SB-222200
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526724

CAS#: 174635-69-9

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


Chemical Structure

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SB-222200
CAS# 174635-69-9

Theoretical Analysis

MedKoo Cat#: 526724
Name: SB-222200
CAS#: 174635-69-9
Chemical Formula: C26H24N2O
Exact Mass: 380.19
Molecular Weight: 380.490
Elemental Analysis: C, 82.07; H, 6.36; N, 7.36; O, 4.20

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 2650 2 Weeks
1g USD 3850 2 Weeks
2g USD 6450 2 Weeks
Bulk inquiry

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:
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/

Solubility Data

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

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.

Recalculate based on batch purity %
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: 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.
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.

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1: Bennacef I, Perrio C, Lasne MC, Barré L. Functionalization through lithiation
of (S)-N-(1-phenylpropyl)-2-phenylquinoline-4-carboxamide. Application to the
labeling with carbon-11 of NK-3 receptor antagonist SB 222200. J Org Chem. 2007
Mar 16;72(6):2161-5. Epub 2007 Feb 24. PubMed PMID: 17319724.


2: King AG, Sanger GJ. Effect of a selective and potent central nervous system
penetrant, neurokinin-3 receptor antagonist (SB-222200), on cisplatin-induced
emesis in the ferret. Neurosci Lett. 2005 Mar 7;376(1):5-8. Epub 2004 Dec 2.
PubMed PMID: 15694264.


3: 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. PubMed PMID: 10992004.