SB-334867 free base
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MedKoo CAT#: 530968

CAS#: 792173-99-0 (free base)

Description: SB-334867 is an orexin antagonist. It was the first non-peptide antagonist developed that is selective for the orexin receptor subtype OX1, with around 50x selectivity for OX1 over OX2 receptors. It has been shown to produce sedative and anorectic effects in animals, and has been useful in characterising the orexinergic regulation of brain systems involved with appetite and sleep, as well as other physiological processes. Orexin antagonists have multiple potential clinical applications including the treatment of drug addiction, insomnia, obesity and diabetes.

Chemical Structure

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SB-334867 free base
CAS# 792173-99-0 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530968
Name: SB-334867 free base
CAS#: 792173-99-0 (free base)
Chemical Formula: C17H13N5O2
Exact Mass: 319.11
Molecular Weight: 319.324
Elemental Analysis: C, 63.94; H, 4.10; N, 21.93; O, 10.02

Price and Availability

Size Price Availability Quantity
10mg USD 110 Ready to Ship
25mg USD 190 Ready to ship
50mg USD 350 Ready to ship
100mg USD 550 Ready to ship
200mg USD 950 Ready to ship
500mg USD 1950 Ready to ship
1g USD 3250 Ready to ship
2g USD 5850 Ready to ship
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Related CAS #: 792173-99-0 (free base)   249889-64-3 (HCl)    

Synonym: SB-334867; SB 334867; SB334867.

IUPAC/Chemical Name: N-(2-methyl-6-benzoxazolyl)-N'-1,5-naphthyridin-4-yl-urea

InChi Key: AKMNUCBQGHFICM-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H13N5O2/c1-10-20-12-5-4-11(9-15(12)24-10)21-17(23)22-14-6-8-18-13-3-2-7-19-16(13)14/h2-9H,1H3,(H2,18,21,22,23)

SMILES Code: O=C(NC1=CC=NC2=CC=CN=C12)NC3=CC=C4N=C(C)OC4=C3

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: >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:

Biological target: SB-334867 free base is an OX1 receptor antagonist that shows selectivity over OX2 (pKb=7.4), 100-fold over 5-HT2B, 5-HT2C with pKi values of 5.4 and 5.3, respectively. SB-334867 reduces ethanol consumption and inhibits the acquisition of morphine-induced sensitization to locomotor activity in vivo.
In vitro activity: SB-334867 acts as a non-peptide antagonist specific to the OX1 receptor. SB-334867 inhibited orexin-A and orexin-B-induced calcium responses, but had no effect on the UTP-induced calcium response in CHO-OX1 cells. SB-334867 also inhibited OX2 mediated calcium responses. SB-334867 was devoid of agonist properties in either cell-line. Reference: Br J Pharmacol. 2001 Mar;132(6):1179-82. https://pubmed.ncbi.nlm.nih.gov/11250867/
In vivo activity: SB-334867 inhibited the acquisition of morphine-induced sensitization to locomotor activity in mice. SB-334867 treatment caused significant alterations in the mRNA expression of orexin, dopamine, and adenosine receptors in multiple brain structures. Additionally, there were changes in the expression of markers associated with glial cells (GFAP and Iba-1). Reference: Mol Neurobiol. 2018 Nov;55(11):8473-8485. https://pubmed.ncbi.nlm.nih.gov/29557083/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 48.3 151.29
0.1M HCl 6.0 18.79
Ethanol 4.1 12.84

