BIBO-3304 TFA | CAS#191868-14-1 | Y1 receptor antagonist

MedKoo Cat#: 584202 | Name: BIBO-3304 TFA

Description:

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

BIBO-3304 is a selective Y1 receptor antagonist. Y1 receptor proteins from neuropeptide Y have a roll in appetite stimulation.

Chemical Structure

BIBO-3304 TFA

CAS#191868-14-1 (TFA)

Theoretical Analysis

MedKoo Cat#: 584202

Name: BIBO-3304 TFA

CAS#: 191868-14-1 (TFA)

Chemical Formula: C33H37F6N7O7

Exact Mass: 0.0000

Molecular Weight: 757.69

Elemental Analysis: C, 52.31; H, 4.92; F, 15.04; N, 12.94; O, 14.78

Price and Availability

Size	Price	Availability
50mg	USD 1,250.00	2 Weeks
100mg	USD 1,950.00	2 Weeks
200mg	USD 2,950.00	2 Weeks
500mg	USD 3,950.00	2 Weeks
1g	USD 6,450.00	2 Weeks
2g	USD 9,650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

191868-13-0 (free base) 191868-14-1 (TFA)

Synonym

BIBO-3304; BIBO 3304; BIBO3304; BIBO-3304 TFA

IUPAC/Chemical Name

(R)-2-(2,2-diphenylacetamido)-5-guanidino-N-(4-(ureidomethyl)benzyl)pentanamide bis(2,2,2-trifluoroacetate)

InChi Key

XWZMETGYCRXJJH-PPLJNSMQSA-N

InChi Code

InChI=1S/C29H35N7O3.2C2HF3O2/c30-28(31)33-17-7-12-24(26(37)34-18-20-13-15-21(16-14-20)19-35-29(32)39)36-27(38)25(22-8-3-1-4-9-22)23-10-5-2-6-11-23;2*3-2(4,5)1(6)7/h1-6,8-11,13-16,24-25H,7,12,17-19H2,(H,34,37)(H,36,38)(H4,30,31,33)(H3,32,35,39);2*(H,6,7)/t24-;;/m1../s1

SMILES Code

O=C(N[C@@H](C(NCC1=CC=C(CNC(N)=O)C=C1)=O)CCCNC(N)=N)C(C2=CC=CC=C2)C3=CC=CC=C3.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

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:

BIBO3304 TFA is a neuropeptide Y (NPY) Y1 receptor antagonist, with subnanomolar affinity for both the human and the rat Y1 receptor with IC50s of 0.38 and 0.72 nM, respectively.

In vitro activity:

The selective Y1 receptor antagonist, BIBO 3304, concentration-dependently inhibited vasoconstrictive and proliferative effects of neuropeptide Y (NPY) in vitro. Reference: Br J Pharmacol. 2014 Aug;171(16):3895-907. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4128051/

In vivo activity:

Treatment with BIBO-3304, a NPY receptor antagonist, significantly suppressed development of house dust mite (HDM) induced airway hyperresponsiveness (AHR) and inflammation in wild-type mice.4 Reference: Am J Physiol Lung Cell Mol Physiol. 2019 Mar 1;316(3):L407-L417. https://journals.physiology.org/doi/full/10.1152/ajplung.00386.2018?rfr_dat=cr_pub++0pubmed&url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org

	Solvent	mg/mL	mM
Solubility
	DMSO	87.9	116.00
	Ethanol	15.2	19.99

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 757.69 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. Crnkovic S, Egemnazarov B, Jain P, Seay U, Gattinger N, Marsh LM, Bálint Z, Kovacs G, Ghanim B, Klepetko W, Schermuly RT, Weissmann N, Olschewski A, Kwapiszewska G. NPY/Y₁ receptor-mediated vasoconstrictory and proliferative effects in pulmonary hypertension. Br J Pharmacol. 2014 Aug;171(16):3895-907. doi: 10.1111/bph.12751. PMID: 24779394; PMCID: PMC4128051. 2. Oda N, Miyahara N, Taniguchi A, Morichika D, Senoo S, Fujii U, Itano J, Gion Y, Kiura K, Kanehiro A, Maeda Y. Requirement for neuropeptide Y in the development of type 2 responses and allergen-induced airway hyperresponsiveness and inflammation. Am J Physiol Lung Cell Mol Physiol. 2019 Mar 1;316(3):L407-L417. doi: 10.1152/ajplung.00386.2018. Epub 2019 Jan 3. PMID: 30604629.

