Latanoprost | PHXA41 | XA-41 | CAS#(ethanol solution) | prostaglandin F2α

MedKoo Cat#: 318089 | Name: Latanoprost, ethanol solution

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Latanoprost, also known as PHXA41 and XA34, is a prostaglandin analogue (more specifically an analogue of prostaglandin F2α) that lowers the pressure by increasing the outflow of aqueous fluid from the eyes through the uvealsclearal tract. Latanoprost is an isopropyl ester prodrug, meaning it is inactive until it is hydrolyzed by esterases in the cornea to the biologically active acid. Latanoprost, in pure form, is an oily liquid. For the convenience of use, it is supplied as 200mg / mL in ethanol.

Chemical Structure

Latanoprost, ethanol solution

CAS#130209-82-4 (ethanol solution)

Theoretical Analysis

MedKoo Cat#: 318089

Name: Latanoprost, ethanol solution

CAS#: 130209-82-4 (ethanol solution)

Chemical Formula: C26H40O5

Exact Mass: 432.2876

Molecular Weight: 432.59

Elemental Analysis: C, 72.19; H, 9.32; O, 18.49

Price and Availability

Size	Price	Availability
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 2,050.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 3,950.00	2 Weeks

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Related CAS #

130209-82-4 (free base); 41639-83-2 (acid); 130209-82-4 (ethanol solution)

Synonym

PHXA41; PHXA-41; PHXA 41; XA34; XA-34; XA 34; Latanoprost, Xalatan, Catioprost

IUPAC/Chemical Name

propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

InChi Key

GGXICVAJURFBLW-CEYXHVGTSA-N

InChi Code

InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1

SMILES Code

O=C(OC(C)C)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C[C@@H]1O

Appearance

A solution in ethanol

Purity

>98% (or refer to the Certificate of Analysis), supplied as 200 mg/mL in ethanol

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Latanoprost (PHXA41) is a prostaglandin F2α analogue and an agonist for the FP prostanoid receptor, and lowers intraocular-pressure (IOP).

In vitro activity:

Latanoprost above concentrations of 3.125 mg/l can induce dose- and time-dependent morphological abnormality, growth retardation, viability decline, and plasma membrane permeability elevation of HCS cells. Moreover, latanoprost can arrest the cell cycle of these cells at S phase and induce PS externalization, DNA fragmentation, and apoptotic body formation of the cells. Furthermore, latanoprost can induce activation of caspase-3, -8 and -9; disruption of MTP; downregulation of anti-apoptotic Bcl-2; upregulation of pro-apoptotic Bax; and cytoplasmic cytochrome c release. Reference: Curr Eye Res. 2017 Apr;42(4):534-541. https://pubmed.ncbi.nlm.nih.gov/27749098/

In vivo activity:

Continuous subcutaneous infusion of latanoprost gradually decreased the IOP (intraocular pressure); the stable nadir of IOP, which was 20% lower than that prior to the start of infusion, was reached on day 3. Subcutaneous continuous delivery of latanoprost decreased the IOP in the conscious normotensive Wistar rats in this study. Reference: Ophthalmol Ther. 2020 Sep;9(3):1-8. https://pubmed.ncbi.nlm.nih.gov/32383108/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	231.16
	Ethanol	100.0	231.16
	Water	100.0	231.16

