{"id":16445,"date":"2025-10-21T10:41:51","date_gmt":"2025-10-21T03:41:51","guid":{"rendered":"https:\/\/nhathuocngocanh.com\/bp\/?p=16445"},"modified":"2025-10-21T10:41:51","modified_gmt":"2025-10-21T03:41:51","slug":"latanoprost","status":"publish","type":"post","link":"https:\/\/nhathuocngocanh.com\/bp\/latanoprost\/","title":{"rendered":"Latanoprost"},"content":{"rendered":"

(Ph. Eur. monograph 2230)<\/p>\n

C_{26<\/sub>H_{40<\/sub>O_{5<\/sub>\u00a0 \u00a0 \u00a0 \u00a0432.6\u00a0 \u00a0 \u00a0 \u00a0130209-82-4<\/p>\n}}}

Action and use<\/strong><\/p>\n

Prostaglandin analogue; treatment of intraocular pressure<\/p>\n

DEFINITION<\/h2>\n
Propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate.<\/p>\n
Content<\/h3>\n
94.0 per cent to 102.0 per cent (anhydrous substance).<\/p>\n
CHARACTERS<\/h2>\n
Appearance<\/h3>\n
Clear, colourless or yellow, viscous, oily liquid.<\/p>\n
Solubility<\/h3>\n
Practically insoluble in water, very soluble in acetonitrile, freely soluble in anhydrous ethanol.<\/p>\n
IDENTIFICATION<\/h2>\n
A. Infrared absorption spectrophotometry (2.2.24).<\/p>\n
Comparison: Ph. Eur. reference spectrum of latanoprost.<\/p>\n
B. Specific optical rotation (see Tests).<\/p>\n
TESTS<\/h2>\n
Specific optical rotation (2.2.7)<\/h4>\n
+ 32.0 to + 37.0 (anhydrous substance).<\/p>\n
Dissolve 0.100 g in acetonitrile R and dilute to 10.0 mL with the same solvent.<\/p>\n
Related substances<\/h3>\n
Liquid chromatography (2.2.29). Carry out the test protected from light.<\/p>\n
Test solution: Dissolve 20.0 mg of the substance to be examined in 2 mL of anhydrous ethanol R and dilute to 10.0 mL with heptane R.<\/p>\n
Reference solution (a): Dissolve the contents of a vial of latanoprost for system suitability CRS (containing impurities E and F) in 200 \u03bcL of anhydrous ethanol R then add 800 \u03bcL of heptane R.<\/p>\n
Reference solution (b): Dilute 1.0 mL of the test solution to 100.0 mL with the mobile phase. Dilute 1.0 mL of this solution to 10.0 mL with the mobile phase.<\/p>\n
Reference solution (c): Dissolve 20.0 mg of latanoprost CRS in 2 mL of anhydrous ethanol R and dilute to 10.0 mL with heptane R.<\/p>\n
Column:<\/p>\n
\u2014 size: l = 0.25 m, \u00d8 = 4.6 mm;<\/p>\n
\u2014 stationary phase: silica gel for chromatography R (5 \u03bcm);<\/p>\n
\u2014 temperature: 30 \u00b0C.<\/p>\n
Mobile phase: anhydrous ethanol R, heptane R (6:94 V\/V).<\/p>\n
Flow rate: 1.3 mL\/min.<\/p>\n
Detection: Spectrophotometer at 210 nm.<\/p>\n
Injection: 10 \u03bcL of the test solution and reference solutions (a) and (b).<\/p>\n
Run time: Twice the retention time of latanoprost.<\/p>\n
Identification of impurities: Use the chromatogram supplied with latanoprost for system suitability CRS and the chromatogram obtained with reference solution (a) to identify the peaks due to impurities E and F.<\/p>\n
Relative retention: With reference to latanoprost (retention time = about 16 min): impurity E = about 0.9; impurity F = about 1.1.<\/p>\n
System suitability Reference solution (a):<\/p>\n
\u2014 resolution: minimum 2.0 between the peaks due to latanoprost and impurity F.<\/p>\n
Calculation of percentage contents:<\/p>\n
\u2014 for each impurity, use the concentration of latanoprost in reference solution (b).<\/p>\n
Limits:<\/p>\n
\u2014 impurity F: maximum 3.5 per cent;<\/p>\n
\u2014 impurity E: maximum 0.4 per cent;<\/p>\n
\u2014 unspecified impurities: for each impurity, maximum 0.10 per cent;<\/p>\n
\u2014 sum of impurities other than F: maximum 1.0 per cent;<\/p>\n
\u2014 reporting threshold: 0.05 per cent.<\/p>\n
Impurity H<\/h3>\n
Liquid chromatography (2.2.29).<\/p>\n
Solvent mixture: acetonitrile R, water R (30:70 V\/V).<\/p>\n
Test solution: Dissolve 25.0 mg of the substance to be examined in the solvent mixture and dilute to 25.0 mL with the solvent mixture.<\/p>\n
Reference solution (a): Dissolve the contents of a vial of latanoprost impurity H CRS in 1.0 mL of the solvent mixture.<\/p>\n
Reference solution (b): To 50 \u03bcL of the test solution add 450 \u03bcL of reference solution (a).<\/p>\n
Column:<\/p>\n
\u2014 size: l = 0.15 m, \u00d8 = 4 mm;<\/p>\n
\u2014 stationary phase: base-deactivated end-capped octadecylsilyl silica gel for chromatography R (5 \u03bcm);<\/p>\n
\u2014 temperature: 60 \u00b0C.<\/p>\n
Mobile phase:<\/p>\n
\u2014 mobile phase A: phosphoric acid R, acetonitrile R1, water for chromatography R (0.1:30:70 V\/V\/V);<\/p>\n
\u2014 mobile phase B: phosphoric acid R, water for chromatography R, acetonitrile R1 (0.1:20:80 V\/V\/V);<\/p>\n\n\n\n\n\n\n
Time<\/strong>
