Talnetant
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MedKoo CAT#: 526414

CAS#: 174636-32-9

Description: Talnetant is a novel NK3 receptor antagonist.

Chemical Structure

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Talnetant
CAS# 174636-32-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526414
Name: Talnetant
CAS#: 174636-32-9
Chemical Formula: C25H22N2O2
Exact Mass: 382.17
Molecular Weight: 382.463
Elemental Analysis: C, 78.51; H, 5.80; N, 7.32; O, 8.37

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 2 Weeks
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Synonym: Talnetant

IUPAC/Chemical Name: 3-hydroxy-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

InChi Key: BIAVGWDGIJKWRM-FQEVSTJZSA-N

InChi Code: InChI=1S/C25H22N2O2/c1-2-20(17-11-5-3-6-12-17)27-25(29)22-19-15-9-10-16-21(19)26-23(24(22)28)18-13-7-4-8-14-18/h3-16,20,28H,2H2,1H3,(H,27,29)/t20-/m0/s1

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

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
Certificate of Analysis:
View CoA: current batch, Lot#C22M08C19
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Talnetant (SB 223412) is a selective, competitive, brain-permeable NK3 receptor antagonist with a Ki of 1.4 nM in hNK-3-CHO cells.
In vitro activity: SB 223412 demonstrated enantioselective affinity for inhibition of [125I][MePhe7]neurokinin B (NKB) binding to membranes of CHO cells expressing the hNK-3 receptor (CHO hNK-3). SB 223412, the (S)-isomer, (Ki = 1.0 nM), has similar affinity as the natural ligand, NKB (Ki = 0.8 nM) and another nonpeptide NK-3 receptor antagonist, SR 142801 (Ki = 1.2 nM). SB 223412 was selective for hNK-3 receptors compared with hNK-1 (>10,000-fold selective) and hNK-2 receptors (>140-fold selective), and selectivity was further demonstrated by its lack of effect, in concentrations up to 1 or 10 microM, in >60 receptor, enzyme and ion channel assays. SB 223412 enantioselectively inhibited the NKB-induced Ca++ mobilization in HEK 293 cells stably expressing the hNK-3 receptor. Reference: J Pharmacol Exp Ther. 1997 Jun;281(3):1303-11. https://pubmed.ncbi.nlm.nih.gov/9190866/
In vivo activity: Intravenous infusion or oral administration of SB223412, a selective NK3R antagonist, exerts a suppressive effect on GnRH pulse generator activity in E2-treated OVX goats. Intravenous infusion of the NK3R antagonist led to an increase in intervals of MUA volley, an electrophysiological manifestation of GnRH pulse generator activity, as well as interpulse intervals of LH pulses. The results suggest that peripheral administration of the NK3R antagonist suppressed pulsatile LH secretion by acting on the GnRH pulse generator. Reference: J Reprod Dev. 2020 Aug 20;66(4):351-357. https://pubmed.ncbi.nlm.nih.gov/32281549/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 62.5 163.41

