Lonapalene | CAS#91431-42-4 | 5-lipoxygenase inhibitor

MedKoo Cat#: 461479 | Name: Lonapalene

Description:

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

Lonapalene is a 5-lipoxygenase inhibitor that acts as a a novel nonsteroidal antipsoriatic agent.

Chemical Structure

Lonapalene

CAS#91431-42-4

Theoretical Analysis

MedKoo Cat#: 461479

Name: Lonapalene

CAS#: 91431-42-4

Chemical Formula: C16H15ClO6

Exact Mass: 338.0557

Molecular Weight: 338.74

Elemental Analysis: C, 56.73; H, 4.46; Cl, 10.47; O, 28.34

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lonapalene; RS-43179; RS 43179; RS43179;

IUPAC/Chemical Name

6-chloro-2,3-dimethoxynaphthalene-1,4-diyl diacetate

InChi Key

IFWMVQUGSGWCRP-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H15ClO6/c1-8(18)22-13-11-6-5-10(17)7-12(11)14(23-9(2)19)16(21-4)15(13)20-3/h5-7H,1-4H3

SMILES Code

COC1=C(OC)C(OC(C)=O)=C2C=CC(Cl)=CC2=C1OC(C)=O

Appearance

Solid powder

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 338.74 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

1: Black AK, Camp RD, Mallet AI, Cunningham FM, Hofbauer M, Greaves MW. Pharmacologic and clinical effects of lonapalene (RS 43179), a 5-lipoxygenase inhibitor, in psoriasis. J Invest Dermatol. 1990 Jul;95(1):50-4. PubMed PMID: 2164070. 2: Lehman PA, Tomlinson RV, Johnson JI, Olerud JE, Akers WA, Franz TJ. Percutaneous absorption and metabolism of lonapalene in psoriatic skin. Pharm Res. 1992 Sep;9(9):1145-51. PubMed PMID: 1409395. 3: Ong JT, Manoukian E. Release of lonapalene from two-phase emulsion-type ointment systems. Pharm Res. 1988 Jan;5(1):16-20. PubMed PMID: 3244603. 4: Gibert C, Vila L, Puig L, Solá J, Moragas JM. Effect of lonapalene on metabolism of exogenous arachidonic acid in human platelets. Skin Pharmacol. 1989;2(2):86-92. PubMed PMID: 2516737. 5: Venuti MC, Loe BE, Jones GH, Young JM. Topical nonsteroidal antipsoriatic agents. 2. 2,3-(Alkylidenedioxy)naphthalene analogues of lonapalene. J Med Chem. 1988 Nov;31(11):2132-6. PubMed PMID: 3141623. 6: Kiang CH, Lee C. High-performance liquid chromatographic determination of the 1,4-diketo and 1,4-diketo-2,3-dihydroxy metabolites of lonapalene in rat urine. J Chromatogr. 1991 Apr 19;565(1-2):339-47. PubMed PMID: 1874876. 7: Berry PW, Tomlinson RV, Bowen JL. Dermal absorption of lonapalene, a new anti-psoriatic drug. Proc West Pharmacol Soc. 1987;30:137-9. PubMed PMID: 3628265. 8: Jones GH, Venuti MC, Young JM, Murthy DV, Loe BE, Simpson RA, Berks AH, Spires DA, Maloney PJ, Kruseman M, et al. Topical nonsteroidal antipsoriatic agents. 1. 1,2,3,4-Tetraoxygenated naphthalene derivatives. J Med Chem. 1986 Aug;29(8):1504-11. PubMed PMID: 3016268. 9: Zhu YI, Stiller MJ. Preview of potential therapeutic applications of leukotriene B4 inhibitors in dermatology. Skin Pharmacol Appl Skin Physiol. 2000 Sep-Oct;13(5):235-45. Review. PubMed PMID: 10940813. 10: Bosman B. Testing of lipoxygenase inhibitors, cyclooxygenase inhibitors, drugs with immunomodulating properties and some reference antipsoriatic drugs in the modified mouse tail test, an animal model of psoriasis. Skin Pharmacol. 1994;7(6):324-34. PubMed PMID: 7946375. 11: Tramposch KM, Zusi FC, Marathe SA, Stanley PL, Nair X, Steiner SA, Quigley JW. Biochemical and pharmacological properties of a new topical anti-inflammatory compound, 9-phenylnonanohydroxamic acid (BMY 30094). Agents Actions. 1990 Jun;30(3-4):443-50. PubMed PMID: 2117339. 12: Opas EE, Argenbright LW, Humes JL. An enzymatic method for distinguishing the stereoisomers of 12-hydroxyeicosatetraenoic acid in human epidermis and psoriatic scale. Br J Dermatol. 1989 Jan;120(1):49-58. PubMed PMID: 2517876. 13: Carlson RP, O'Neill-Davis L, Calhoun W, Datko L, Musser JH, Kreft AF, Chang JY. Effect of a 5-lipoxygenase (5-LO)/cyclooxygenase (CO) inhibitor, WY-47, 288, on cutaneous models of inflammation. Agents Actions. 1989 Mar;26(3-4):319-28. PubMed PMID: 2500009. 14: Fogh K, Iversen L, Herlin T, Kragballe K. Modulation of eicosanoid formation by lesional skin of psoriasis: an ex vivo skin model. Acta Derm Venereol. 1993 Jun;73(3):191-3. PubMed PMID: 8105616. 15: Batt DG. 5-lipoxygenase inhibitors and their anti-inflammatory activities. Prog Med Chem. 1992;29:1-63. Review. PubMed PMID: 1475368. 16: Fogh K, Herlin T, Kragballe K. In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils. Arch Dermatol Res. 1988;280(7):430-6. PubMed PMID: 2849922. 17: Lassus A, Forsstrom S. A dimethoxynaphthalene derivative (RS-43179 gel) compared with 0.025% fluocinolone acetonide gel in the treatment of psoriasis. Br J Dermatol. 1985 Jul;113(1):103-6. PubMed PMID: 3893513.