\n(min)<\/strong><\/td>\n Mobile phase A<\/strong>
\n(per cent V\/V)<\/strong><\/td>\n Mobile phase B<\/strong>
\n(per cent V\/V)<\/strong><\/td>\n<\/tr>\n
0 – 9<\/td>\n 100<\/td>\n 0<\/td>\n<\/tr>\n
9 – 10<\/td>\n 100 \u2192 0<\/td>\n 0 \u2192 100<\/td>\n<\/tr>\n
10 – 15<\/td>\n 0<\/td>\n 100<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n
Flow rate: 1.0 mL\/min.<\/p>\n
Detection: Spectrophotometer at 200 nm.<\/p>\n
Injection: 50 \u03bcL.<\/p>\n
Identification of impurities: Use the chromatogram obtained with reference solution (a) to identify the peak due to impurity H.<\/p>\n
Relative retention: With reference to latanoprost (retention time = about 12 min): impurity H = about 0.7.<\/p>\n
System suitability: Reference solution (b):<\/p>\n
\u2014 resolution: minimum 5.0 between the peaks due to impurity H and latanoprost.<\/p>\n
Calculation of percentage content:<\/p>\n
\u2014 use the concentration of impurity H in reference solution (a).<\/p>\n
Limit:<\/p>\n
\u2014 impurity H: maximum 0.15 per cent.<\/p>\n
Water (2.5.32)<\/h4>\n
Maximum 0.50 per cent, determined on 0.100 g.<\/p>\n
ASSAY<\/h2>\n
Liquid chromatography (2.2.29) as described in the test for related substances with the following modifications.<\/p>\n
Injection: Test solution and reference solution (c).<\/p>\n
Calculate the percentage content of C_{26<\/sub>H_{40<\/sub>O_{5<\/sub> taking into account the assigned content of latanoprost CRS.<\/p>\n}}}
STORAGE<\/h2>\n
At a temperature of 2 \u00b0C to 8 \u00b0C.<\/p>\n
IMPURITIES<\/h2>\n
Specified impurities E, F, H.<\/p>\n
Other detectable impurities (the following substances would, if present at a sufficient level, be detected by one or other of the tests in the monograph. They are limited by the general acceptance criterion for other\/unspecified impurities and\/or by the general monograph Substances for pharmaceutical use (2034). It is therefore not necessary to identify these impurities for demonstration of compliance. See also 5.10. Control of impurities in substances for pharmaceutical use) A, B, C, D, G, J.<\/p>\n
$\"Latanoprost\"$ <\/p>\n
A. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(3R)-3-(formyloxy)-5-phenylpentyl]-3,5-dihydroxycyclopentyl]hept- 5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
B. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3-(formyloxy)-5-hydroxy-2-[(3R)-3-hydroxy-5-
\nphenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
C. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-5-(formyloxy)-3-hydroxy-2-[(3R)-3-hydroxy-5-
\nphenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
D. propan-2-yl 5-(diphenylphosphoryl)pentanoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
E. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
F. propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
G. methyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
H. (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid,<\/p>\n
$\"Latanoprost\"$ <\/p>\n
J. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(3R)-5-phenyl-3-[(triethylsilyl)oxy]pentyl]-3,5-bis[(triethylsilyl)oxy]cyclopentyl]hept-5-enoate.<\/p>\n","protected":false},"excerpt":{"rendered":"
(Ph. Eur. monograph 2230) C26H40O5\u00a0 \u00a0 \u00a0 \u00a0432.6\u00a0 \u00a0 \u00a0 \u00a0130209-82-4 Action and use Prostaglandin analogue; treatment of intraocular pressure DEFINITION Propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate. Content 94.0 per cent to 102.0 per cent (anhydrous substance). CHARACTERS Appearance Clear, colourless or yellow, viscous, oily liquid. Solubility Practically insoluble in water, very soluble in acetonitrile, freely soluble in anhydrous…<\/p>\n","protected":false},"author":2,"featured_media":16765,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[174],"tags":[],"class_list":["post-16445","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-medicinal-substances"],"acf":[],"_links":{"self":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/comments?post=16445"}],"version-history":[{"count":3,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445\/revisions"}],"predecessor-version":[{"id":16766,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445\/revisions\/16766"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/media\/16765"}],"wp:attachment":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/media?parent=16445"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/categories?post=16445"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/tags?post=16445"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}

