Latanoprost acid | CAS#41639-83-2 (acid) | FP receptor agonist

MedKoo Cat#: 330162 | Name: Latanoprost acid

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Description:

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

Latanoprost acid is a potent FP receptor agonist with an EC50 of 3.6 nM for human FP receptors, which is twice the potency of PGF2α. The efficacy of PG analog esters for the treatment of glaucoma correlates closely with the FP receptor binding affinity of the free acid. However, Lat-FA is more irritating and less effective than the prodrug latanoprost when applied directly to the eyes of human glaucoma patients. This product supplied as a solution in methyl acetate

Chemical Structure

Latanoprost acid

CAS#41639-83-2 (acid)

Theoretical Analysis

MedKoo Cat#: 330162

Name: Latanoprost acid

CAS#: 41639-83-2 (acid)

Chemical Formula: C23H34O5

Exact Mass: 390.2406

Molecular Weight: 390.52

Elemental Analysis: C, 70.74; H, 8.78; O, 20.48

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

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

Synonym

Latanoprost acid; Lat-FA; 17-phenyl-13,14-dihydro trinor Prostaglandin F2α; PhXA-85;

IUPAC/Chemical Name

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

InChi Key

HNPFPERDNWXAGS-NFVOFSAMSA-N

InChi Code

InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1

SMILES Code

O[C@@H]1[C@H](C/C=C\CCCC(O)=O)[C@@H](CC[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1

Appearance

liquid

Purity

>98% (or refer to the Certificate of Analysis)

