a prostaglandin F2a analogue Latanoprost ophthalmic solution Side effects Product description Molecular Structure Adverse reactions and side effects Chemical Properties Uses Production method
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Latanoprost

a prostaglandin F2a analogue Latanoprost ophthalmic solution Side effects Product description Molecular Structure Adverse reactions and side effects Chemical Properties Uses Production method
Product Name
Latanoprost
CAS No.
130209-82-4
Chemical Name
Latanoprost
Synonyms
17-PHENYL-13,14-DIHYDRO TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER;Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate;xa41;Xalata;phxa41;Latanopros;LATANOPROST;LATANAPROST;Latanoprost>Latanoprost CAS
CBNumber
CB1208384
Molecular Formula
C26H40O5
Formula Weight
432.59
MOL File
130209-82-4.mol
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Latanoprost Property

alpha 
D20 +31.57° (c = 0.91 in acetonitrile)
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
pka
14.84±0.70(Predicted)
color 
pale yellow
Merck 
14,5376
BCS Class
2
InChIKey
GGXICVAJURFBLW-RDSJPUOVSA-N
CAS DataBase Reference
130209-82-4(CAS DataBase Reference)
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Safety

WGK Germany 
3
RTECS 
MJ9669550
HS Code 
2937500000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L1167
Product name
Latanoprost
Purity
≥98% (HPLC)
Packaging
1mg
Price
$176
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR1884
Product name
Latanoprost
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
50mg
Price
$1020
Updated
2024/03/01
Sigma-Aldrich
Product number
1357475
Product name
Latanoprost
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
50mg
Price
$3410
Updated
2024/03/01
TCI Chemical
Product number
L0262
Product name
Latanoprost
Purity
>98.0%(HPLC)
Packaging
10mg
Price
$248
Updated
2024/03/01
TCI Chemical
Product number
L0262
Product name
Latanoprost
Purity
>98.0%(HPLC)
Packaging
50mg
Price
$863
Updated
2024/03/01
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Latanoprost Chemical Properties,Usage,Production

a prostaglandin F2a analogue

Latanoprost is a prostaglandin F2a analogue.It is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor.
It is used to treat certain kinds of glaucoma(open-angle glaucoma ocular hypertension). It is also used to treat a condition called hypertension of the eye. Latanoprost is used to increase the natural outflow of fluid (aqueous humor) from inside the eye into the bloodstream. It appears to work by increasing the outflow of fluid from the eye. This lowers the pressure in the eye.
Latanoprost may make your eyesight blurred for a short length of time. if this happens do not drive or operate machine or use any tools until your eye sight becomes clear again.

Latanoprost ophthalmic solution

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.For the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Latanoprost ophthalmic solution contain a preservative called benzalkonium chloride which can be absorbed onto the surface of contact lenses and may discolour soft contact lenses.

Side effects

Between 6% and 10% (between 1 in 20 and 1 in 6) of persons receiving latanoprost for 6 months report at least one side effect localized to the eyes. These side effects included Temporary blurred vision after application, eyelid redness, permanently darken eyelashes,Swelling or erosions of the cornea,a sensation of a foreign body, discoloration of the iris, itching, a temporary burning sensation during use, and stinging. Discoloration of the iris begins happens slowly. It is caused by an increase in the amount of brown pigment in the iris and may be permanent. Other side effects which have been reported less frequently include dryness of the eyes, increased tearing, herpes simplex keratitis, eye pain and other eye-related discomfort.

Product description

Latanoprost is a novel anti-glaucoma drugs which is suitable for the treatment of primary open-angle glaucoma or the tropical treatment of patients of ocular hypertension which is difficult to be treated and tolerated. It also has excellent efficacy in treating pigment dispersion glaucoma, angle recession, chronic angle-closure glaucoma, uveitis and quiescent exfoliation syndrome but is invalid for treating of uveitis in its active stage.
Latanoprost is a kind of prostaglandin F2α derivative and is a kind of selective F2α receptor agonist. It is a non-active substance but can quickly penetrate into the cornea. It can be hydrolyzed into active free acid in the cornea and the plasma. It can increase the outflow amount of aqueous chambers water through the corner keratin layer. It only needs a small dose has a significant effect in boosting the outflow amount of the aqueous chambers water. The drug liquid can penetrate into the eyeball eyelashes suprachoroidal with excellent intraocular pressure lowering effect. Glaucoma will also clear the clogged trabecular mesh of patients.

Molecular Structure

Latanoprost contains a pentene ring which has α-and ω-carbon chain with the ester of the α-carbon chain termini in the structure can facilitate its penetration through the cornea. At the corneal stroma, latanoprost can be decomposed into free acid which can bind to the FP receptor as the active part. It has hydroxyl group in C15, and has a short ω-chain and a benzene ring which are important for the efficacy of the drug.

Adverse reactions and side effects

Topical administration can result in mild to moderate conjunctival or scleral hyperemia.
Occasionally slight redness on eyes can be observed.
During the treatment of the first 2-3 days, the eyes will have a slight foreign body sensation; a small number of patients may get rash.

Chemical Properties

It is a kind of colorless oil. [α] D20 + 31.57 ° (C = 0.91, acetonitrile).

Uses

It can be used for the treatment of glaucoma.

Production method

First dissolve the compound (Ⅰ) in toluene, cool to 18 °C, further add dicyclohexyl carbodiimide (DCC) and phosphoric acid, followed by addition of (4-phenyl-3-oxobutyl) triphenylphosphonium iodide with condensation being converted to compound (II) which is further converted to the product through the six-step reaction.

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 PGF, 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.

Chemical Properties

Light Yellow Thick Oil

Originator

Pharmacia & pjohn (UK)

Uses

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.

