SB-222200 | CAS#174635-69-9 | NK-3 receptor antagonist

MedKoo Cat#: 526724 | Name: SB-222200

Featured

Description:

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

SB-222200 is a central nervous system penetrant, potent and selective NK-3 receptor antagonist.

Chemical Structure

SB-222200

CAS#174635-69-9

Theoretical Analysis

MedKoo Cat#: 526724

Name: SB-222200

CAS#: 174635-69-9

Chemical Formula: C26H24N2O

Exact Mass: 380.1889

Molecular Weight: 380.49

Elemental Analysis: C, 82.07; H, 6.36; N, 7.36; O, 4.20

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

SB-222200; SB222200; SB 222200.

IUPAC/Chemical Name

3-Methyl-2-phenyl-N-[(1S)-1-phenylpropyl]-4-quinolinecarboxamide

InChi Key

MQNYRKWJSMQECI-QFIPXVFZSA-N

InChi Code

InChI=1S/C26H24N2O/c1-3-22(19-12-6-4-7-13-19)28-26(29)24-18(2)25(20-14-8-5-9-15-20)27-23-17-11-10-16-21(23)24/h4-17,22H,3H2,1-2H3,(H,28,29)/t22-/m0/s1

SMILES Code

O=C(C1=C(C)C(C2=CC=CC=C2)=NC3=CC=CC=C13)N[C@H](C4=CC=CC=C4)CC

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

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:

SB-222200 inhibited (125)I-[MePhe(7)]neurokinin B (NKB) binding to Chinese hamster ovary (CHO) cell membranes stably expressing the hNK-3 receptor (CHO-hNK-3R) with a K(i) = 4.4 nM and antagonized NKB-induced Ca(2+) mobilization in HEK 293 cells stably expressing the hNK-3 receptor (HEK 293-hNK-3R) with an IC(50) = 18.4 nM. SB-222200 was selective for hNK-3 receptors compared with hNK-1 (K(i) > 100,000 nM) and hNK-2 receptors (K(i) = 250 nM).

In vitro activity:

SB-222200 has potential for alleviating NLRP3-dependent inflammatory diseases. In this study, SB-222200 effectively inhibited NLRP3 inflammasome activation in macrophages while not affecting other inflammasomes. It blocked the NEK7-NLRP3 interaction and NLRP3 oligomerization. Reference: Cell Mol Life Sci. 2023 Jul 27;80(8):230. https://pubmed.ncbi.nlm.nih.gov/37498355/

In vivo activity:

In a rat model of schizophrenia, SB-222200 microinjection prevented changes in the distribution of NK3R in dopaminergic dendrites. However, SB-222200 did not affect the trafficking of NK3R to the nucleus of these neurons. SB-222200 may have future potential in further schizophrenia studies. Reference: Neuroscience. 2013 Sep 5;247:12-24. https://pubmed.ncbi.nlm.nih.gov/23673279/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	26.28
	DMSO	10.0	26.28
	Ethanol	15.0	39.42

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 380.49 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. Zhou Y, Yang Z, Ou Y, Cai H, Liu Z, Lin G, Liang S, Hua L, Yan Y, Zhang X, Wu R, Qin A, Hu W, Sun P. Discovery of a selective NLRP3-targeting compound with therapeutic activity in MSU-induced peritonitis and DSS-induced acute intestinal inflammation. Cell Mol Life Sci. 2023 Jul 27;80(8):230. doi: 10.1007/s00018-023-04881-x. PMID: 37498355. 2. Sarau HM, Griswold DE, Bush B, Potts W, Sandhu P, Lundberg D, Foley JJ, Schmidt DB, Webb EF, Martin LD, Legos JJ, Whitmore RG, Barone FC, Medhurst AD, Luttmann MA, Giardina GA, Hay DW. Nonpeptide tachykinin receptor antagonists. II. Pharmacological and pharmacokinetic profile of SB-222200, a central nervous system penetrant, potent and selective NK-3 receptor antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):373-81. PMID: 10992004. 3. Li SY, Li XF, Hu MH, Shao B, Poston L, Lightman SL, O'Byrne KT. Neurokinin B receptor antagonism decreases luteinising hormone pulse frequency and amplitude and delays puberty onset in the female rat. J Neuroendocrinol. 2014 Aug;26(8):521-7. doi: 10.1111/jne.12167. PMID: 24863620. 4. Hether S, Misono K, Lessard A. The neurokinin-3 receptor (NK3R) antagonist SB222200 prevents the apomorphine-evoked surface but not nuclear NK3R redistribution in dopaminergic neurons of the rat ventral tegmental area. Neuroscience. 2013 Sep 5;247:12-24. doi: 10.1016/j.neuroscience.2013.05.006. Epub 2013 May 11. PMID: 23673279.