Time<\/strong> \n(min)<\/strong><\/td>\n	Mobile phase A<\/strong> \n(per cent V\/V)<\/strong><\/td>\n	Mobile phase B<\/strong> \n(per cent V\/V)<\/strong><\/td>\n<\/tr>\n
0 – 9<\/td>\n	100<\/td>\n	0<\/td>\n<\/tr>\n
9 – 10<\/td>\n	100 \u2192 0<\/td>\n	0 \u2192 100<\/td>\n<\/tr>\n
10 – 15<\/td>\n	0<\/td>\n	100<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n Flow rate: 1.0 mL\/min.<\/p>\n Detection: Spectrophotometer at 200 nm.<\/p>\n Injection: 50 \u03bcL.<\/p>\n Identification of impurities: Use the chromatogram obtained with reference solution (a) to identify the peak due to impurity H.<\/p>\n Relative retention: With reference to latanoprost (retention time = about 12 min): impurity H = about 0.7.<\/p>\n System suitability: Reference solution (b):<\/p>\n \u2014 resolution: minimum 5.0 between the peaks due to impurity H and latanoprost.<\/p>\n Calculation of percentage content:<\/p>\n \u2014 use the concentration of impurity H in reference solution (a).<\/p>\n Limit:<\/p>\n \u2014 impurity H: maximum 0.15 per cent.<\/p>\n Water (2.5.32)<\/h4>\n Maximum 0.50 per cent, determined on 0.100 g.<\/p>\n ASSAY<\/h2>\n Liquid chromatography (2.2.29) as described in the test for related substances with the following modifications.<\/p>\n Injection: Test solution and reference solution (c).<\/p>\n Calculate the percentage content of C_{26<\/sub>H_{40<\/sub>O_{5<\/sub> taking into account the assigned content of latanoprost CRS.<\/p>\n}}} STORAGE<\/h2>\n At a temperature of 2 \u00b0C to 8 \u00b0C.<\/p>\n IMPURITIES<\/h2>\n Specified impurities E, F, H.<\/p>\n Other detectable impurities (the following substances would, if present at a sufficient level, be detected by one or other of the tests in the monograph. They are limited by the general acceptance criterion for other\/unspecified impurities and\/or by the general monograph Substances for pharmaceutical use (2034). It is therefore not necessary to identify these impurities for demonstration of compliance. See also 5.10. Control of impurities in substances for pharmaceutical use) A, B, C, D, G, J.<\/p>\n $\"Latanoprost\"$ <\/p>\n A. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(3R)-3-(formyloxy)-5-phenylpentyl]-3,5-dihydroxycyclopentyl]hept- 5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n B. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3-(formyloxy)-5-hydroxy-2-[(3R)-3-hydroxy-5- \nphenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n C. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-5-(formyloxy)-3-hydroxy-2-[(3R)-3-hydroxy-5- \nphenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n D. propan-2-yl 5-(diphenylphosphoryl)pentanoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n E. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n F. propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n G. methyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate,<\/p>\n $\"Latanoprost\"$ <\/p>\n H. (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid,<\/p>\n $\"Latanoprost\"$ <\/p>\n J. propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(3R)-5-phenyl-3-[(triethylsilyl)oxy]pentyl]-3,5-bis[(triethylsilyl)oxy]cyclopentyl]hept-5-enoate.<\/p>\n","protected":false},"excerpt":{"rendered":" (Ph. Eur. monograph 2230) C26H40O5\u00a0 \u00a0 \u00a0 \u00a0432.6\u00a0 \u00a0 \u00a0 \u00a0130209-82-4 Action and use Prostaglandin analogue; treatment of intraocular pressure DEFINITION Propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate. Content 94.0 per cent to 102.0 per cent (anhydrous substance). CHARACTERS Appearance Clear, colourless or yellow, viscous, oily liquid. Solubility Practically insoluble in water, very soluble in acetonitrile, freely soluble in anhydrous…<\/p>\n","protected":false},"author":2,"featured_media":16765,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[174],"tags":[],"class_list":["post-16445","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-medicinal-substances"],"acf":[],"_links":{"self":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/comments?post=16445"}],"version-history":[{"count":3,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445\/revisions"}],"predecessor-version":[{"id":16766,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/posts\/16445\/revisions\/16766"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/media\/16765"}],"wp:attachment":[{"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/media?parent=16445"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/categories?post=16445"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/nhathuocngocanh.com\/bp\/wp-json\/wp\/v2\/tags?post=16445"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}