Preparing Stock Solutions

The following data is based on the product molecular weight 319.32 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. Wen J, Zhao Y, Shen Y, Guo L. Effect of orexin A on apoptosis in BGC-823 gastric cancer cells via OX1R through the AKT signaling pathway. Mol Med Rep. 2015 May;11(5):3439-44. doi: 10.3892/mmr.2015.3190. Epub 2015 Jan 13. PMID: 25586545. 2. Smart D, Sabido-David C, Brough SJ, Jewitt F, Johns A, Porter RA, Jerman JC. SB-334867-A: the first selective orexin-1 receptor antagonist. Br J Pharmacol. 2001 Mar;132(6):1179-82. doi: 10.1038/sj.bjp.0703953. PMID: 11250867; PMCID: PMC1572677. 3. Stanquini LA, Sartim AG, Joca SRL. Orexin A injection into the ventral medial prefrontal cortex induces antidepressant-like effects: Possible involvement of local Orexin-1 and Trk receptors. Behav Brain Res. 2020 Oct 1;395:112866. doi: 10.1016/j.bbr.2020.112866. Epub 2020 Aug 19. PMID: 32827568. 4. Łupina M, Tarnowski M, Baranowska-Bosiacka I, Talarek S, Listos P, Kotlińska J, Gutowska I, Listos J. SB-334867 (an Orexin-1 Receptor Antagonist) Effects on Morphine-Induced Sensitization in Mice-a View on Receptor Mechanisms. Mol Neurobiol. 2018 Nov;55(11):8473-8485. doi: 10.1007/s12035-018-0993-0. Epub 2018 Mar 20. PMID: 29557083; PMCID: PMC6153720.
In vitro protocol: 1. Wen J, Zhao Y, Shen Y, Guo L. Effect of orexin A on apoptosis in BGC-823 gastric cancer cells via OX1R through the AKT signaling pathway. Mol Med Rep. 2015 May;11(5):3439-44. doi: 10.3892/mmr.2015.3190. Epub 2015 Jan 13. PMID: 25586545. 2. Smart D, Sabido-David C, Brough SJ, Jewitt F, Johns A, Porter RA, Jerman JC. SB-334867-A: the first selective orexin-1 receptor antagonist. Br J Pharmacol. 2001 Mar;132(6):1179-82. doi: 10.1038/sj.bjp.0703953. PMID: 11250867; PMCID: PMC1572677.
In vivo protocol: 1. Stanquini LA, Sartim AG, Joca SRL. Orexin A injection into the ventral medial prefrontal cortex induces antidepressant-like effects: Possible involvement of local Orexin-1 and Trk receptors. Behav Brain Res. 2020 Oct 1;395:112866. doi: 10.1016/j.bbr.2020.112866. Epub 2020 Aug 19. PMID: 32827568. 2. Łupina M, Tarnowski M, Baranowska-Bosiacka I, Talarek S, Listos P, Kotlińska J, Gutowska I, Listos J. SB-334867 (an Orexin-1 Receptor Antagonist) Effects on Morphine-Induced Sensitization in Mice-a View on Receptor Mechanisms. Mol Neurobiol. 2018 Nov;55(11):8473-8485. doi: 10.1007/s12035-018-0993-0. Epub 2018 Mar 20. PMID: 29557083; PMCID: PMC6153720.

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1: Hooshmand B, Azizi H, Javan M, Semnanian S. Intra-LC microinjection of orexin type-1 receptor antagonist SB-334867 attenuates the expression of glutamate-induced opiate withdrawal like signs during the active phase in rats. Neurosci Lett. 2017 Jan 1;636:276-281. doi: 10.1016/j.neulet.2016.10.051. Epub 2016 Nov 2. PubMed PMID: 27816550.

2: Kordi Jaz E, Moghimi A, Fereidoni M, Asadi S, Shamsizadeh A, Roohbakhsh A. SB-334867, an orexin receptor 1 antagonist, decreased seizure and anxiety in pentylenetetrazol-kindled rats. Fundam Clin Pharmacol. 2017 Apr;31(2):201-207. doi: 10.1111/fcp.12249. Epub 2016 Nov 23. PubMed PMID: 27739093.

3: Mayannavar S, Rashmi KS, Rao YD, Yadav S, Ganaraja B. Effect of Orexin A antagonist (SB-334867) infusion into the nucleus accumbens on consummatory behavior and alcohol preference in Wistar rats. Indian J Pharmacol. 2016 Jan-Feb;48(1):53-8. doi: 10.4103/0253-7613.174528. PubMed PMID: 26997723; PubMed Central PMCID: PMC4778208.

4: Socała K, Szuster-Ciesielska A, Wlaź P. SB 334867, a selective orexin receptor type 1 antagonist, elevates seizure threshold in mice. Life Sci. 2016 Apr 1;150:81-8. doi: 10.1016/j.lfs.2016.02.075. Epub 2016 Feb 23. PubMed PMID: 26916826.

5: Vanderhaven MW, Cornish JL, Staples LG. The orexin-1 receptor antagonist SB-334867 decreases anxiety-like behavior and c-Fos expression in the hypothalamus of rats exposed to cat odor. Behav Brain Res. 2015 Feb 1;278:563-8. doi: 10.1016/j.bbr.2014.10.028. Epub 2014 Oct 30. PubMed PMID: 25447305.

6: Staples LG, Cornish JL. The orexin-1 receptor antagonist SB-334867 attenuates anxiety in rats exposed to cat odor but not the elevated plus maze: an investigation of Trial 1 and Trial 2 effects. Horm Behav. 2014 Mar;65(3):294-300. doi: 10.1016/j.yhbeh.2013.12.014. Epub 2014 Jan 4. PubMed PMID: 24397997.

7: Azhdari-Zarmehri H, Esmaeili MH, Sofiabadi M, Haghdoost-Yazdi H. Orexin receptor type-1 antagonist SB-334867 decreases morphine-induced antinociceptive effect in formalin test. Pharmacol Biochem Behav. 2013 Nov;112:64-70. doi: 10.1016/j.pbb.2013.09.018. Epub 2013 Oct 12. PubMed PMID: 24125787.

8: McElhinny CJ Jr, Lewin AH, Mascarella SW, Runyon S, Brieaddy L, Carroll FI. Hydrolytic instability of the important orexin 1 receptor antagonist SB-334867: possible confounding effects on in vivo and in vitro studies. Bioorg Med Chem Lett. 2012 Nov 1;22(21):6661-4. doi: 10.1016/j.bmcl.2012.08.109. Epub 2012 Sep 7. PubMed PMID: 23031594.

