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Basic Information
| CAS No.: | 130209-82-4 |
|---|---|
| Name: | Latanoprost |
| Molecular Structure: | |
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| Formula: | C26H40O5 |
| Molecular Weight: | 432.601 |
| 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); |
| EINECS: | 634-172-9 |
| Density: | 1.093 g/cm3 |
| Boiling Point: | 583.8 °C at 760 mmHg |
| Flash Point: | 188.3 °C |
| Solubility: | Soluble in: DMSO (25 mg/mL); ethanol (25 mg/mL) |
| Appearance: | pale yellow oil |
| PSA: | 86.99000 |
| LogP: | 4.18640 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 14h; | A n/a B 99.83% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| 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; |
- 130209-82-4
latanoprost
Conditions
| Conditions | Yield |
|---|---|
| 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; |
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
- 130209-82-4
latanoprost
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| 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
C
- 130209-82-4
latanoprost
Conditions
| Conditions | Yield |
|---|---|
| Purification / work up; | A n/a B n/a C 45% |
...Expand
Raw Materials
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Latanoprost
Chemistry
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:
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.
XALATAN is also a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.
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
Safety Profile
A poison by ingestion and intravenous route. Human systemic effects. When heated to decomposition it emits acrid smoke and irritating vapors.