SB 204741
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MedKoo CAT#: 532645

CAS#: 152239-46-8

Description: SB-204741 is an antagonist of the serotonin (5-HT) receptor subtype 5-HT2B. It inhibits 5-HT-induced contraction of isolated rat stomach fundus, a tissue that endogenously expresses high levels of 5-HT2B receptors (pA2 = 7.95). SB-204741 is selective for 5-HT2B receptors over 5-HT1A, 5-HT1D, 5-HT1E, 5-HT2A, 5-HT2C, 5-HT3, 5-HT4, dopamine D1-3, histamine H1, α1- and α2-adrenergic, and GABAA receptors (Kis = 1-100 µM). In vivo, SB-204741 (1 mg/kg per day) prevents the development of pulmonary arterial hypertension (PAH) and reduces vascular stiffness in a Bmpr2 mutant mouse model of hereditary PAH. It also reduces blood pressure in DOCA-salt hypertensive rats.

Chemical Structure

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SB 204741
CAS# 152239-46-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532645
Name: SB 204741
CAS#: 152239-46-8
Chemical Formula: C14H14N4OS
Exact Mass: 286.09
Molecular Weight: 286.350
Elemental Analysis: C, 58.72; H, 4.93; N, 19.57; O, 5.59; S, 11.20

Price and Availability

Size Price Availability Quantity
10mg USD 450 2 Weeks
50mg USD 1250 2 Weeks
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Synonym: SB 204741; SB204741; SB-204741;

IUPAC/Chemical Name: 1-(1-methylindol-5-yl)-3-(3-methyl-1,2-thiazol-5-yl)urea

InChi Key: USFUFHFQWXDVMH-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H14N4OS/c1-9-7-13(20-17-9)16-14(19)15-11-3-4-12-10(8-11)5-6-18(12)2/h3-8H,1-2H3,(H2,15,16,19)

SMILES Code: O=C(NC1=CC(C)=NS1)NC2=CC3=C(N(C)C=C3)C=C2

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: SB 204741 is a selective and high affinity 5-HT2B antagonist with a pKi value of 7.1.
In vitro activity: SB 204741 effectively counteracted the enhanced tension development in the umbilical artery of preeclamptic pregnancies, contributing to its potential role in regulating vascular responses. Reference: Eur J Pharmacol. 2009 Mar 1;605(1-3):129-37. https://pubmed.ncbi.nlm.nih.gov/19248248/
In vivo activity: SB 204741 has potential in mitigating myocardial damage through multifaceted mechanisms. In a rat model of isoproterenol-induced myocardial remodeling, SB 204741 improved hemodynamic and ventricular functions. There were reductions in the expression of proteins associated with inflammation, stress kinases, and apoptotic factors, along with an increase in proteins related to heat shock response, autophagy, and cell survival. Reference: Apoptosis. 2015 Apr;20(4):455-65. https://pubmed.ncbi.nlm.nih.gov/25544272/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 349.22

Preparing Stock Solutions

The following data is based on the product molecular weight 286.35 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. Seto SW, Lam HY, Lau WS, Au AL, Lam TY, Chim SS, Ngai SM, Chan SW, Leung TY, Yeung JH, Kong SK, Leung GP, Lee SM, Kwan YW. Role of monoamine oxidases in the exaggerated 5-hydroxytryptamine-induced tension development of human isolated preeclamptic umbilical artery. Eur J Pharmacol. 2009 Mar 1;605(1-3):129-37. doi: 10.1016/j.ejphar.2008.12.054. PMID: 19248248. 2. Bharti S, Rani N, Bhatia J, Arya DS. 5-HT2B receptor blockade attenuates β-adrenergic receptor-stimulated myocardial remodeling in rats via inhibiting apoptosis: role of MAPKs and HSPs. Apoptosis. 2015 Apr;20(4):455-65. doi: 10.1007/s10495-014-1083-z. PMID: 25544272. 3. Aira Z, Buesa I, García Del Caño G, Bilbao J, Doñate F, Zimmermann M, Azkue JJ. Transient, 5-HT2B receptor-mediated facilitation in neuropathic pain: Up-regulation of PKCγ and engagement of the NMDA receptor in dorsal horn neurons. Pain. 2013 Sep;154(9):1865-1877. doi: 10.1016/j.pain.2013.06.009. Epub 2013 Jun 12. PMID: 23769718.
In vitro protocol: 1. Seto SW, Lam HY, Lau WS, Au AL, Lam TY, Chim SS, Ngai SM, Chan SW, Leung TY, Yeung JH, Kong SK, Leung GP, Lee SM, Kwan YW. Role of monoamine oxidases in the exaggerated 5-hydroxytryptamine-induced tension development of human isolated preeclamptic umbilical artery. Eur J Pharmacol. 2009 Mar 1;605(1-3):129-37. doi: 10.1016/j.ejphar.2008.12.054. PMID: 19248248.
In vivo protocol: 1. Bharti S, Rani N, Bhatia J, Arya DS. 5-HT2B receptor blockade attenuates β-adrenergic receptor-stimulated myocardial remodeling in rats via inhibiting apoptosis: role of MAPKs and HSPs. Apoptosis. 2015 Apr;20(4):455-65. doi: 10.1007/s10495-014-1083-z. PMID: 25544272. 2. Aira Z, Buesa I, García Del Caño G, Bilbao J, Doñate F, Zimmermann M, Azkue JJ. Transient, 5-HT2B receptor-mediated facilitation in neuropathic pain: Up-regulation of PKCγ and engagement of the NMDA receptor in dorsal horn neurons. Pain. 2013 Sep;154(9):1865-1877. doi: 10.1016/j.pain.2013.06.009. Epub 2013 Jun 12. PMID: 23769718.