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Latanoprost acid, an analog of prostaglandin (PG) F2α, is an selective prostanoid receptor (FP) agonist that specifically activates the FP-PG receptor.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 390.52 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: Pazderka CW, Oliver B, Murray M, Rawling T. Omega-3 Polyunsaturated Fatty Acid Derived Lipid Mediators and Their Application in Drug Discovery. Curr Med Chem. 2018 Sep 26. doi: 10.2174/0929867325666180927100120. [Epub ahead of print] PubMed PMID: 30259807. 2: Priluck AZ, Havens SJ. Variation in Prostaglandin Analog Prices Paid for Through Medicare Part D. J Glaucoma. 2018 Sep 18. doi: 10.1097/IJG.0000000000001096. [Epub ahead of print] PubMed PMID: 30234751. 3: Inoue K, Shiokawa M, Iwasa M, Ishida K, Tomita G. Short Term Efficacy and Safety of a Latanoprost/Carteolol Fixed Combination Switched from Concomitant Therapy to in Patients with Primary Open-angle Glaucoma or Ocular Hypertension. J Glaucoma. 2018 Sep 18. doi: 10.1097/IJG.0000000000001091. [Epub ahead of print] PubMed PMID: 30234748. 4: Younus M, Schachar RA, Zhang M, Sultan MB, Tressler CS, Huang K, Xu W, Klein M, Platt RW, Mukherjee N, Haenel E, Freedman SF. A Long-term Safety Study of Latanoprost in Pediatric Patients with Glaucoma and Ocular Hypertension: A Prospective Cohort Study. Am J Ophthalmol. 2018 Sep 5. pii: S0002-9394(18)30500-2. doi: 10.1016/j.ajo.2018.08.039. [Epub ahead of print] PubMed PMID: 30194929. 5: Kim DH, Addis VM, Pan W, VanderBeek BL. Comparative Effectiveness of Generic Latanoprost Versus Branded Prostaglandin Analogs for Primary Open Angle Glaucoma. Ophthalmic Epidemiol. 2018 Sep 6:1-9. doi: 10.1080/09286586.2018.1516786. [Epub ahead of print] PubMed PMID: 30188773. 6: Zhao PY, Rahmathullah R, Stagg BC, Almobarak F, Edward DP, Robin AL, Stein JD. A Worldwide Price Comparison of Glaucoma Medications, Laser Trabeculoplasty, and Trabeculectomy Surgery. JAMA Ophthalmol. 2018 Aug 30. doi: 10.1001/jamaophthalmol.2018.3672. [Epub ahead of print] PubMed PMID: 30178000. 7: Xia Y. A red eye induced by a spontaneous carotid cavernous fistula. Am J Emerg Med. 2018 Aug 21. pii: S0735-6757(18)30693-4. doi: 10.1016/j.ajem.2018.08.055. [Epub ahead of print] PubMed PMID: 30170931. 8: Dutca LM, Rudd D, Robles V, Galor A, Garvin MK, Anderson MG. Effects of sustained daily latanoprost application on anterior chamber anatomy and physiology in mice. Sci Rep. 2018 Aug 30;8(1):13088. doi: 10.1038/s41598-018-31280-1. PubMed PMID: 30166564; PubMed Central PMCID: PMC6117323. 9: Erichev VP, Zinina VS. [Latanoprost in hypotensive therapy of glaucoma]. Vestn Oftalmol. 2018;134(4):91-99. doi: 10.17116/oftalma201813404191. Russian. PubMed PMID: 30166517. 10: Park S, Kang S, Lim J, Park E, Nam T, Jeong S, Seo K. Effects of prostaglandin-mediated and cholinergic-mediated miosis on morphology of the ciliary cleft region in dogs. Am J Vet Res. 2018 Sep;79(9):980-985. doi: 10.2460/ajvr.79.9.980. PubMed PMID: 30153051. 11: Aspberg J, Heijl A, Jóhannesson G, Lindén C, Andersson S, Bengtsson B. Intraocular Pressure Lowering Effect of Latanoprost as First-line Treatment for Glaucoma. J Glaucoma. 2018 Aug 14. doi: 10.1097/IJG.0000000000001055. [Epub ahead of print] PubMed PMID: 30113517. 12: Nättinen J, Jylhä A, Aapola U, Parkkari M, Mikhailova A, Beuerman RW, Uusitalo H. Patient stratification in clinical glaucoma trials using the individual tear proteome. Sci Rep. 2018 Aug 13;8(1):12038. doi: 10.1038/s41598-018-30369-x. PubMed PMID: 30104599; PubMed Central PMCID: PMC6089987. 13: Quaranta L, Biagioli E, Riva I, Galli F, Poli D, Rulli E, Katsanos A, Longo A, Uva MG, Oddone F, Torri V, Weinreb RN. The Glaucoma Italian Pediatric Study (GIPSy): Three-year Results. J Glaucoma. 2018 Aug 7. doi: 10.1097/IJG.0000000000001038. [Epub ahead of print] PubMed PMID: 30095601. 14: Aihara M. Response to Novack re: "Pharmacokinetic Analysis of Intraocular Penetration of Latanoprost Solutions with Different Preservatives in Human Eyes". J Ocul Pharmacol Ther. 2018 Jul/Aug;34(6):431. doi: 10.1089/jop.2018.29043.res. PubMed PMID: 30095356. 15: Yip IYM, Raj A. Severe Cutaneous Reaction to Latanoprost Eye Drops. J Ophthalmic Vis Res. 2018 Jul-Sep;13(3):348-350. doi: 10.4103/jovr.jovr_248_16. PubMed PMID: 30090193; PubMed Central PMCID: PMC6058562. 16: Reddy S, Sahay P, Padhy D, Sarangi S, Suar M, Modak R, Rao A. Tear biomarkers in latanoprost and bimatoprost treated eyes. PLoS One. 2018 Aug 6;13(8):e0201740. doi: 10.1371/journal.pone.0201740. eCollection 2018. PubMed PMID: 30080906; PubMed Central PMCID: PMC6078293. 17: Ordóñez JE, Ordóñez A, Osorio UM. Cost-effectiveness analysis of iStent trabecular micro-bypass stent for patients with open-angle glaucoma in Colombia. Curr Med Res Opin. 2018 Aug 10:1-12. doi: 10.1080/03007995.2018.1506022. [Epub ahead of print] PubMed PMID: 30049226. 18: Li QS, Bao FF, Zhang ZY, Ma K. Effect of long-term topical latanoprost medication on conjunctival thickness in patients with glaucoma. Int J Ophthalmol. 2018 Jul 18;11(7):1158-1162. doi: 10.18240/ijo.2018.07.14. eCollection 2018. PubMed PMID: 30046533; PubMed Central PMCID: PMC6048322. 19: Two new drugs for glaucoma. Med Lett Drugs Ther. 2018 Jul 16;60(1551):117-120. PubMed PMID: 30036347. 20: Kaluzhny Y, Kinuthia MW, Truong T, Lapointe AM, Hayden P, Klausner M. New Human Organotypic Corneal Tissue Model for Ophthalmic Drug Delivery Studies. Invest Ophthalmol Vis Sci. 2018 Jun 1;59(7):2880-2898. doi: 10.1167/iovs.18-23944. PubMed PMID: 30025134.