Olorinab | CAS#1268881-20-4 | CB2 agonist

MedKoo Cat#: 584932 | Name: Olorinab

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Description:

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

Olorinab is a highly potent and selective CB2 agonist for the treatment of chronic pain. Olorinab reduces nociceptor hypersensitivity in colitis and CVH states in a concentration- and CB2-dependent manner.

Chemical Structure

Olorinab

CAS#1268881-20-4

Theoretical Analysis

MedKoo Cat#: 584932

Name: Olorinab

CAS#: 1268881-20-4

Chemical Formula: C18H23N5O3

Exact Mass: 357.1801

Molecular Weight: 357.41

Elemental Analysis: C, 60.49; H, 6.49; N, 19.59; O, 13.43

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 245.00	2 Weeks
5mg	USD 490.00	2 Weeks

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Related CAS #

No Data

Synonym

Olorinab; APD371; APD 371; APD-371

IUPAC/Chemical Name

1H-Cyclopropa(4,5)cyclopenta(1,2-c)pyrazole-3-carboxamide, 4,4a,5,5a-tetrahydro-N-((1S)-1-(hydroxymethyl)-2,2-dimethylpropyl)-1-(4-oxido-2-pyrazinyl)-, (4aS,5aS)-

InChi Key

ACSQLTBPYZSGBA-GMXVVIOVSA-N

InChi Code

InChI=1S/C18H23N5O3/c1-18(2,3)13(9-24)20-17(25)15-12-7-10-6-11(10)16(12)23(21-15)14-8-22(26)5-4-19-14/h4-5,8,10-11,13,24H,6-7,9H2,1-3H3,(H,20,25)/t10-,11-,13+/m0/s1

SMILES Code

O=C(C1=NN(C2=C[N+]([O-])=CC=N2)C3=C1C[C@@]4([H])[C@]3([H])C4)N[C@H](CO)C(C)(C)C

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olorinab (APD 371) is a highly potent, selective and fully efficacious cannabinoid receptor type 2 (CB2) agonist, with an EC50 of 6.2 nM for hCB2.

In vitro activity:

TBD

In vivo activity:

The discovery of a novel, selective and fully efficacious CB2 agonist with satisfactory pharmacokinetic and pharmaceutical properties is described. Compound 6 (APD371) was efficacious in a rat model of osteoarthritis pain following oral administration and, in contrast to morphine, maintained its analgesic effect throughout a 5-day subchronic treatment paradigm. These data were consistent with this study’s hypothesis that full agonist efficacy is required for efficient internalization and recycling of the CB2 receptor to avoid tachyphylaxis. Reference: ACS Med Chem Lett. 2017 Nov 30;8(12):1309-1313. https://pubmed.ncbi.nlm.nih.gov/29259753/

	Solvent	mg/mL	mM
Solubility
	DMSO	200.0	559.58

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 357.41 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. Castro J, Garcia-Caraballo S, Maddern J, Schober G, Lumsden A, Harrington A, Schmiel S, Lindstrom B, Adams J, Brierley SM. Olorinab (APD371), a peripherally acting, highly selective, full agonist of the cannabinoid receptor 2, reduces colitis-induced acute and chronic visceral hypersensitivity in rodents. Pain. 2022 Jan 1;163(1):e72-e86. doi: 10.1097/j.pain.0000000000002314. PMID: 33863856; PMCID: PMC8675055. 2. Han S, Thoresen L, Jung JK, Zhu X, Thatte J, Solomon M, Gaidarov I, Unett DJ, Yoon WH, Barden J, Sadeque A, Usmani A, Chen C, Semple G, Grottick AJ, Al-Shamma H, Christopher R, Jones RM. Discovery of APD371: Identification of a Highly Potent and Selective CB2 Agonist for the Treatment of Chronic Pain. ACS Med Chem Lett. 2017 Nov 30;8(12):1309-1313. doi: 10.1021/acsmedchemlett.7b00396. PMID: 29259753; PMCID: PMC5733264.

In vitro protocol:

TBD

In vivo protocol:

1: Mozaffari S, Nikfar S, Abdollahi M. Drugs of the future for diarrhea- predominant irritable bowel syndrome: an overview of current investigational drugs. Expert Opin Investig Drugs. 2024 Mar;33(3):219-228. doi: 10.1080/13543784.2024.2320703. Epub 2024 Feb 23. PMID: 38366822. 2: Camilleri M, Zheng T. Cannabinoids and the Gastrointestinal Tract. Clin Gastroenterol Hepatol. 2023 Dec;21(13):3217-3229. doi: 10.1016/j.cgh.2023.07.031. Epub 2023 Sep 9. PMID: 37678488; PMCID: PMC10872845. 3: Chang L, Cash BD, Lembo A, Kunkel DC, English BA, Lindstrom B, Gu G, Skare S, Gilder K, Turner S, Cataldi F, Lipkis D, Tack J. Efficacy and safety of olorinab, a full agonist of the cannabinoid receptor 2, for the treatment of abdominal pain in patients with irritable bowel syndrome: Results from a phase 2b randomized placebo-controlled trial (CAPTIVATE). Neurogastroenterol Motil. 2023 May;35(5):e14539. doi: 10.1111/nmo.14539. Epub 2023 Feb 5. PMID: 36740814. 4: Sinopoulou V, Gordon M, Akobeng AK, Gasparetto M, Sammaan M, Vasiliou J, Dovey TM. Interventions for the management of abdominal pain in Crohn's disease and inflammatory bowel disease. Cochrane Database Syst Rev. 2021 Nov 29;11(11):CD013531. doi: 10.1002/14651858.CD013531.pub2. PMID: 34844288; PMCID: PMC8629648. 5: Castro J, Garcia-Caraballo S, Maddern J, Schober G, Lumsden A, Harrington A, Schmiel S, Lindstrom B, Adams J, Brierley SM. Olorinab (APD371), a peripherally acting, highly selective, full agonist of the cannabinoid receptor 2, reduces colitis-induced acute and chronic visceral hypersensitivity in rodents. Pain. 2022 Jan 1;163(1):e72-e86. doi: 10.1097/j.pain.0000000000002314. PMID: 33863856; PMCID: PMC8675055. 6: Yacyshyn BR, Hanauer S, Klassen P, English BA, Stauber K, Barish CF, Gilder K, Turner S, Higgins PDR. Safety, Pharmacokinetics, and Efficacy of Olorinab, a Peripherally Acting, Highly Selective, Full Agonist of the Cannabinoid Receptor 2, in a Phase 2a Study of Patients With Chronic Abdominal Pain Associated With Crohn's Disease. Crohns Colitis 360. 2020 Oct 24;3(1):otaa089. doi: 10.1093/crocol/otaa089. PMID: 36777064; PMCID: PMC9802051. 7: Maselli DB, Camilleri M. Pharmacology, Clinical Effects, and Therapeutic Potential of Cannabinoids for Gastrointestinal and Liver Diseases. Clin Gastroenterol Hepatol. 2021 Sep;19(9):1748-1758.e2. doi: 10.1016/j.cgh.2020.04.020. Epub 2020 Jul 13. PMID: 32673642; PMCID: PMC7854774.