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Shen JW, Shan M, Peng YY, Fan TJ. Cytotoxic Effect of Latanoprost on Human Corneal Stromal Cells in vitro and its Possible Mechanisms. Curr Eye Res. 2017 Apr;42(4):534-541. doi: 10.1080/02713683.2016.1225770. Epub 2016 Oct 17. PMID: 27749098. 2. Smedowski A, Paterno JJ, Toropainen E, Sinha D, Wylegala E, Kaarniranta K. Excipients of preservative-free latanoprost induced inflammatory response and cytotoxicity in immortalized human HCE-2 corneal epithelial cells. J Biochem Pharmacol Res. 2014 Dec 1;2(4):175-184. PMID: 25530926; PMCID: PMC4270205. 3. Świątkiewicz M, Wełniak-Kamińska M, Fiedorowicz M, Kamińska A, Rejdak R, Grieb P. Peripheral Latanoprost Administration Lowers Intraocular Pressure in the Wistar Rat. Ophthalmol Ther. 2020 Sep;9(3):1-8. doi: 10.1007/s40123-020-00256-8. Epub 2020 Aug 5. PMID: 32383108; PMCID: PMC7406633. 4. Yang Y, Huang C, Lin X, Wu Y, Ouyang W, Tang L, Ye S, Wang Y, Li W, Zhang X, Liu Z. 0.005% Preservative-Free Latanoprost Induces Dry Eye-Like Ocular Surface Damage via Promotion of Inflammation in Mice. Invest Ophthalmol Vis Sci. 2018 Jul 2;59(8):3375-3384. doi: 10.1167/iovs.18-24013. PMID: 30025085.

In vitro protocol:

In vivo protocol:

1. Świątkiewicz M, Wełniak-Kamińska M, Fiedorowicz M, Kamińska A, Rejdak R, Grieb P. Peripheral Latanoprost Administration Lowers Intraocular Pressure in the Wistar Rat. Ophthalmol Ther. 2020 Sep;9(3):1-8. doi: 10.1007/s40123-020-00256-8. Epub 2020 Aug 5. PMID: 32383108; PMCID: PMC7406633. 2. Yang Y, Huang C, Lin X, Wu Y, Ouyang W, Tang L, Ye S, Wang Y, Li W, Zhang X, Liu Z. 0.005% Preservative-Free Latanoprost Induces Dry Eye-Like Ocular Surface Damage via Promotion of Inflammation in Mice. Invest Ophthalmol Vis Sci. 2018 Jul 2;59(8):3375-3384. doi: 10.1167/iovs.18-24013. PMID: 30025085.