Content<\/h3>\n94.0 per cent to 102.0 per cent (anhydrous substance).<\/p>\n

CHARACTERS<\/h2>\n

Appearance<\/h3>\nClear, colourless or yellow, viscous, oily liquid.<\/p>\n

Solubility<\/h3>\nPractically insoluble in water, very soluble in acetonitrile, freely soluble in anhydrous ethanol.<\/p>\n

IDENTIFICATION<\/h2>\nA. Infrared absorption spectrophotometry (2.2.24).<\/p>\nComparison: Ph. Eur. reference spectrum of latanoprost.<\/p>\nB. Specific optical rotation (see Tests).<\/p>\n

TESTS<\/h2>\n

Specific optical rotation (2.2.7)<\/h4>\n+ 32.0 to + 37.0 (anhydrous substance).<\/p>\nDissolve 0.100 g in acetonitrile R and dilute to 10.0 mL with the same solvent.<\/p>\n

Water (2.5.32)<\/h4>\nMaximum 0.50 per cent, determined on 0.100 g.<\/p>\n

STORAGE<\/h2>\nAt a temperature of 2 \u00b0C to 8 \u00b0C.<\/p>\n

Content<\/h3>\n
94.0 per cent to 102.0 per cent (anhydrous substance).<\/p>\n

Appearance<\/h3>\n
Clear, colourless or yellow, viscous, oily liquid.<\/p>\n

Solubility<\/h3>\n
Practically insoluble in water, very soluble in acetonitrile, freely soluble in anhydrous ethanol.<\/p>\n

IDENTIFICATION<\/h2>\n
A. Infrared absorption spectrophotometry (2.2.24).<\/p>\n
Comparison: Ph. Eur. reference spectrum of latanoprost.<\/p>\n
B. Specific optical rotation (see Tests).<\/p>\n

Specific optical rotation (2.2.7)<\/h4>\n
+ 32.0 to + 37.0 (anhydrous substance).<\/p>\n
Dissolve 0.100 g in acetonitrile R and dilute to 10.0 mL with the same solvent.<\/p>\n

Water (2.5.32)<\/h4>\n
Maximum 0.50 per cent, determined on 0.100 g.<\/p>\n

STORAGE<\/h2>\n
At a temperature of 2 \u00b0C to 8 \u00b0C.<\/p>\n