L-368899

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H42N4O5S2
Molecular Weight	554.765
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC=C1N2CCN(CC2)S(=O)(=O)C[C@]34CC[C@H](C[C@@H]3NC(=O)[C@@H](N)CCS(C)(=O)=O)C4(C)C

InChI

InChIKey=MWIASLNTAGRGGA-ZJPWWDJASA-N

InChI=1S/C26H42N4O5S2/c1-19-7-5-6-8-22(19)29-12-14-30(15-13-29)37(34,35)18-26-11-9-20(25(26,2)3)17-23(26)28-24(31)21(27)10-16-36(4,32)33/h5-8,20-21,23H,9-18,27H2,1-4H3,(H,28,31)/t20-,21+,23+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C26H42N4O5S2
Molecular Weight	554.765
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22375852
Curator's Comment: description was created based on several sources, including DOI: 10.1002/ddr.430300305 Retrived from http://onlinelibrary.wiley.com/doi/10.1002/ddr.430300305/abstract

L-368,899 is a potent and selective oxytocin (OT) receptor antagonist, which was developed by Merc as a promising non peptide OT antagonist. However, this compound failed in clinical development; phase II, for the treatment of premature labour. Merck subsequently abandoned its non peptide OT antagonist program.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxytocin receptor 19 Target ID: CHEMBL2049 Sources: DOI: 10.1002/ddr.430300305 Retrived from \| http://onlinelibrary.wiley.com/doi/10.1002/ddr.430300305/abstract	Antagonist 2778		13.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Premature labour 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22375852	Preventing		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	33 mg/kg single, oral dose: 33 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		L-368899 plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
5.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
5.1 μg × h/mg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
7 μg × h/mg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	33 mg/kg single, oral dose: 33 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	L-368899 plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	L-368899 plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9321512	33 mg/kg single, oral dose: 33 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	L-368899 plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	8630	http://www.alfa-chemistry.com/search.aspx?q=8630
Alfa Chemistry	AFI148927600	http://www.alfa-chemistry.com/search.aspx?q=AFI148927600
Lan Pharmatech	LQT-B43122
Norris Pharm	NSZB-A234566
Tetrahedron	TS73444	http://www.thsci.com/search.do?q=TS73444

PubMed

Title	Date	PubMed
Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells.	1995	7475979
Pharmacokinetics and disposition of the oxytocin receptor antagonist L-368,899 in rats and dogs.	1997 Oct	9321512

Patents

Sample Use Guides

In Vivo Use Guide

in animals: rats and dog: iv dosing at 1, 2.5, and 10 mg/kg; rats and dog: oral: 5, 25, and 100 mg/kg as the tartrate salt

Route of Administration: Other

In Vitro Use Guide

L-368,899 is a potent and competitive oxytocin (OT) receptor antagonist in the rat isolated uterus (pA2, 8.9) and mouse anococcygeus muscle (pA2, 8.3) and is inactive against a number of different contractile agents in these preparations. L-368,899 also inhibits OT-stimulated phosphatidylinositol turnover in rat uterine slices and exhibits no agonist-like activity in any of the in vitro assays.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:54:27 GMT 2023` Edited by `admin` on `Sat Dec 16 04:54:27 GMT 2023`
Record UNII	ER33G946JT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-368899

Common Name

English

BUTANAMIDE, 2-AMINO-N-((1S,2S,4R)-7,7-DIMETHYL-1-(((4-(2-METHYLPHENYL)-1-PIPERAZINYL)SULFONYL)METHYL)BICYCLO(2.2.1)HEPT-2-YL)-4-(METHYLSULFONYL)-, (2S)-

Systematic Name

English

Code System Code Type Description

CAS

148927-60-0