1: Sanford M. Preservative-free latanoprost eye drops in patients with primary open-angle glaucoma/ocular hypertension. Clin Drug Investig. 2014 Jul;34(7):521-8. doi: 10.1007/s40261-014-0203-4. Review. PubMed PMID: 24895141. 2: Lou H, Zong Y, Ge YR, Cheng JW, Wei RL. Efficacy and tolerability of latanoprost compared with timolol in the treatment of patients with chronic angle-closure glaucoma. Curr Med Res Opin. 2014 Jul;30(7):1367-73. doi: 10.1185/03007995.2014.905825. Epub 2014 Mar 27. Review. PubMed PMID: 24641069. 3: Alm A. Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014. Review. PubMed PMID: 25328381; PubMed Central PMCID: PMC4196887. 4: Konstas AG, Mocan MC, Katsanos A, Voudouragkaki IC, Irkec M. Latanoprost/timolol fixed combination for the treatment of glaucoma. Expert Opin Pharmacother. 2013 Sep;14(13):1815-27. doi: 10.1517/14656566.2013.813482. Epub 2013 Jun 28. Review. PubMed PMID: 23806084. 5: He M, Wang W, Huang W. Efficacy and tolerability of the fixed combinations latanoprost/timolol versus dorzolamide/timolol in patients with elevated intraocular pressure: a meta-analysis of randomized controlled trials. PLoS One. 2013 Dec 11;8(12):e83606. doi: 10.1371/journal.pone.0083606. eCollection 2013. Review. PubMed PMID: 24349536; PubMed Central PMCID: PMC3859645. 6: Digiuni M, Fogagnolo P, Rossetti L. A review of the use of latanoprost for glaucoma since its launch. Expert Opin Pharmacother. 2012 Apr;13(5):723-45. doi: 10.1517/14656566.2012.662219. Epub 2012 Feb 21. Review. PubMed PMID: 22348427. 7: Tressler CS, Wiseman RL, Dombi TM, Jessen B, Huang K, Kwok KK, Wirostko BM. Lack of evidence for a link between latanoprost use and malignant melanoma: an analysis of safety databases and a review of the literature. Br J Ophthalmol. 2011 Nov;95(11):1490-5. doi: 10.1136/bjo.2010.193987. Epub 2011 Apr 21. Review. PubMed PMID: 21515566. 8: Vinuesa-Silva JM, Vinuesa-Silva I, Pinazo-Durán MD, Soto-Alvarez J, Delgado-Ortega L, Díaz-Cerezo S. [Development of conjunctival hyperemia with the use of a fixed combination of latanoprost/timolol: systematic review and meta-analysis of clinical trials]. Arch Soc Esp Oftalmol. 2009 Apr;84(4):199-207. Review. Spanish. PubMed PMID: 19384760. 9: Cheng JW, Li Y, Wei RL. Systematic review of intraocular pressure-lowering effects of adjunctive medications added to latanoprost. Ophthalmic Res. 2009;42(2):99-105. doi: 10.1159/000225963. Epub 2009 Jun 23. Review. PubMed PMID: 19546601. 10: Honrubia F, García-Sánchez J, Polo V, de la Casa JM, Soto J. Conjunctival hyperaemia with the use of latanoprost versus other prostaglandin analogues in patients with ocular hypertension or glaucoma: a meta-analysis of randomised clinical trials. Br J Ophthalmol. 2009 Mar;93(3):316-21. doi: 10.1136/bjo.2007.135111. Epub 2008 Nov 19. Review. PubMed PMID: 19019922; PubMed Central PMCID: PMC2639645. 11: Cheng JW, Wei RL. Meta-analysis of 13 randomized controlled trials comparing bimatoprost with latanoprost in patients with elevated intraocular pressure. Clin Ther. 2008 Apr;30(4):622-32. Review. PubMed PMID: 18498911. 12: Stewart WC, Stewart JA, Mychaskiw MA. Cost-effectiveness of latanoprost and timolol maleate for the treatment of glaucoma in Scandinavia and the United Kingdom, using a decision-analytic health economic model. Eye (Lond). 2009 Jan;23(1):132-40. Epub 2007 Aug 24. Review. PubMed PMID: 17721497. 13: Fung AT, Reid SE, Jones MP, Healey PR, McCluskey PJ, Craig JC. Meta-analysis of randomised controlled trials comparing latanoprost with brimonidine in the treatment of open-angle glaucoma, ocular hypertension or normal-tension glaucoma. Br J Ophthalmol. 2007 Jan;91(1):62-8. Epub 2006 Sep 6. Review. PubMed PMID: 16956912; PubMed Central PMCID: PMC1857560. 14: Simmons ST, Dirks MS, Noecker RJ. Bimatoprost versus latanoprost in lowering intraocular pressure in glaucoma and ocular hypertension: results from parallel-group comparison trials. Adv Ther. 2004 Jul-Aug;21(4):247-62. Review. PubMed PMID: 15605619. 15: Feldman RM. An evaluation of the fixed-combination of latanoprost and timolol for use in open-angle glaucoma and ocular hypertension. Expert Opin Pharmacother. 2004 Apr;5(4):909-21. Review. PubMed PMID: 15102573. 16: Costagliola C, Parmeggiani F, Sebastiani A. Assessing the cost-effectiveness of switching from a beta-blocker to latanoprost in the treatment of ocular hypertension. Expert Opin Pharmacother. 2003 Oct;4(10):1775-88. Review. PubMed PMID: 14521487. 17: Perry CM, McGavin JK, Culy CR, Ibbotson T. Latanoprost : an update of its use in glaucoma and ocular hypertension. Drugs Aging. 2003;20(8):597-630. Review. PubMed PMID: 12795627. 18: Ravinet E, Mermoud A, Brignoli R. Four years later: a clinical update on latanoprost. Eur J Ophthalmol. 2003 Mar;13(2):162-75. Review. PubMed PMID: 12696636. 19: Bron AM, Emmerich KH. Latanoprost versus combined timolol and dorzolamide. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S148-54. Review. PubMed PMID: 12204712. 20: Higginbotham EJ, Diestelhorst M, Pfeiffer N, Rouland JF, Alm A. The efficacy and safety of unfixed and fixed combinations of latanoprost and other antiglaucoma medications. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S133-40. Review. PubMed PMID: 12204710.