9: Ranjbar-Slamloo Y, Azizi H, Fathollahi Y, Semnanian S. Orexin receptor type-1 antagonist SB-334867 inhibits the development of morphine analgesic tolerance in rats. Peptides. 2012 May;35(1):56-9. doi: 10.1016/j.peptides.2012.02.023. Epub 2012 Mar 6. PubMed PMID: 22421510.

10: Rusyniak DE, Zaretsky DV, Zaretskaia MV, Durant PJ, DiMicco JA. The orexin-1 receptor antagonist SB-334867 decreases sympathetic responses to a moderate dose of methamphetamine and stress. Physiol Behav. 2012 Dec 5;107(5):743-50. doi: 10.1016/j.physbeh.2012.02.010. Epub 2012 Feb 14. PubMed PMID: 22361264; PubMed Central PMCID: PMC3371311.

11: Putula J, Kukkonen JP. Mapping of the binding sites for the OX1 orexin receptor antagonist, SB-334867, using orexin/hypocretin receptor chimaeras. Neurosci Lett. 2012 Jan 6;506(1):111-5. doi: 10.1016/j.neulet.2011.10.061. Epub 2011 Nov 2. PubMed PMID: 22079339.

12: Perrey DA, Gilmour BP, Runyon SP, Thomas BF, Zhang Y. Diaryl urea analogues of SB-334867 as orexin-1 receptor antagonists. Bioorg Med Chem Lett. 2011 May 15;21(10):2980-5. doi: 10.1016/j.bmcl.2011.03.048. Epub 2011 Mar 21. PubMed PMID: 21478014; PubMed Central PMCID: PMC3085582.

13: Jupp B, Krivdic B, Krstew E, Lawrence AJ. The orexin₁ receptor antagonist SB-334867 dissociates the motivational properties of alcohol and sucrose in rats. Brain Res. 2011 May 19;1391:54-9. doi: 10.1016/j.brainres.2011.03.045. Epub 2011 Mar 23. PubMed PMID: 21439948.

14: Mediavilla C, Cabello V, Risco S. SB-334867-A, a selective orexin-1 receptor antagonist, enhances taste aversion learning and blocks taste preference learning in rats. Pharmacol Biochem Behav. 2011 May;98(3):385-91. doi: 10.1016/j.pbb.2011.01.021. Epub 2011 Feb 2. PubMed PMID: 21295056.

15: Hutcheson DM, Quarta D, Halbout B, Rigal A, Valerio E, Heidbreder C. Orexin-1 receptor antagonist SB-334867 reduces the acquisition and expression of cocaine-conditioned reinforcement and the expression of amphetamine-conditioned reward. Behav Pharmacol. 2011 Apr;22(2):173-81. doi: 10.1097/FBP.0b013e328343d761. PubMed PMID: 21285875.

16: Dhaher R, Hauser SR, Getachew B, Bell RL, McBride WJ, McKinzie DL, Rodd ZA. The Orexin-1 Receptor Antagonist SB-334867 Reduces Alcohol Relapse Drinking, but not Alcohol-Seeking, in Alcohol-Preferring (P) Rats. J Addict Med. 2010 Sep;4(3):153-9. doi: 10.1097/ADM.0b013e3181bd893f. PubMed PMID: 20871792; PubMed Central PMCID: PMC2943642.

17: Quarta D, Valerio E, Hutcheson DM, Hedou G, Heidbreder C. The orexin-1 receptor antagonist SB-334867 reduces amphetamine-evoked dopamine outflow in the shell of the nucleus accumbens and decreases the expression of amphetamine sensitization. Neurochem Int. 2010 Jan;56(1):11-5. doi: 10.1016/j.neuint.2009.08.012. Epub 2009 Sep 6. PubMed PMID: 19737591.

18: Boschen KE, Fadel JR, Burk JA. Systemic and intrabasalis administration of the orexin-1 receptor antagonist, SB-334867, disrupts attentional performance in rats. Psychopharmacology (Berl). 2009 Oct;206(2):205-13. doi: 10.1007/s00213-009-1596-2. Epub 2009 Jul 3. PubMed PMID: 19575184.

19: Jochem J. Orexin type 1 receptor antagonist SB 334867 inhibits the central histamine-induced resuscitating effect in rats subjected to haemorrhagic shock. Inflamm Res. 2009 Apr;58 Suppl 1:36-7. doi: 10.1007/s00011-009-0657-7. PubMed PMID: 19271123.

20: Nair SG, Golden SA, Shaham Y. Differential effects of the hypocretin 1 receptor antagonist SB 334867 on high-fat food self-administration and reinstatement of food seeking in rats. Br J Pharmacol. 2008 May;154(2):406-16. doi: 10.1038/bjp.2008.3. Epub 2008 Jan 28. PubMed PMID: 18223663; PubMed Central PMCID: PMC2442445.