Preparing Stock Solutions

The following data is based on the product molecular weight 382.46 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. Sarau HM, Griswold DE, Potts W, Foley JJ, Schmidt DB, Webb EF, Martin LD, Brawner ME, Elshourbagy NA, Medhurst AD, Giardina GA, Hay DW. Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist. J Pharmacol Exp Ther. 1997 Jun;281(3):1303-11. PMID: 9190866. 2. Sasaki T, Sonoda T, Tatebayashi R, Kitagawa Y, Oishi S, Yamamoto K, Fujii N, Inoue N, Uenoyama Y, Tsukamura H, Maeda KI, Matsuda F, Morita Y, Matsuyama S, Ohkura S. Peripheral administration of SB223412, a selective neurokinin-3 receptor antagonist, suppresses pulsatile luteinizing hormone secretion by acting on the gonadotropin-releasing hormone pulse generator in estrogen-treated ovariectomized female goats. J Reprod Dev. 2020 Aug 20;66(4):351-357. doi: 10.1262/jrd.2019-145. Epub 2020 Apr 12. PMID: 32281549; PMCID: PMC7470901.
In vitro protocol: 1. Sarau HM, Griswold DE, Potts W, Foley JJ, Schmidt DB, Webb EF, Martin LD, Brawner ME, Elshourbagy NA, Medhurst AD, Giardina GA, Hay DW. Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist. J Pharmacol Exp Ther. 1997 Jun;281(3):1303-11. PMID: 9190866.
In vivo protocol: 1. Sasaki T, Sonoda T, Tatebayashi R, Kitagawa Y, Oishi S, Yamamoto K, Fujii N, Inoue N, Uenoyama Y, Tsukamura H, Maeda KI, Matsuda F, Morita Y, Matsuyama S, Ohkura S. Peripheral administration of SB223412, a selective neurokinin-3 receptor antagonist, suppresses pulsatile luteinizing hormone secretion by acting on the gonadotropin-releasing hormone pulse generator in estrogen-treated ovariectomized female goats. J Reprod Dev. 2020 Aug 20;66(4):351-357. doi: 10.1262/jrd.2019-145. Epub 2020 Apr 12. PMID: 32281549; PMCID: PMC7470901.

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1: Yamamoto K, Okazaki S, Ohno H, Matsuda F, Ohkura S, Maeda K, Fujii N, Oishi S. Development of novel NK3 receptor antagonists with reduced environmental impact. Bioorg Med Chem. 2016 Aug 15;24(16):3494-500. doi: 10.1016/j.bmc.2016.05.054. PubMed PMID: 27298001.

2: Corsetti M, Akyuz F, Tack J. Targeting tachykinin receptors for the treatment of functional gastrointestinal disorders with a focus on irritable bowel syndrome. Neurogastroenterol Motil. 2015 Oct;27(10):1354-70. doi: 10.1111/nmo.12616. Review. PubMed PMID: 26088804.

3: Malherbe P, Knoflach F, Marcuz A, Bohnert C, Weber M, Knust H, Ratni H, Spooren W, Ballard TM, Bissantz C. Mapping the binding pocket of a novel, high-affinity, slow dissociating tachykinin NK3 receptor antagonist: biochemical and electrophysiological characterization. Neuropharmacology. 2014 Nov;86:259-72. doi: 10.1016/j.neuropharm.2014.07.017. PubMed PMID: 25107588.

4: Nakamura A, Tanaka T, Imanishi A, Kawamoto M, Toyoda M, Mizojiri G, Tsukimi Y. Bidirectional regulation of human colonic smooth muscle contractility by tachykinin NK(2) receptors. J Pharmacol Sci. 2011;117(2):106-15. PubMed PMID: 21946672.

5: Malherbe P, Ballard TM, Ratni H. Tachykinin neurokinin 3 receptor antagonists: a patent review (2005 - 2010). Expert Opin Ther Pat. 2011 May;21(5):637-55. doi: 10.1517/13543776.2011.568482. Review. PubMed PMID: 21417773.

6: Noritake K, Suzuki J, Matsuoka T, Makino T, Ohnishi H, Shimomura K, Uenoyama Y, Tsukamura H, Maeda K, Sanbuissho A. Testicular toxicity induced by a triple neurokinin receptor antagonist in male dogs. Reprod Toxicol. 2011 May;31(4):440-6. doi: 10.1016/j.reprotox.2010.12.007. PubMed PMID: 21185367.

7: Geldenhuys WJ, Kuzenko SR, Simmons MA. Virtual screening to identify novel antagonists for the G protein-coupled NK3 receptor. J Med Chem. 2010 Nov 25;53(22):8080-8. doi: 10.1021/jm1010012. PubMed PMID: 21047106.

8: Malherbe P, Knoflach F, Hernandez MC, Hoffmann T, Schnider P, Porter RH, Wettstein JG, Ballard TM, Spooren W, Steward L. Characterization of RO4583298 as a novel potent, dual antagonist with in vivo activity at tachykinin NK₁ and NK₃ receptors. Br J Pharmacol. 2011 Feb;162(4):929-46. doi: 10.1111/j.1476-5381.2010.01096.x. PubMed PMID: 21039418; PubMed Central PMCID: PMC3042203.

