3-(2-(1-(CYCLOHEXYLMETHYL)-2-OXO-1H,2H,5H,6H,7H,8H,9H,10H-CYCLOOCTA(B)PYRIDINE-3-AMIDO)-1,3-THIAZOL-4-YL)PROPANOIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H33N3O4S
Molecular Weight	471.612
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3-(2-(1-(CYCLOHEXYLMETHYL)-2-OXO-1H,2H,5H,6H,7H,8H,9H,10H-CYCLOOCTA(B)PYRIDINE-3-AMIDO)-1,3-THIAZOL-4-YL)PROPANOIC ACID

SMILES

OC(=O)CCC1=CSC(NC(=O)C2=CC3=C(CCCCCC3)N(CC4CCCCC4)C2=O)=N1

InChI

InChIKey=SYBONVBDFTYUQP-UHFFFAOYSA-N

InChI=1S/C25H33N3O4S/c29-22(30)13-12-19-16-33-25(26-19)27-23(31)20-14-18-10-6-1-2-7-11-21(18)28(24(20)32)15-17-8-4-3-5-9-17/h14,16-17H,1-13,15H2,(H,29,30)(H,26,27,31)

HIDE SMILES / InChI

Molecular Formula	C25H33N3O4S
Molecular Weight	471.612
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Substance Class	Chemical
Record UNII	NVJ8QDQ4QW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-(2-(1-(CYCLOHEXYLMETHYL)-2-OXO-1H,2H,5H,6H,7H,8H,9H,10H-CYCLOOCTA(B)PYRIDINE-3-AMIDO)-1,3-THIAZOL-4-YL)PROPANOIC ACID

Systematic Name

English

S-444823

Code

English

2-(((1-(CYCLOHEXYLMETHYL)-1,2,5,6,7,8,9,10-OCTAHYDRO-2-OXOCYCLOOCTA(B)PYRIDIN-3-YL)CARBONYL)AMINO)-4-THIAZOLEPROPANOIC ACID

Systematic Name

English

4-THIAZOLEPROPANOIC ACID, 2-(((1-(CYCLOHEXYLMETHYL)-1,2,5,6,7,8,9,10-OCTAHYDRO-2-OXOCYCLOOCTA(B)PYRIDIN-3-YL)CARBONYL)AMINO)-

Systematic Name

English

S444823

Code

English

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Code System

Code

Type

Description

CAS

885490-15-3

PRIMARY

WIKIPEDIA

S-444,823

PRIMARY

EPA CompTox

DTXSID001030400

PRIMARY

PUBCHEM

57387465

PRIMARY

FDA UNII

NVJ8QDQ4QW

PRIMARY

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Related Record

Type

Details


					NVJ8QDQ4QW

3-(2-(1-(CYCLOHEXYLMETHYL)-2-OXO-1H,2H,5H,6H,7H,8H,9H,10H-CYCLOOCTA(B)PYRIDINE-3-AMIDO)-1,3-THIAZOL-4-YL)PROPANOIC ACID

ACTIVE MOIETY

Comments:

Among them, compounds 19 and 21 showed potent affinities for CB receptors and displayed the strong inhibition of scratching induced by compound 48/80 without CNS side effects caused from activating CB1 receptor. These efforts led to the discovery of clinical candidate 21, S-444823, as the agent for atopic diseases. Following data is for S-444823: Kia (hCB1) = 580(nM); Kia (hCB2) = 18(nM); IC50 = 454(nM)for CB1(cAMP)b; IC50 = 15(nM) for CB2(cAMP)b


					NVJ8QDQ4QW

3-(2-(1-(CYCLOHEXYLMETHYL)-2-OXO-1H,2H,5H,6H,7H,8H,9H,10H-CYCLOOCTA(B)PYRIDINE-3-AMIDO)-1,3-THIAZOL-4-YL)PROPANOIC ACID

ACTIVE MOIETY

Comments:

Originator: Shionogi; Class: Antipruritic, Skin disorder therapy; Mechanism of Action: Cannabinoid receptor agonist; Highest Development Phase: Discontinued for Atopic dermatitis; Most Recent Event: 01 Jan 2010 Phase-II clinical trials in Atopic dermatitis in Japan (Topical) (JapicCTI100996)

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