanoprost is the isopropyl ester of 17-phenyl-13,14-dihydro prostaglandin F2α (17-phenyl-13,14-dihydro PGF2α). It is a prodrug form of the free acid, which is a potent agonist of the FP receptor in the eye. Latanoprost reduces intraocular pressure in glaucoma patients with few side effects. The EC50 value of latanoprost (tested as the free acid) for FP receptors is 3.6 nM.
Indications
Latanoprost is indicated for the reduction of elevated intraocular pressure in patients who have been diagnosed with open-angle glaucoma or ocular hypertension. It is available as monotherapy or in a combination product with netarsudil or timolol.
In Canada, latanoprost is also indicated to treat elevated intraocular pressure due to angle-closure glaucoma that has been treated with peripheral iridotomy or laser iridoplasty.
Background
Latanoprost is a prodrug analog of prostaglandin F2 alpha that is used to treat elevated intraocular pressure (IOP). It was initially approved by the FDA in 1998. Latanoprost is the first topical prostaglandin F2 alpha analog used for glaucoma treatment. It has been found to be well-tolerated and its use does not normally result in systemic adverse effects like other drugs used to treat elevated intraocular pressure, such as Timolol. Another benefit latanoprost is that it can be administered once a day.
What are the applications of Application
Latanoprost is a prodrug of 17-phenyl-13,14-dihydro prostaglandin F2α
Pharmacokinetics
Latanoprost effectively decreases intraocular pressure by increasing uveoscleral outflow. A decrease in intraocular pressure has been measured within 3–4 hours post-administration, reaches a maximum decrease at 8–12 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.
Metabolism
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.
Properties of Latanoprost
Boiling point: | 583.8±50.0 °C(Predicted) |
Density | 1.093±0.06 g/cm3(Predicted) |
storage temp. | -20°C |
solubility | DMSO: freely soluble |
form | oil |
color | pale yellow |
Safety information for Latanoprost
Signal word | Warning |
Pictogram(s) |
Corrosion Corrosives GHS05 Health Hazard GHS08 |
GHS Hazard Statements |
H413:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. |
Computed Descriptors for Latanoprost
InChIKey | GGXICVAJURFBLW-RDSJPUOVSA-N |
Abamectin manufacturer
CHEMAZON LABORATORIES PRIVATE LIMITED
Aptus Therapeutics
Integrum Life Sciences Private Limited
Varanous Labs Pvt Ltd
Honour Lab Limited
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