9: Corboz MR, Rivelli MA, Eckel SP. Bronchoconstrictor effect of the tachykinin NK₃-receptor agonists [MePhe⁷]-neurokinin B and senktide in the isolated guinea pig lung. Exp Lung Res. 2010 Nov;36(9):509-21. doi: 10.3109/01902141003777582. PubMed PMID: 20939761.

10: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jun;32(5):331-88. doi: 10.1358/mf.2010.32.5.1520420. PubMed PMID: 20664824.

11: Rohbogner CJ, Wirth S, Knochel P. Phosphorodiamidate-directed metalation of N-heterocycles using Mg- and Zn-TMP bases. Org Lett. 2010 May 7;12(9):1984-7. doi: 10.1021/ol100453x. PubMed PMID: 20356104.

12: Malherbe P, Kratzeisen C, Marcuz A, Zenner MT, Nettekoven MH, Ratni H, Wettstein JG, Bissantz C. Identification of a critical residue in the transmembrane domain 2 of tachykinin neurokinin 3 receptor affecting the dissociation kinetics and antagonism mode of osanetant (SR 142801) and piperidine-based structures. J Med Chem. 2009 Nov 26;52(22):7103-12. doi: 10.1021/jm900948q. PubMed PMID: 19817444.

13: Nordquist RE, Ballard TM, Algeyer B, Pauly-Evers M, Ozmen L, Spooren W. Pharmacological characterization of senktide-induced tail whips. Neuropharmacology. 2010 Jan;58(1):259-67. doi: 10.1016/j.neuropharm.2009.04.018. PubMed PMID: 19540857.

14: Smith PW, Wyman PA, Lovell P, Goodacre C, Serafinowska HT, Vong A, Harrington F, Flynn S, Bradley DM, Porter R, Coggon S, Murkitt G, Searle K, Thomas DR, Watson JM, Martin W, Wu Z, Dawson LA. New quinoline NK3 receptor antagonists with CNS activity. Bioorg Med Chem Lett. 2009 Feb 1;19(3):837-40. doi: 10.1016/j.bmcl.2008.12.005. PubMed PMID: 19117759.

15: Nordquist RE, Durkin S, Jacquet A, Spooren W. The tachykinin NK3 receptor agonist senktide induces locomotor activity in male Mongolian gerbils. Eur J Pharmacol. 2008 Dec 14;600(1-3):87-92. doi: 10.1016/j.ejphar.2008.10.011. PubMed PMID: 18930726.

16: de la Flor R, Dawson LA. Augmentation of antipsychotic-induced neurochemical changes by the NK3 receptor antagonist talnetant (SB-223412). Neuropharmacology. 2009 Feb;56(2):342-9. doi: 10.1016/j.neuropharm.2008.09.003. PubMed PMID: 18822303.

17: Liem-Moolenaar M, Gray FA, de Visser SJ, Franson KL, Schoemaker RC, Schmitt JA, Cohen AF, van Gerven JM. Psychomotor and cognitive effects of a single oral dose of talnetant (SB223412) in healthy volunteers compared with placebo or haloperidol. J Psychopharmacol. 2010 Jan;24(1):73-82. doi: 10.1177/0269881108094524. PubMed PMID: 18755817.

18: Malherbe P, Bissantz C, Marcuz A, Kratzeisen C, Zenner MT, Wettstein JG, Ratni H, Riemer C, Spooren W. Me-talnetant and osanetant interact within overlapping but not identical binding pockets in the human tachykinin neurokinin 3 receptor transmembrane domains. Mol Pharmacol. 2008 Jun;73(6):1736-50. doi: 10.1124/mol.107.042754. PubMed PMID: 18308898.

19: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Oct;29(8):547-83. PubMed PMID: 18040531.

20: Boudet N, Lachs JR, Knochel P. Multiple regioselective functionalizations of quinolines via magnesiations. Org Lett. 2007 Dec 20;9(26):5525-8. PubMed PMID: 18027959.