Ralinepag | CAS# 1187856-49-0 | PGI2 agonist

MedKoo Cat#: 319555 | Name: Ralinepag

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Description:

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

Ralinepag (APD-811) is an orally available agonist of the prostacyclin (IP) receptor intended for the treatment of vasospastic diseases such as Pulmonary Arterial Hypertension. Ralinepag has the potential to mimic prostacyclin -- the major product of cyclooxygenase -- in macrovascular endothelium This elicits a potent vasodilation response and inhibition of platelet aggregation when binding to this receptor.

Chemical Structure

Ralinepag

CAS#1187856-49-0 (free base)

Theoretical Analysis

MedKoo Cat#: 319555

Name: Ralinepag

CAS#: 1187856-49-0 (free base)

Chemical Formula: C23H26ClNO5

Exact Mass: 431.1500

Molecular Weight: 431.91

Elemental Analysis: C, 63.96; H, 6.07; Cl, 8.21; N, 3.24; O, 18.52

Price and Availability

Size	Price	Availability
1mg	USD 210.00	2 Weeks
5mg	USD 400.00	2 Weeks
10mg	USD 640.00	2 Weeks
25mg	USD 855.00	2 Weeks

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Related CAS #

1187856-49-0 (free base) 1187857-75-5 (sodium)

Synonym

APD-811; APD 811; APD811; Ralinepag

IUPAC/Chemical Name

2-(((1r,4r)-4-((((4-chlorophenyl)(phenyl)carbamoyl)oxy)methyl)cyclohexyl)methoxy)acetic acid

InChi Key

NPDKXVKJRHPDQT-IYARVYRRSA-N

InChi Code

InChI=1S/C23H26ClNO5/c24-19-10-12-21(13-11-19)25(20-4-2-1-3-5-20)23(28)30-15-18-8-6-17(7-9-18)14-29-16-22(26)27/h1-5,10-13,17-18H,6-9,14-16H2,(H,26,27)/t17-,18-

SMILES Code

O=C(O)COC[C@H]1CC[C@H](COC(N(C2=CC=C(Cl)C=C2)C3=CC=CC=C3)=O)CC1

Appearance

Solid powder

Purity

>95% (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, DMF, and ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, and ethanol

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:

Ralinepag shows no effect on cytochrome P450 enzymes (IC50 > 50 μM for CYPs 1A2, 2D6, 3A4 2C8, 2C9, and 2C19) or hERG channel functional activity in a patch clamp assay (IC50 > 30 μM). Ralinepag also inhibits the ADP-induced human platelet aggregation, with an IC50 of 38 nM. It is a non-prostanoid prostacyclin receptor agonist, with EC50s of 8.5 nM, 530 nM and 850 nM for human and rat IP receptor and human DP1 receptor, respectively.

In vitro activity:

To be determined

In vivo activity:

Ralinepag reduced pulmonary vascular resistance compared with placebo in pulmonary arterial hypertension patients on mono or dual combination background therapy. Reference: Eur Respir J. 2019 Oct 10;54(4):1901030. https://pubmed.ncbi.nlm.nih.gov/31391223/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	23.15
	DMF	15.0	34.73
	Ethanol	10.0	23.15