In vitro protocol:

In vivo protocol:

1. Oda N, Miyahara N, Taniguchi A, Morichika D, Senoo S, Fujii U, Itano J, Gion Y, Kiura K, Kanehiro A, Maeda Y. Requirement for neuropeptide Y in the development of type 2 responses and allergen-induced airway hyperresponsiveness and inflammation. Am J Physiol Lung Cell Mol Physiol. 2019 Mar 1;316(3):L407-L417. doi: 10.1152/ajplung.00386.2018. Epub 2019 Jan 3. PMID: 30604629.

1: Shi Z, Li B, Brooks VL. Role of the Paraventricular Nucleus of the Hypothalamus in the Sympathoexcitatory Effects of Leptin. Hypertension. 2015 Nov;66(5):1034-41. doi: 10.1161/HYPERTENSIONAHA.115.06017. Epub 2015 Sep 14. PubMed PMID: 26370892; PubMed Central PMCID: PMC4798233. 2: Wierońska JM, Smiałowska M, Brański P, Gasparini F, Kłodzińska A, Szewczyk B, Pałucha A, Chojnacka-Wójcik E, Pilc A. In the amygdala anxiolytic action of mGlu5 receptors antagonist MPEP involves neuropeptide Y but not GABAA signaling. Neuropsychopharmacology. 2004 Mar;29(3):514-21. PubMed PMID: 14666119. 3: Crnkovic S, Egemnazarov B, Jain P, Seay U, Gattinger N, Marsh LM, Bálint Z, Kovacs G, Ghanim B, Klepetko W, Schermuly RT, Weissmann N, Olschewski A, Kwapiszewska G. NPY/Y₁ receptor-mediated vasoconstrictory and proliferative effects in pulmonary hypertension. Br J Pharmacol. 2014 Aug;171(16):3895-907. doi: 10.1111/bph.12751. PubMed PMID: 24779394; PubMed Central PMCID: PMC4128051. 4: Wierońska JM, Stachowicz K, Kłodzińska A, Smiałowska M, Pilc A. Intraamygdaloid administration of BIBO 3304 increases water intake and extends anxiolytic effects. Pol J Pharmacol. 2004 Nov-Dec;56(6):867-70. PubMed PMID: 15662103. 5: Maric T, Sedki F, Chafetz D, Schoela N, Shalev U. A role for neuropeptide Y Y5 but not the Y1-receptor subtype in food deprivation-induced reinstatement of heroin seeking in the rat. Psychopharmacology (Berl). 2011 Dec;218(4):693-701. doi: 10.1007/s00213-011-2362-9. Epub 2011 Jun 1. PubMed PMID: 21629996. 6: Cohen S, Vainer E, Matar MA, Kozlovsky N, Kaplan Z, Zohar J, Mathé AA, Cohen H. Diurnal fluctuations in HPA and neuropeptide Y-ergic systems underlie differences in vulnerability to traumatic stress responses at different zeitgeber times. Neuropsychopharmacology. 2015 Feb;40(3):774-90. doi: 10.1038/npp.2014.257. Epub 2014 Sep 22. PubMed PMID: 25241802; PubMed Central PMCID: PMC4289967. 7: Keller M, Schindler L, Bernhardt G, Buschauer A. Toward Labeled Argininamide-Type NPY Y1 Receptor Antagonists: Identification of a Favorable Propionylation Site in BIBO3304. Arch Pharm (Weinheim). 2015 Jun;348(6):390-8. doi: 10.1002/ardp.201400427. Epub 2015 Apr 17. PubMed PMID: 25884646. 8: Forbes S, Herzog H, Cox HM. A role for neuropeptide Y in the gender-specific gastrointestinal, corticosterone and feeding responses to stress. Br J Pharmacol. 2012 Aug;166(8):2307-16. doi: 10.1111/j.1476-5381.2012.01939.x. PubMed PMID: 22404240; PubMed Central PMCID: PMC3448895. 9: Keller M, Kaske M, Holzammer T, Bernhardt G, Buschauer A. Dimeric argininamide-type neuropeptide Y receptor antagonists: chiral discrimination between Y1 and Y4 receptors. Bioorg Med Chem. 2013 Nov 1;21(21):6303-22. doi: 10.1016/j.bmc.2013.08.065. Epub 2013 Sep 8. PubMed PMID: 24074877. 