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1: Ozdemir E, Demirkazik A, Taskıran AS, Arslan G. Effects of 5-HT1 and 5-HT 2 Receptor Agonists on Electromagnetic Field-Induced Analgesia in Rats. Bioelectromagnetics. 2019 Jul;40(5):319-330. doi: 10.1002/bem.22196. Epub 2019 May 31. PMID: 31152464.

2: Gocht A, Distler JHW, Spriewald B, Ramsperger-Gleixner M, Weyand M, Ensminger SM, Heim C. Effects of different serotonin receptor subtype antagonists on the development of cardiac allograft vasculopathy in murine aortic allografts. Transpl Immunol. 2018 Aug;49:43-53. doi: 10.1016/j.trim.2018.04.002. Epub 2018 Apr 9. PMID: 29649585.

3: Salzer I, Gantumur E, Yousuf A, Boehm S. Control of sensory neuron excitability by serotonin involves 5HT2C receptors and Ca(2+)-activated chloride channels. Neuropharmacology. 2016 Nov;110(Pt A):277-286. doi: 10.1016/j.neuropharm.2016.08.006. Epub 2016 Aug 7. PMID: 27511837; PMCID: PMC6192515.

4: Bharti S, Rani N, Bhatia J, Arya DS. 5-HT2B receptor blockade attenuates β-adrenergic receptor-stimulated myocardial remodeling in rats via inhibiting apoptosis: role of MAPKs and HSPs. Apoptosis. 2015 Apr;20(4):455-65. doi: 10.1007/s10495-014-1083-z. PMID: 25544272.

5: Aira Z, Buesa I, García Del Caño G, Bilbao J, Doñate F, Zimmermann M, Azkue JJ. Transient, 5-HT2B receptor-mediated facilitation in neuropathic pain: Up- regulation of PKCγ and engagement of the NMDA receptor in dorsal horn neurons. Pain. 2013 Sep;154(9):1865-1877. doi: 10.1016/j.pain.2013.06.009. Epub 2013 Jun 12. PMID: 23769718.

6: Aira Z, Buesa I, Del Caño GG, Salgueiro M, Mendiable N, Mingo J, Aguilera L, Bilbao J, Azkue JJ. Selective impairment of spinal mu-opioid receptor mechanism by plasticity of serotonergic facilitation mediated by 5-HT2A and 5-HT2B receptors. Pain. 2012 Jul;153(7):1418-1425. doi: 10.1016/j.pain.2012.03.017. Epub 2012 Apr 19. PMID: 22520172.

7: Bharti S, Singh R, Chauhan SS, Hussain T, Al-Attas OS, Arya DS. Phosphorylation of Akt/GSK-3β/eNOS amplifies 5-HT2B receptor blockade mediated anti-hypertrophic effect in rats. FEBS Lett. 2012 Jan 20;586(2):180-5. doi: 10.1016/j.febslet.2011.12.015. Epub 2011 Dec 26. Erratum in: FEBS Lett. 2012 Jun 21;586(13):1832. PMID: 22210189.

8: Shahi PK, Choi S, Zuo DC, Yeum CH, Yoon PJ, Lee J, Kim YD, Park CG, Kim MY, Shin HR, Oh HJ, Jun JY. 5-hydroxytryptamine generates tonic inward currents on pacemaker activity of interstitial cells of cajal from mouse small intestine. Korean J Physiol Pharmacol. 2011 Jun;15(3):129-35. doi: 10.4196/kjpp.2011.15.3.129. Epub 2011 Jun 30. PMID: 21860590; PMCID: PMC3154376.