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 431.91 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. Torres F, Farber H, Ristic A, McLaughlin V, Adams J, Zhang J, Klassen P, Shanahan W, Grundy J, Hoffmann I, Cabell C, Escribano Subías P, Sood N, Keogh A, D'Souza G, Rubin L. Efficacy and safety of ralinepag, a novel oral IP agonist, in PAH patients on mono or dual background therapy: results from a phase 2 randomised, parallel group, placebo-controlled trial. Eur Respir J. 2019 Oct 10;54(4):1901030. doi: 10.1183/13993003.01030-2019. PMID: 31391223. 2. Tran TA, Kramer B, Shin YJ, Vallar P, Boatman PD, Zou N, Sage CR, Gharbaoui T, Krishnan A, Pal B, Shakya SR, Garrido Montalban A, Adams JW, Ramirez J, Behan DP, Shifrina A, Blackburn A, Leakakos T, Shi Y, Morgan M, Sadeque A, Chen W, Unett DJ, Gaidarov I, Chen X, Chang S, Shu HH, Tung SF, Semple G. Discovery of 2-(((1r,4r)-4-(((4-Chlorophenyl)(phenyl)carbamoyl)oxy)methyl)cyclohexyl)methoxy)acetate (Ralinepag): An Orally Active Prostacyclin Receptor Agonist for the Treatment of Pulmonary Arterial Hypertension. J Med Chem. 2017 Feb 9;60(3):913-927. doi: 10.1021/acs.jmedchem.6b00871. Epub 2017 Jan 19. PMID: 28072531.

In vitro protocol:

To de determined

In vivo protocol:

1: "Efficacy and safety of ralinepag, a novel oral IP agonist, in PAH patients on mono or dual background therapy: results from a phase 2 randomised, parallel group, placebo-controlled trial." F. Torres, H. Farber, A. Ristic, et al. Eur Respir J 2019; 54: 1901030. Eur Respir J. 2024 Apr 18;63(4):1951030. doi: 10.1183/13993003.51030-2019. Erratum for: Eur Respir J. 2019 Oct 10;54(4):1901030. doi: 10.1183/13993003.01030-2019. PMID: 38636973. 2: Barberà J, Jansa P, Klings E, Ristić A, Keogh A, Solum D, Rao Y, Grover R, Saib I, Sood N. Ralinepag Phase II Open-Label Extension Study in Patients with Pulmonary Arterial Hypertension. Adv Ther. 2024 Mar;41(3):1062-1074. doi: 10.1007/s12325-023-02769-7. Epub 2024 Jan 10. PMID: 38198043; PMCID: PMC10879237. 3: Grundy JS, King CD, Adams JW, Cabell CH. Safety, tolerability, and pharmacokinetics of the selective prostacyclin receptor agonist ralinepag in single and multiple dosing studies of an immediate-release oral formulation in healthy volunteers. Pulm Circ. 2020 May 14;10(2):2045894020922814. doi: 10.1177/2045894020922814. PMID: 32489643; PMCID: PMC7238799. 4: Torres F, Farber H, Ristic A, McLaughlin V, Adams J, Zhang J, Klassen P, Shanahan W, Grundy J, Hoffmann I, Cabell C, Escribano Subías P, Sood N, Keogh A, D'Souza G, Rubin L. Efficacy and safety of ralinepag, a novel oral IP agonist, in PAH patients on mono or dual background therapy: results from a phase 2 randomised, parallel group, placebo-controlled trial. Eur Respir J. 2019 Oct 10;54(4):1901030. doi: 10.1183/13993003.01030-2019. Erratum in: Eur Respir J. 2024 Apr 18;63(4):1951030. doi: 10.1183/13993003.51030-2019. PMID: 31391223. 5: Tran TA, Kramer B, Shin YJ, Vallar P, Boatman PD, Zou N, Sage CR, Gharbaoui T, Krishnan A, Pal B, Shakya SR, Garrido Montalban A, Adams JW, Ramirez J, Behan DP, Shifrina A, Blackburn A, Leakakos T, Shi Y, Morgan M, Sadeque A, Chen W, Unett DJ, Gaidarov I, Chen X, Chang S, Shu HH, Tung SF, Semple G. Discovery of 2 -(((1r,4r)-4-(((4-Chlorophenyl)(phenyl)carbamoyl)oxy)methyl)cyclohexyl)methoxy)a cetate (Ralinepag): An Orally Active Prostacyclin Receptor Agonist for the Treatment of Pulmonary Arterial Hypertension. J Med Chem. 2017 Feb 9;60(3):913-927. doi: 10.1021/acs.jmedchem.6b00871. Epub 2017 Jan 19. PMID: 28072531.