10: Morales-Medina JC, Dumont Y, Benoit CE, Bastianetto S, Flores G, Fournier A, Quirion R. Role of neuropeptide Y Y₁ and Y₂ receptors on behavioral despair in a rat model of depression with co-morbid anxiety. Neuropharmacology. 2012 Jan;62(1):200-8. doi: 10.1016/j.neuropharm.2011.06.030. Epub 2011 Jul 23. PubMed PMID: 21803058. 11: Abdel-Samad D, Perreault C, Ahmarani L, Avedanian L, Bkaily G, Magder S, D'Orléans-Juste P, Jacques D. Differences in neuropeptide Y-induced secretion of endothelin-1 in left and right human endocardial endothelial cells. Neuropeptides. 2012 Dec;46(6):373-82. doi: 10.1016/j.npep.2012.09.003. Epub 2012 Oct 26. PubMed PMID: 23107364. 12: Cohen H, Liu T, Kozlovsky N, Kaplan Z, Zohar J, Mathé AA. The neuropeptide Y (NPY)-ergic system is associated with behavioral resilience to stress exposure in an animal model of post-traumatic stress disorder. Neuropsychopharmacology. 2012 Jan;37(2):350-63. doi: 10.1038/npp.2011.230. Epub 2011 Oct 5. PubMed PMID: 21976046; PubMed Central PMCID: PMC3242318. 13: Sapunar D, Vukojević K, Kostić S, Puljak L. Attenuation of pain-related behavior evoked by injury through blockade of neuropeptide Y Y2 receptor. Pain. 2011 May;152(5):1173-81. doi: 10.1016/j.pain.2011.01.045. Epub 2011 Mar 3. PubMed PMID: 21376464. 14: Capurro D, Huidobro-Toro JP. The involvement of neuropeptide Y Y1 receptors in the blood pressure baroreflex: studies with BIBP 3226 and BIBO 3304. Eur J Pharmacol. 1999 Jul 9;376(3):251-5. PubMed PMID: 10448884. 15: Fendt M, Bürki H, Imobersteg S, Lingenhöhl K, McAllister KH, Orain D, Uzunov DP, Chaperon F. Fear-reducing effects of intra-amygdala neuropeptide Y infusion in animal models of conditioned fear: an NPY Y1 receptor independent effect. Psychopharmacology (Berl). 2009 Oct;206(2):291-301. doi: 10.1007/s00213-009-1610-8. Epub 2009 Jul 17. PubMed PMID: 19609506. 16: Sousa DM, Baldock PA, Enriquez RF, Zhang L, Sainsbury A, Lamghari M, Herzog H. Neuropeptide Y Y1 receptor antagonism increases bone mass in mice. Bone. 2012 Jul;51(1):8-16. doi: 10.1016/j.bone.2012.03.020. Epub 2012 Mar 28. PubMed PMID: 22484690. 17: Solway B, Bose SC, Corder G, Donahue RR, Taylor BK. Tonic inhibition of chronic pain by neuropeptide Y. Proc Natl Acad Sci U S A. 2011 Apr 26;108(17):7224-9. doi: 10.1073/pnas.1017719108. Epub 2011 Apr 11. PubMed PMID: 21482764; PubMed Central PMCID: PMC3084123. 18: Ito N, Hori A, Yabe T, Nagai T, Oikawa T, Yamada H, Hanawa T. Involvement of neuropeptide Y signaling in the antidepressant-like effect and hippocampal cell proliferation induced by kososan, a Kampo medicine, in the stress-induced depression-like model mice. Biol Pharm Bull. 2012;35(10):1775-83. PubMed PMID: 23037167. 19: Mahinda TB, Taylor BK. Intrathecal neuropeptide Y inhibits behavioral and cardiovascular responses to noxious inflammatory stimuli in awake rats. Physiol Behav. 2004 Feb;80(5):703-11. PubMed PMID: 14984805. 20: Sajdyk TJ, Schober DA, Gehlert DR. Neuropeptide Y receptor subtypes in the basolateral nucleus of the amygdala modulate anxiogenic responses in rats. Neuropharmacology. 2002 Dec;43(7):1165-72. PubMed PMID: 12504923.