Osanetant

Osanetant
Clinical data
ATC code	none;
Identifiers
	IUPAC name N-(1-{3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl}-4-phenylpiperidin-4-yl]-N-methylacetamide;
CAS Number	160492-56-8 ;
PubChem CID	219077;
IUPHAR/BPS	2110;
ChemSpider	189901 ;
UNII	K7G81N94DT;
ChEMBL	ChEMBL346178 ;
ECHA InfoCard	100.233.307
Chemical and physical data
Formula	C35H41Cl2N3O2
Molar mass	606.63 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)N(C)C1(CCN(CC1)CCC[C@@]2(CCCN(C2)C(=O)C3=CC=CC=C3)C4=CC(=C(C=C4)Cl)Cl)C5=CC=CC=C5;
	InChI InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1 ; Key:DZOJBGLFWINFBF-UMSFTDKQSA-N ;
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Osanetant (developmental code name SR-142,801) is a neurokinin 3 receptor antagonist which was developed by Sanofi-Synthélabo and was being researched for the treatment of schizophrenia but was discontinued.^[1]^[2] It was the first non-peptide NK₃ antagonist developed in the mid-1990s,^[3]^[4] Other potential applications for osanetant is in the treatment of drug addiction, as it has been found to block the effects of cocaine in animal models.^[5]^[6]

References[]

^ "osanetant Sanofi-Aventis discontinued, France". Highbeam. Archived from the original on 2016-03-11.
^ Kamali F (July 2001). "Osanetant Sanofi-Synthélabo". Current Opinion in Investigational Drugs. 2 (7): 950–6. PMID 11757797.
^ Emonds-Alt X, Bichon D, Ducoux JP, Heaulme M, Miloux B, Poncelet M, et al. (1995). "SR 142801, the first potent non-peptide antagonist of the tachykinin NK3 receptor". Life Sciences. 56 (1): PL27-32. doi:10.1016/0024-3205(94)00413-M. PMID 7830490.
^ Quartara L, Altamura M (August 2006). "Tachykinin receptors antagonists: from research to clinic". Current Drug Targets. 7 (8): 975–92. doi:10.2174/138945006778019381. PMID 16918326. Archived from the original on 2011-07-25.
^ De Souza Silva MA, Mello EL, Müller CP, Jocham G, Maior RS, Huston JP, et al. (May 2006). "The tachykinin NK3 receptor antagonist SR142801 blocks the behavioral effects of cocaine in marmoset monkeys". European Journal of Pharmacology. 536 (3): 269–78. doi:10.1016/j.ejphar.2006.03.010. PMID 16603151.
^ Jocham G, Lezoch K, Müller CP, Kart-Teke E, Huston JP, de Souza Silva MA (September 2006). "Neurokinin receptor antagonism attenuates cocaine's behavioural activating effects yet potentiates its dopamine-enhancing action in the nucleus accumbens core". The European Journal of Neuroscience. 24 (6): 1721–32. doi:10.1111/j.1460-9568.2006.05041.x. PMID 17004936. S2CID 29488484.

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[1] "osanetant Sanofi-Aventis discontinued, France". Highbeam. Archived from the original on 2016-03-11.

[2] Kamali F (July 2001). "Osanetant Sanofi-Synthélabo". Current Opinion in Investigational Drugs. 2 (7): 950–6. PMID 11757797.

[3] Emonds-Alt X, Bichon D, Ducoux JP, Heaulme M, Miloux B, Poncelet M, et al. (1995). "SR 142801, the first potent non-peptide antagonist of the tachykinin NK3 receptor". Life Sciences. 56 (1): PL27-32. doi:10.1016/0024-3205(94)00413-M. PMID 7830490.

[pmid16918326-4] Quartara L, Altamura M (August 2006). "Tachykinin receptors antagonists: from research to clinic". Current Drug Targets. 7 (8): 975–92. doi:10.2174/138945006778019381. PMID 16918326. Archived from the original on 2011-07-25.

[5] De Souza Silva MA, Mello EL, Müller CP, Jocham G, Maior RS, Huston JP, et al. (May 2006). "The tachykinin NK3 receptor antagonist SR142801 blocks the behavioral effects of cocaine in marmoset monkeys". European Journal of Pharmacology. 536 (3): 269–78. doi:10.1016/j.ejphar.2006.03.010. PMID 16603151.

[6] Jocham G, Lezoch K, Müller CP, Kart-Teke E, Huston JP, de Souza Silva MA (September 2006). "Neurokinin receptor antagonism attenuates cocaine's behavioural activating effects yet potentiates its dopamine-enhancing action in the nucleus accumbens core". The European Journal of Neuroscience. 24 (6): 1721–32. doi:10.1111/j.1460-9568.2006.05041.x. PMID 17004936. S2CID 29488484.

[1]

[2]

[3]

[4]

[5]

[6]

v t Neurokinin receptor modulators
NK₁	Agonists: Substance P Antagonists: Aprepitant Befetupitant Burapitant Casopitant Elinzanetant Ezlopitant Fosaprepitant Fosnetupitant L-733,060 Lanepitant Maropitant Netupitant Orvepitant Rolapitant Serlopitant Tradipitant Vestipitant Vofopitant
NK₂	Agonists: Neurokinin A Antagonists: GR-159897 Ibodutant Nepadutant Saredutant
NK₃	Agonists: Neurokinin B Antagonists: Elinzanetant Fezolinetant (ESN-364) Osanetant (SR-142,801) Pavinetant (MLE-4901, AZD-2624, AZD-4901) Talnetant (SB-223,412)

Clinical data

ATC code	none
Identifiers
IUPAC name N-(1-{3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl}-4-phenylpiperidin-4-yl]-N-methylacetamide
CAS Number	160492-56-8^Y
PubChem CID	219077
IUPHAR/BPS	2110
ChemSpider	189901^N
UNII	K7G81N94DT
ChEMBL	ChEMBL346178^N
ECHA InfoCard	100.233.307
Chemical and physical data
Formula	C₃₅H₄₁Cl₂N₃O₂
Molar mass	606.63 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)N(C)C1(CCN(CC1)CCC[C@@]2(CCCN(C2)C(=O)C3=CC=CC=C3)C4=CC(=C(C=C4)Cl)Cl)C5=CC=CC=C5
InChI InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1^N Key:DZOJBGLFWINFBF-UMSFTDKQSA-N^N
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