Uses

Prostanoid receptor ligand

Uses

antifungal polyene macrolide that is active in the cell membrane soluble 5% Acetic acid

Uses

Prostaglandin analog, used to treat glaucoma and other degenerative diseases of the eye.

Definition

ChEBI: A prostaglandin Falpha that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension.

Manufacturing Process

Manufacturing process for Latanoprost includes these steps as follows: Synthesis of [3aR-[3aα,4α(E),5β,6aα]]-5-(benzoyloxy) hexahydro-4-(3-oxo-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]-5-(benzoyloxy)hexahydro- 4-(3 -hydroxy-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]- 5-(benzoyloxy)hexahydro-4-(3-hydroxy-5-phenyl-1-pentyl)-2Hcyclopenta[b]furan-2-one, synthesis of 2-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5- phenylpentyl]cyclopentyl]acetic acid, synthesis of [3aR-[3aα,4α(R),5β,6aα]]-hexahydro-5-hydroxy-4-(3-hydroxy-5- phenylpentyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4α(R),5β,6aα]]- hexahydro-5-hydroxy-4-(3-hydroxy-5-phenylpentyl)-2H-cyclopenta[b]furan-2-one;synthesis of (3aR,4R,5R,6aS)-5- (1-ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2Hcyclopenta[b]furan-2-ol;synthesis of 7-[(1R,2R,3R,5S)-3-(1-ethoxyethoxy)-5- hydroxy-2-[(3R)-3-(1-ethoxyethoxy)-5- phenylpentyl]cyclopentyl-5-heptenoic acid; synthesis of (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5- phenylpentyl]cyclopentyl]-5-heptenoic acid (Latanoprost Acid); At last, Latanoprost acid is dissolved in DMF (10 mL) and added to a slurry of cesium carbonate (1.6 g) in DMF (10 mL). 2-Iodopropane (0.49 mL) is added and the slurry is heated to 45°C for about 6 hours. When the reaction is complete, MTBE (40 mL) and water (50 mL) are added and the mixture is stirred for 15 min. The phases are separated and the aqueous phase is washed with MTBE (20 mL). The organic phases are combined and concentrated. The concentrate is chromatographed (silica gel) eluting with MTBE. The appropriate fractions are pooled and concentrated to give (5Z)-(9CI)-7-[(1R,2R,3R,5S)-3,5- Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl ]cyclopentyl]-5-heptenoic acid 1- methylethyl ester (Latanoprost).

brand name

Xalatan (Pharmacia & Upjohn).

Therapeutic Function

Antiglaucoma

General Description

Latanoprost (Xalatan) is available as a 0.005% sterileophthalmic solution in a 2.5-mL dispenser bottle.Latanoprost is also marketed as a combination ophthalmicproduct with the β-adrenergic blocking agent, timolol,which apparently enhances IOP-lowering by decreasing theproduction of aqueous humor. Cautions and side effects aresimilar to those for other ophthalmic prostanoids.

Biochem/physiol Actions

Latanoprost is a potent, selective prostaglandin F2α?analog receptor agonist. It is hydrolyzed by esterases into its biologically active form latanoprost acid in the cornea. Latanoprostplays a role in reducing the intraocular pressure (IOP) due to which it has therapeutic effects in treating glaucoma.

Safety Profile

A poison by ingestion and intravenous route. Human systemic effects. When heated to decomposition it emits acrid smoke and irritating vapors.

Latanoprost Preparation Products And Raw materials

Raw materials

Preparation Products

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Latanoprost Suppliers

Chemvon Biotechnology Co., Ltd
Tel
021-50790412
Fax
+86-21-50790419
Email
info@chemvon.com
Country
China
ProdList
371
Advantage
57
Shanghai Genriver Pharmaceutical Co., Ltd.
Tel
21-13482015261-883 13482015261
Fax
+86-21-37782903
Email
info@genriverpharm.com
Country
China
ProdList
444
Advantage
58
Taizhou KEDE Chemical Co., Ltd
Tel
0576-84613060 13093829633
Fax
0576-84613060
Email
sales@kedechemical.com
Country
China
ProdList
298
Advantage
60
Shanghai finete Pharmaceutical Co., Ltd.
Tel
021-021-00000000 18221039705
Fax
QQ:17263424
Email
finetechpharm@126.com
Country
China
ProdList
208
Advantage
58
Hubei XinghengKang Chemical Technology Co., Ltd.
Tel
027-88878869 18162384755
Fax
027-88878869
Email
xhkhu2014@163.com
Country
China
ProdList
239
Advantage
58
Tianjin Keluo Pharmaceutical Technology Co. LTD
Tel
022-23869539 18920052327
Fax
022-83711180
Email
281258989@qq.com
Country
China
ProdList
61
Advantage
58
Wuhan Sunrise Technology Development Co., Ltd.
Tel
27-027-83314682 13554138826
Fax
+86 (27) 8331-4682
Email
whsrtech@vip.163.com
Country
China
ProdList
219
Advantage
62
GUANGZHOU TOPWORK CHEMISTRY CO.,LTD.
Tel
020-87317062 13048089691
Email
852378519@qq.com
Country
China
ProdList
155
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
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View Lastest Price from Latanoprost manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Latanoprost 130209-82-4
Price
US $0.00/g
Min. Order
1g
Purity
98.5%min
Supply Ability
100g
Release date
2021-07-21
Sinoway Industrial co., ltd.
Product
Latanoprost 130209-82-4
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up
Supply Ability
20 tons
Release date
2021-07-13
Wuhan Nutra Biotechnology Co.,Ltd
Product
Latanoprost 130209-82-4
Price
US $0.00-0.00/g
Min. Order
100g
Purity
98%
Supply Ability
1t
Release date
2021-05-23

130209-82-4, LatanoprostRelated Search:


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