In vitro protocol:

In vivo protocol:

1. Li SY, Li XF, Hu MH, Shao B, Poston L, Lightman SL, O'Byrne KT. Neurokinin B receptor antagonism decreases luteinising hormone pulse frequency and amplitude and delays puberty onset in the female rat. J Neuroendocrinol. 2014 Aug;26(8):521-7. doi: 10.1111/jne.12167. PMID: 24863620. 2. Hether S, Misono K, Lessard A. The neurokinin-3 receptor (NK3R) antagonist SB222200 prevents the apomorphine-evoked surface but not nuclear NK3R redistribution in dopaminergic neurons of the rat ventral tegmental area. Neuroscience. 2013 Sep 5;247:12-24. doi: 10.1016/j.neuroscience.2013.05.006. Epub 2013 May 11. PMID: 23673279.

1: Ivanova D, Voliotis M, Tsaneva-Atanasova K, O'Byrne KT, Li XF. NK3R signalling in the posterodorsal medial amygdala is involved in stress-induced suppression of pulsatile LH secretion in female mice. J Neuroendocrinol. 2024 May;36(5):e13384. doi: 10.1111/jne.13384. Epub 2024 Mar 22. PMID: 38516965; PMCID: PMC11411622. 2: Zhou Y, Yang Z, Ou Y, Cai H, Liu Z, Lin G, Liang S, Hua L, Yan Y, Zhang X, Wu R, Qin A, Hu W, Sun P. Discovery of a selective NLRP3-targeting compound with therapeutic activity in MSU-induced peritonitis and DSS-induced acute intestinal inflammation. Cell Mol Life Sci. 2023 Jul 27;80(8):230. doi: 10.1007/s00018-023-04881-x. PMID: 37498355; PMCID: PMC11073129. 3: Atre I, Mizrahi N, Levavi-Sivan B. Characteristics of Neurokinin-3 Receptor and Its Binding Sites by Mutational Analysis. Biology (Basel). 2021 Sep 27;10(10):968. doi: 10.3390/biology10100968. PMID: 34681067; PMCID: PMC8533089. 4: Umer A, Ługowska-Umer H, Schönborn-Kellenberger O, Korolkiewicz PK, Sein- Anand Ł, Kuziemski K, Korolkiewicz RP. Tachykinin Antagonists Reverse Ischemia/Reperfusion Gastrointestinal Motility Impairment in Rats. J Surg Res. 2020 Nov;255:510-516. doi: 10.1016/j.jss.2020.05.092. Epub 2020 Jul 3. PMID: 32629333. 5: Obata K, Shimo T, Okui T, Matsumoto K, Takada H, Takabatake K, Kunisada Y, Ibaragi S, Yoshioka N, Kishimoto K, Nagatsuka H, Sasaki A. Role of Neurokinin 3 Receptor Signaling in Oral Squamous Cell Carcinoma. Anticancer Res. 2017 Nov;37(11):6119-6123. doi: 10.21873/anticanres.12060. PMID: 29061792. 6: Garcia JP, Guerriero KA, Keen KL, Kenealy BP, Seminara SB, Terasawa E. Kisspeptin and Neurokinin B Signaling Network Underlies the Pubertal Increase in GnRH Release in Female Rhesus Monkeys. Endocrinology. 2017 Oct 1;158(10):3269-3280. doi: 10.1210/en.2017-00500. PMID: 28977601; PMCID: PMC5659687. 7: Parchim NF, Wang W, Iriyama T, Ashimi OA, Siddiqui AH, Blackwell S, Sibai B, Kellems RE, Xia Y. Neurokinin 3 receptor and phosphocholine transferase: missing factors for pathogenesis of C-reactive protein in preeclampsia. Hypertension. 2015 Feb;65(2):430-9. doi: 10.1161/HYPERTENSIONAHA.114.04439. Epub 2014 Dec 1. PMID: 25452470; PMCID: PMC4736731. 8: García-Ortega J, Pinto FM, Fernández-Sánchez M, Prados N, Cejudo-Román A, Almeida TA, Hernández M, Romero M, Tena-Sempere M, Candenas L. Expression of neurokinin B/NK3 receptor and kisspeptin/KISS1 receptor in human granulosa cells. Hum Reprod. 2014 Dec;29(12):2736-46. doi: 10.1093/humrep/deu247. Epub 2014 Oct 14. PMID: 25316443. 9: Endo T, Yanagawa Y, Komatsu Y. Substance P Activates Ca2+-Permeable Nonselective Cation Channels through a Phosphatidylcholine-Specific Phospholipase C Signaling Pathway in nNOS-Expressing GABAergic Neurons in Visual Cortex. Cereb Cortex. 