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Latanoprost

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Name

Latanoprost

EINECS 634-172-9
CAS No. 130209-82-4 Density 1.093 g/cm3
PSA 86.99000 LogP 4.18640
Solubility Soluble in: DMSO (25 mg/mL); ethanol (25 mg/mL) Melting Point N/A
Formula C26H40O5 Boiling Point 583.8 °C at 760 mmHg
Molecular Weight 432.601 Flash Point 188.3 °C
Transport Information N/A Appearance pale yellow oil
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 130209-82-4 (Latanoprost) Hazard Symbols N/A
Synonyms

Lata prostaglandin;Latanoprost [USAN:BAN:INN];XA 41;Xalatan (TN);5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1-alpha(Z),2-beta(R*),3-alpha,5-alpha))-;Xalatan;PhXA 41;Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate;Latanoprost (JAN/USAN);

Article Data 48

Latanoprost Synthetic route

75-30-9

2-iodo-propane

41639-83-2

latanoprost acid

A

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

B

130209-82-4

latanoprost

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 14h;A n/a
B 99.83%
41639-83-2

latanoprost acid

67-63-0

isopropyl alcohol

130209-82-4

latanoprost

Conditions
ConditionsYield
With Lipase Novozym 435 at 30℃; for 18h; Enzymatic reaction;92%
Novozym 435 at 30℃; for 18h;92%
With 2-chloro-1,3-dimethyl imidazolium chloride; potassium tert-butylate; triethylamine at 0 - 70℃; for 2h;

isopropyl 11,15-bistetrahydropyranyloxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α

130209-82-4

latanoprost

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In methanol at 52℃; for 4h; Product distribution / selectivity;90%
pyridinium p-toluenesulfonate In methanol at 52℃; for 4h;90%
With pyridinium p-toluenesulfonate In dichloromethane at 40℃; Inert atmosphere;86.1%
With toluene-4-sulfonic acid In isopropyl alcohol at 40℃; for 5h;
With ethanol; pyridinium p-toluenesulfonate at 20 - 50℃; for 3h;
75-30-9

2-iodo-propane

41639-83-2

latanoprost acid

130209-82-4

latanoprost

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;84%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;72%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;68%
856453-33-3

C41H64O8

130209-82-4

latanoprost

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In methanol at 45℃; for 6h; Product distribution / selectivity;83.7%
pyridinium p-toluenesulfonate In methanol at 45℃; for 6h;83.7%

C39H46O7

130209-82-4

latanoprost

Conditions
ConditionsYield
Stage #1: C39H46O7 With hydrogen In ethyl acetate at 20℃; for 4h; Inert atmosphere;
Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 0℃; for 0.5h; Inert atmosphere;
Stage #3: With sodium tetrahydroborate In methanol; dichloromethane; water at 0℃; for 2.5h; Inert atmosphere;
83%
141074-06-8

C26H38O5

130209-82-4

latanoprost

Conditions
ConditionsYield
Stage #1: C26H38O5 With 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride In toluene at -70 - -20℃;
Stage #2: With hydrogenchloride In water; toluene
75%
75-30-9

2-iodo-propane

41639-83-2

latanoprost acid

A

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

B

isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

C

130209-82-4

latanoprost

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 5.5 - 14.2167h; Product distribution / selectivity;A n/a
B n/a
C 63.2%
75-30-9

2-iodo-propane

C23H32O4

130209-82-4

latanoprost

Conditions
ConditionsYield
Stage #1: C23H32O4 With sodium hydride In isopropyl alcohol; mineral oil at 20 - 35℃; for 18h;
Stage #2: 2-iodo-propane With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 18h;
49%
477884-73-4

(3aR,4R,5R,6aS)-hexahydro-5-triethylsilyoxy-4-[5-phenyl-(3R)-3-triethylsilyloxy-pentanyl]-2H-cyclopenta[β]furan-2-one

A

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

B

isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

C

130209-82-4

latanoprost

Conditions
ConditionsYield
Purification / work up;A n/a
B n/a
C 45%

Latanoprost Chemical Properties

Formula: C26H40O5 
Mol. mass :432.593 g/mol
Other name:Latanoprost
XALATAN the brand name of Xalatan manufactured by Pfizer.It is freely soluble in DMSO.
Following is the molecular structure of XALATAN:

Latanoprost Uses

   XALATAN ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension by reducing intraocular pressure.
  XALATAN is also a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.

Latanoprost Toxicity Data With Reference

1.   

ocu-man TDLo:33 µL/kg/25D-I:EYE

   AJOPAA    American Journal of Ophthalmology. 124 (1997),683.
2.   

ocu-man TDLo:99 µL/kg/20W-I:SKN

   AJOPAA    American Journal of Ophthalmology. 124 (1997),544.
3.   

ocu-wmn TDLo:4 nL/kg/5W-I:EYE

   AJOPAA    American Journal of Ophthalmology. 127 (1999),91.
4.   

orl-rat LD50:>50 µg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
5.   

ivn-rat LD50:>2 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
6.   

orl-mus LD50:>50 µg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
7.   

ivn-mus LD50:>2 mg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
8.   

ivn-dog LD50:>680 µg/kg

   YAKUD5    Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.

RTECS : MJ9669550

Latanoprost Safety Profile

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