What Is Latanoprost?

Latanoprost is a novel phenyl substituted propyl ester prostaglandin F2a, which is a selective F2a receptor agonist. It is an inactive substance that quickly penetrates into the cornea, and can be hydrolyzed into an active free acid in the cornea and plasma. It can increase the outflow of aqueous humor through the corneal layer, with a small amount of medication, but promote a large amount of aqueous humor. The medicinal solution can penetrate the upper layer of the ciliary choroid on the eyeball, which has a good effect on reducing intraocular pressure.

Drug Name: Latanoprost
Alias: Latanoprost
Foreign name: Latanoprost

Main indications: Open angle glaucoma, local treatment for patients with high intraocular pressure.
Dosage: Eye drops, 1 drop at a time, preferably on the affected eye at night
Adverse reactions: Occasionally blurred vision, tingling, conjunctival congestion, and sense of guidance.
CAS: 130209-82-4

Latanoprost Basic Information

Chinese name: latanoprost

Chinese alias: latanoprost;

7- [3,5-dihydroxy-2- (3-hydroxy-5-phenylpentyl) -cyclopentane] hept-5-enoic acid isopropyl ester;

[1R- [1 (Z), 2B (R ^^), 3, 5]]-7- [3,5-Dihydroxy-2- (3-hydroxy-5-phenylpentyl) cyclopentyl] -5-heptenoic acid 1-methylethyl ester;

English name: latanoprost

English alias: xa41; XALATAN; Latanoprost; Xalata; LATANAPROST; phxa41; Lata prostaglandin;

CAS number: 130209-82-4

Molecular formula: C ₂₆ H ₄₀ O ₅

Molecular weight: 432.59300

Chemical structure:

As shown on the right

Exact mass: 432.28800

PSA: 86.99000

LogP: 4.18640

Latanoprost physical and chemical properties

Appearance and properties: light yellow oily

Density: 1.093 g / cm ³

Boiling point: 583.8ºC at 760 mmHg

Flash point: 188.3ºC

Refractive index: 1.537

Storage conditions: -20ºC ^[1]

Latanoprost Toxicology Data

Eye and systemic toxicity studies of latanoprost were performed in several animals. In general, latanoprost is well tolerated and has a large safety margin. The clinical ophthalmic dose and systemic toxicity dose are at least 1000 times different. Unanesthetized monkeys received high-dose latanoprost intravenously (approximately 100 times the clinical dose / kg body weight) and observed an increase in respiratory rate, which may reflect transient bronchoconstriction. Latanoprost has no sensitizing properties in animal tests.

In rabbits and monkeys, no ocular toxicity was observed at a dose of 100 meg / eye / day of latanoprost (clinical dose of 1.5 meg / eye / day). But latanoprost causes increased iris pigmentation in monkeys. The mechanism of pigment increase seems to stimulate melanin production in iris melanocytes, but no proliferative changes were observed. Iris pigmentation changes can be permanent. In the long-term ocular toxicity study, the administration of latanoprost 6mcg / eye / day also caused enlarged palpebral fissure, which was reversible and occurred only at doses higher than the clinical dose. This effect has not been observed in humans. Latanoprost was negative in bacterial mutation reversal tests, mouse lymphoma gene mutation tests, and mouse micronucleus tests. Chromosomal abnormalities were observed in an in vitro human lymphocyte test. Prostaglandin F2, a normally present prostaglandin, has also observed a similar effect, suggesting that the effect is common to this class of substances. Regarding the mutagenicity test, irregular DNA synthesis studies in vivo and in vitro were performed in rats, and the results were negative, indicating that latanoprost has no mutagenic effect. Carcinogenicity tests in mice and rats were also negative. Animal tests have not found any effect of latanoprost on male and female fertility. In rat embryo toxicity studies, latanoprost was administered intravenously at doses of 5, 50, and 250 g / kg / day without any embryo toxicity. However, in rabbits, latanoprost doses of 5 g / kg / day or more can cause embryo death. A dose of 5 g / kg / day (approximately 100 times the clinical dose) can cause significant embryonic fetal toxicity, manifested by increased incidence of late absorption and miscarriage and reduced fetal weight.