2016 Feb;26(2):669-682. doi: 10.1093/cercor/bhu233. Epub 2014 Oct 14. PMID: 25316339. 10: Porter KL, Hileman SM, Hardy SL, Nestor CC, Lehman MN, Goodman RL. Neurokinin-3 receptor activation in the retrochiasmatic area is essential for the full pre-ovulatory luteinising hormone surge in ewes. J Neuroendocrinol. 2014 Nov;26(11):776-84. doi: 10.1111/jne.12180. PMID: 25040132; PMCID: PMC4201879. 11: Li SY, Li XF, Hu MH, Shao B, Poston L, Lightman SL, O'Byrne KT. Neurokinin B receptor antagonism decreases luteinising hormone pulse frequency and amplitude and delays puberty onset in the female rat. J Neuroendocrinol. 2014 Aug;26(8):521-7. doi: 10.1111/jne.12167. PMID: 24863620. 12: Grachev P, Li XF, Hu MH, Li SY, Millar RP, Lightman SL, O'Byrne KT. Neurokinin B signaling in the female rat: a novel link between stress and reproduction. Endocrinology. 2014 Jul;155(7):2589-601. doi: 10.1210/en.2013-2038. Epub 2014 Apr 7. PMID: 24708241. 13: Sakamoto K, Wakabayashi Y, Yamamura T, Tanaka T, Takeuchi Y, Mori Y, Okamura H. A population of kisspeptin/neurokinin B neurons in the arcuate nucleus may be the central target of the male effect phenomenon in goats. PLoS One. 2013 Nov 18;8(11):e81017. doi: 10.1371/journal.pone.0081017. PMID: 24260530; PMCID: PMC3832416. 14: Lemieux GA, Keiser MJ, Sassano MF, Laggner C, Mayer F, Bainton RJ, Werb Z, Roth BL, Shoichet BK, Ashrafi K. In silico molecular comparisons of C. elegans and mammalian pharmacology identify distinct targets that regulate feeding. PLoS Biol. 2013 Nov;11(11):e1001712. doi: 10.1371/journal.pbio.1001712. Epub 2013 Nov 19. PMID: 24260022; PMCID: PMC3833878. 15: de Croft S, Boehm U, Herbison AE. Neurokinin B activates arcuate kisspeptin neurons through multiple tachykinin receptors in the male mouse. Endocrinology. 2013 Aug;154(8):2750-60. doi: 10.1210/en.2013-1231. Epub 2013 Jun 6. PMID: 23744641. 16: Hether S, Misono K, Lessard A. The neurokinin-3 receptor (NK3R) antagonist SB222200 prevents the apomorphine-evoked surface but not nuclear NK3R redistribution in dopaminergic neurons of the rat ventral tegmental area. Neuroscience. 2013 Sep 5;247:12-24. doi: 10.1016/j.neuroscience.2013.05.006. Epub 2013 May 11. PMID: 23673279. 17: Broiz AC, Bassi GS, De Souza Silva MA, Brandão ML. Effects of neurokinin-1 and 3-receptor antagonists on the defensive behavior induced by electrical stimulation of the dorsal periaqueductal gray. Neuroscience. 2012 Jan 10;201:134-45. doi: 10.1016/j.neuroscience.2011.11.031. Epub 2011 Nov 22. PMID: 22123168. 18: Nwaneshiudu CA, Unterwald EM. NK-3 receptor antagonism prevents behavioral sensitization to cocaine: a role of glycogen synthase kinase-3 in the nucleus accumbens. J Neurochem. 2010 Nov;115(3):635-42. doi: 10.1111/j.1471-4159.2010.06973.x. Epub 2010 Sep 28. PMID: 20807318; PMCID: PMC2970658. 19: De Brito Gariepy H, Couture R. Blockade of tachykinin NK3 receptor reverses hypertension through a dopaminergic mechanism in the ventral tegmental area of spontaneously hypertensive rats. Br J Pharmacol. 2010 Dec;161(8):1868-84. doi: 10.1111/j.1476-5381.2010.01008.x. PMID: 20804497; PMCID: PMC3010589. 20: Jayasena CN, Dhillo WS. Neurokinin B and kisspeptin: sexual partners or single agents? Endocrinology. 2010 Sep;151(9):4090-1. doi: 10.1210/en.2010-0696. PMID: 20736403.