CAS No.130209-82-4,Latanoprost Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	130209-82-4
Name:	Latanoprost
Article Data:	48

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

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

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

: 41639-83-2
latanoprost acid

: 67-63-0
isopropyl alcohol

: 130209-82-4
latanoprost

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;

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

: 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;

: 75-30-9
2-iodo-propane

: 41639-83-2
latanoprost acid

: 130209-82-4
latanoprost

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%

: C39H46O7

: 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%

: 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

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

: 75-30-9
2-iodo-propane

: C23H32O4

: 130209-82-4
latanoprost

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

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

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

...Expand

Raw Materials

67-63-0

Downstream Products

41639-83-2

Total:225 Page 1 of 6 1 2 3 4 5 6 Next>>

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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.

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.