No teratogenic effects were found. ^[2]

Latanoprost synthesis method

Starting with 3.3a, 4,5,6,6a-hexahydro-2-oxo-4-hydroxymethyl-5- (4-phenylbenzoyloxy) -2H-cyclopentane [b] The starting material was obtained in several steps. ^[2]

Latanoprost related drug label information

Latanoprost classification name

Primary classification: Ophthalmic drugs Secondary classification: Prostaglandin derivatives

English name of latanoprost drug

Latanoprost

Latanoprost drug alias

Saladan, Shilida, Xalatan

Latanoprost drug dosage form

Eye drops: 25ml, containing 50g of this product per ml.

Latanoprost pharmacological action

Latanoprost is a novel phenyl-substituted propyl ester prostaglandin F2, which is a selective F2 receptor agonist. It is an inactive substance that quickly penetrates into the cornea, and can be hydrolyzed into an active free acid in the cornea and plasma. It can increase the outflow of aqueous humor through the corneal layer, with a small amount of medication, but promote a large outflow of aqueous humor, and the liquid can penetrate the upper layer of the choroid of the eyeball, which has a good effect on reducing intraocular pressure. This product can also make the trabecular meshwork mesh structure which is usually blocked by glaucoma patients unobstructed.

Latanoprost pharmacokinetics

This product is hydrolyzed into free acid in the cornea. This free acid diffuses out of the cornea and enters the aqueous humor. It can reach the peak of blood drug in about 2 hours. After 3 to 4 hours, the IOP began to decrease, and the maximum decrease was reached from 8 to 12 hours. The IOP was not increased for 24 hours. The drug is discharged when the aqueous humor flows out, and the half-life is about 2h. Systemic absorption occurs through the conjunctiva or mucous membrane. The absorbed drugs are mainly excreted in the urine after being metabolized by the liver in the blood circulation system.

Latanoprost indication

It is suitable for open-angle glaucoma and local treatment of patients with high intraocular pressure that is difficult to be treated or tolerated with other drugs.

Latanoprost contraindications

1. Pregnant women and lactating women are prohibited. 2. Patients with severe asthma or eye inflammation during congestion are prohibited.

Latanoprost notes

1. Not recommended for children. 2. This product is not suitable for the treatment of closed-angle or congenital glaucoma, pigmented glaucoma, and open-angle glaucoma of pseudolenses. 3. This product has a synergistic effect when used in combination with other anti-glaucoma drugs. Other eye drops used should be used at least 5 minutes apart. 4. Those who wear contact lenses should remove the lens first, and then put on the lens 15 minutes after dropping the medicine.

Latanoprost adverse reactions

This product is usually well tolerated, with occasional blurred vision, burning pain, tingling, conjunctival hyperemia, transient punctate corneal erosion, and foreign body sensation. Some patients also develop brown pigmentation of the iris (7% after 6 months and 16% after 12 months). Increased pigmentation is more common in races with green-brown, blue-gray-brown, or yellow-brown iris, and is rare in pure blue, blue-gray, or green races. This is due to the stimulation of melanin formation, which can stop progressing after stopping the drug, but obviously cannot recover.

Latanoprost usage dosage

Eye drops: 1 drop per day, preferably to the affected eye at night.

Latanoprost drug interactions

(still uncertain)

Latanoprost drug evaluation

Latanoprost is a new class of intraocular pressure lowering drugs developed in recent years and gradually applied to the clinic. Unlike other anti-glaucoma drugs, this product does not change the coefficient of aqueous humor, the production of aqueous humor, and the suprascleral venous pressure, but reduces the intraocular pressure from the uveal scleral pathway and outflow by increasing water resistance. ^[3]