CP-615003

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H24FN3O3
Molecular Weight	373.4213
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCNCCOC1=C(F)C=C(NC(=O)C2=CNC3=C2C(=O)CCC3)C=C1

InChI

InChIKey=YZHJISPIBWKWGY-UHFFFAOYSA-N

InChI=1S/C20H24FN3O3/c1-2-8-22-9-10-27-18-7-6-13(11-15(18)21)24-20(26)14-12-23-16-4-3-5-17(25)19(14)16/h6-7,11-12,22-23H,2-5,8-10H2,1H3,(H,24,26)

HIDE SMILES / InChI

Molecular Formula	C20H24FN3O3
Molecular Weight	373.4213
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

Description

The investigational psychopharmacologic drug candidate CP 615003 (NGD 91-3) is a potent subtype-selective partial agonist at the GABA-A receptor complex. It was designed to be fast acting without causing the sedation, memory impairment, addiction or potentiation of effects of alcohol associated with conventional anti-anxiety medication. Tissue distribution studies conducted during early clinical development of CP 615003 suggested limited brain penetration. In the Phase II clinical study, subjects tested at the high dose of NGD 91-3 showed a trend toward efficacy that did not achieve statistical significance.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38	Partial Agonist 290		1.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267	Primary		Phase II 1,132	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
173 ng/mL	100 mg 2 times / day steady-state, oral		CP-615,003 plasma	Homo sapiens
34.6 ng/mL	100 mg 2 times / day steady-state, oral		CP-900,725 plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1052 ng × h/mL	100 mg 2 times / day steady-state, oral		CP-615,003 plasma	Homo sapiens
277 ng × h/mL	100 mg 2 times / day steady-state, oral		CP-900,725 plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
100 mg 2 times / day steady-state, oral Studied dose	healthy

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Axon MedChem	1604	https://www.axonmedchem.com/product/1604
eMolecules	36367176	https://orderbb.emolecules.com/search/#?query=36367176
MolPort	MolPort-042-665-720	https://www.molport.com/shop/molecule-link/MolPort-042-665-720
Toronto Research Chemicals	K384325	https://www.trc-canada.com/product-detail/?CatNum=K384325

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PubMed

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Title	Date	PubMed
Metabolism and disposition of a gamma-aminobutyric acid type A receptor partial agonist in humans.	2008 Apr	18180269

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Patents

Sample Use Guides

In Vivo Use Guide

100 mg b.i.d.

Route of Administration: Oral

In Vitro Use Guide

The apparent permeabilities (Papp values) of CP 615003 in the absorptive direction (A to B) across parental MDCK cells were 2,8*10^6 cm/s, indicating at least moderate transcellular permeability.

Substance Class	Chemical
Record UNII	F8CYO0R7I1
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

CP-615003

Code

English

1H-INDOLE-3-CARBOXAMIDE, N-(3-FLUORO-4-(2-(PROPYLAMINO)ETHOXY)PHENYL)-4,5,6,7-TETRAHYDRO-4-OXO-

Systematic Name

English

N-(3-FLUORO-4-(2-(PROPYLAMINO)ETHOXY)PHENYL)-4,5,6,7-TETRAHYDRO-4-OXO-1H-INDOLE-3-CARBOXAMIDE

Systematic Name

English

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Code System

Code

Type

Description

WIKIPEDIA

CP-615,003

PRIMARY

FDA UNII

F8CYO0R7I1

PRIMARY

PUBCHEM

9820874

PRIMARY

EPA CompTox

DTXSID80431338

PRIMARY

CAS

329016-45-7

PRIMARY

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Related Record

Type

Details


					F8CYO0R7I1

CP-615003

EXCRETED UNCHANGED

Qualification:

URINE

Amount:

9.9 % (average)
of dose


					F8CYO0R7I1

CP-615003

EXCRETED UNCHANGED

Qualification:

FECAL

Amount:

13.6 % (average)
of dose


					6RC4EJ63I1

CP-615003 MESYLATE

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					EX926M9W3M

N-(3-FLUORO-4-(2-(2-HYDROXYETHYLAMINO)ETHOXY)PHENYL)-4-OXO-1,5,6,7-TETRAHYDROINDOLE-3-CARBOXAMIDE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:

12.4 % (average)
of Total 14C AUC0–24


					YPZ4GS5M4T

2-(2-(2-FLUORO-4-((4-OXO-1,5,6,7-TETRAHYDROINDOLE-3-CARBONYL)AMINO)PHENOXY)ETHYLAMINO)ACETIC ACID

METABOLITE -> PARENT

Qualification:

URINE

Amount:

8.7 % (average)
of dose


					NT0H1QW4F3

N-(2-(2-FLUORO-4-(((4,5,6,7-TETRAHYDRO-4-OXO-1H-INDOL-3-YL)CARBONYL)AMINO)PHENOXY)ETHYL)-N-PROPYLCARBAMIC ACID

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:

0.9 % (average)
of Total 14C AUC0–24


					YPZ4GS5M4T

2-(2-(2-FLUORO-4-((4-OXO-1,5,6,7-TETRAHYDROINDOLE-3-CARBONYL)AMINO)PHENOXY)ETHYLAMINO)ACETIC ACID

METABOLITE -> PARENT

Qualification:

FECAL

Amount:

31 % (average)
of dose


					YPZ4GS5M4T

2-(2-(2-FLUORO-4-((4-OXO-1,5,6,7-TETRAHYDROINDOLE-3-CARBONYL)AMINO)PHENOXY)ETHYLAMINO)ACETIC ACID

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:

12.8 % (average)
of Total 14C AUC0–24

Showing 1 to 5 of 6 entries

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Name	Property Type	Amount	Parameters
Biological Half-life	PHARMACOKINETIC	9.2 hours [7.1 to 11.3] (average)	P.O. ADMINISTRATION SINGLE DOSE 200 mg (average)

Tmax	PHARMACOKINETIC	1.4 hours [0.7 to 2.1] (average)	P.O. ADMINISTRATION SINGLE DOSE 200 mg (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

Doses

Sourcing

PubMed

Patents

Sample Use Guides

C_max