9: Futuro Neto HA, Macedo SM, Silva NF, Cabral AM, Pires JG. Central 5-HT(2A) receptors modulate the vagal bradycardia in response to activation of the von Bezold-Jarisch reflex in anesthetized rats. Braz J Med Biol Res. 2011 Mar;44(3):224-8. doi: 10.1590/s0100-879x2011007500016. Epub 2011 Feb 4. PMID: 21344136.

10: Rekik M, Lluel P, Palea S. 5-Hydroxytryptamine potentiates neurogenic contractions of rat isolated urinary bladder through both 5-HT(7) and 5-HT(2C) receptors. Eur J Pharmacol. 2011 Jan 10;650(1):403-10. doi: 10.1016/j.ejphar.2010.10.027. Epub 2010 Oct 20. PMID: 20969855.

11: Tubío RI, Pérez-Maceira J, Aldegunde M. Homeostasis of glucose in the rainbow trout (Oncorhynchus mykiss Walbaum): the role of serotonin. J Exp Biol. 2010 Jun 1;213(11):1813-21. doi: 10.1242/jeb.035444. PMID: 20472767.

12: Aira Z, Buesa I, Salgueiro M, Bilbao J, Aguilera L, Zimmermann M, Azkue JJ. Subtype-specific changes in 5-HT receptor-mediated modulation of C fibre-evoked spinal field potentials are triggered by peripheral nerve injury. Neuroscience. 2010 Jul 14;168(3):831-41. doi: 10.1016/j.neuroscience.2010.04.032. Epub 2010 Apr 20. PMID: 20412834.

13: Bai CF, Liu JC, Zhao R, Cao W, Liu SB, Zhang XN, Guo HJ, Yang Q, Yi DH, Zhao MG. Role of 5-HT 2B receptors in cardiomyocyte apoptosis in noradrenaline- induced cardiomyopathy in rats. Clin Exp Pharmacol Physiol. 2010 Jul;37(7):e145-51. doi: 10.1111/j.1440-1681.2010.05388.x. Epub 2010 Mar 30. PMID: 20374255.

14: Seto SW, Lam HY, Lau WS, Au AL, Lam TY, Chim SS, Ngai SM, Chan SW, Leung TY, Yeung JH, Kong SK, Leung GP, Lee SM, Kwan YW. Role of monoamine oxidases in the exaggerated 5-hydroxytryptamine-induced tension development of human isolated preeclamptic umbilical artery. Eur J Pharmacol. 2009 Mar 1;605(1-3):129-37. doi: 10.1016/j.ejphar.2008.12.054. PMID: 19248248.

15: Papageorgiou A, Denef C. Stimulation of growth hormone release by 5-hydroxytryptamine (5-HT) in cultured rat anterior pituitary cell aggregates: evidence for mediation by 5-HT2B, 5-HT7, 5-HT1B, and ketanserin-sensitive receptors. Endocrinology. 2007 Sep;148(9):4509-22. doi: 10.1210/en.2007-0034. Epub 2007 Jun 21. PMID: 17584957.

16: Filip M, Bubar MJ, Cunningham KA. Contribution of serotonin (5-HT) 5-HT2 receptor subtypes to the discriminative stimulus effects of cocaine in rats. Psychopharmacology (Berl). 2006 Jan;183(4):482-9. doi: 10.1007/s00213-005-0197-y. Epub 2005 Oct 28. PMID: 16261316.

17: Delesalle C, Deprez P, Schuurkes JA, Lefebvre RA. Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum. Br J Pharmacol. 2006 Jan;147(1):23-35. doi: 10.1038/sj.bjp.0706431. PMID: 16230998; PMCID: PMC1615837.

18: Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, Kihira K, Dohi T. Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities. Brain Res. 2005 Sep 28;1057(1-2):153-60. doi: 10.1016/j.brainres.2005.07.049. PMID: 16125150.

19: Holohean AM, Hackman JC. Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones. Br J Pharmacol. 2004 Oct;143(3):351-60. doi: 10.1038/sj.bjp.0705935. Epub 2004 Aug 31. PMID: 15339859; PMCID: PMC1575347.

20: Filip M, Bubar MJ, Cunningham KA. Contribution of serotonin (5-hydroxytryptamine; 5-HT) 5-HT2 receptor subtypes to the hyperlocomotor effects of cocaine: acute and chronic pharmacological analyses. J Pharmacol Exp Ther. 2004 Sep;310(3):1246-54. doi: 10.1124/jpet.104.068841. Epub 2004 May 6. PMID: 15131246.