SUNEPITRON

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23N5O2
Molecular Weight	329.3968
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O=C1CCC(=O)N1C[C@H]2CC[C@H]3CN(CCN3C2)C4=NC=CC=N4

InChI

InChIKey=UXWBIYCPUVWKHP-KBPBESRZSA-N

InChI=1S/C17H23N5O2/c23-15-4-5-16(24)22(15)11-13-2-3-14-12-21(9-8-20(14)10-13)17-18-6-1-7-19-17/h1,6-7,13-14H,2-5,8-12H2/t13-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H23N5O2
Molecular Weight	329.3968
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Sunepitron (CP-93,393) is an anxiolytic drug with highly selective serotonin 5-hydroxytryptamine 1A autoreceptor agonist, alpha2-adrenergic antagonist, and dopamine D2 agonist properties. Sunepitron hydrochloride had been in Phase III clinical trials by Pfizer for the treatment of anxiety disorder and depression. However, this research has been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 114	Antagonist 2,849
Serotonin 1a (5-HT1a) receptor 177	Agonist 2,752		92.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275	Primary		Phase III 665	Unknown
Major depressive disorder 179	Primary		Withdrawn	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.02 ng/mL	5 mg single, oral		SUNEPITRON plasma	Homo sapiens
10.92 ng/mL	5 mg single, oral		SUNEPITRON plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
2.36 ng × h/mL	5 mg single, oral		SUNEPITRON plasma	Homo sapiens
87.33 ng × h/mL	5 mg single, oral		SUNEPITRON plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.9 h	5 mg single, oral		SUNEPITRON plasma	Homo sapiens
4.1 h	5 mg single, oral		SUNEPITRON plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
5 mg single, oral	healthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1,388	substrate 4,014	major

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Axon MedChem	1519	https://www.axonmedchem.com/product/1519
BOC Sciences	148408-65-5	http://www.bocsci.com/description.asp?cas=148408-65-5
Compound Cloud	183092
Compound Cloud	6918176
eMolecules	110068823	https://orderbb.emolecules.com/search/#?query=110068823

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PubMed

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Title	Date	PubMed
Metabolism and excretion of a new antianxiety drug candidate, CP-93,393, in cynomolgus monkeys: identification of the novel pyrimidine ring cleaved metabolites.	1997 Dec	9394030
Metabolism and excretion of a new anxiolytic drug candidate, CP-93, 393, in healthy male volunteers.	1998 May	9571226
Assay and purity evaluation of sunepitron hydrochloride by reversed-phase liquid chromatography using a reference standard composite.	1998 Nov	10096837
Psychopharmacology of depression in the next millennium.	1999 Jul	18438295

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Patents

Sample Use Guides

In Vivo Use Guide

The excretion, biotransformation, and pharmacokinetics of Sunepitron (CP-93,393) were investigated in six healthy male volunteers after oral administration of a 5-mg dose of [14C]CP-93,393.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	2GT50C8U60
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

CP 93393

Preferred Name

English

SUNEPITRON

Official Name

English

sunepitron [INN]

Common Name

English

CP-93,393

Code

English

2,5-PYRROLIDINEDIONE, 1-(((7S,9AS)-OCTAHYDRO-2-(2-PYRIMIDINYL)-2H-PYRIDO(1,2-A)PYRAZIN-7-YL)METHYL)-

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C47794

Adrenergic Antagonist

NCI_THESAURUS

C29713

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Code System

Code

Type

Description

WIKIPEDIA

Sunepitron

PRIMARY

EPA CompTox

DTXSID801336204

PRIMARY

CAS

131831-03-3

PRIMARY

SMS_ID

100000082983

PRIMARY

PUBCHEM

183092

PRIMARY

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Related Record

Type

Details


					UKK18ES9TF

5-HYDROXYTRYPTAMINE RECEPTOR 1A

TARGET -> AGONIST

Interaction Type:

SELECTIVE


					1NYW5HLO1E

SUNEPITRON HYDROCHLORIDE

SALT/SOLVATE -> PARENT


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR


					19GBD6T9L7

D(2) DOPAMINE RECEPTOR

TARGET -> AGONIST

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Related Record

Type

Details


					Q4J462G6Y9

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-((7S,9AS)-7-((2,5-DIOXO-1-PYRROLIDINYL)METHYL)OCTAHYDRO-2H-PYRIDO(1,2-A)PYRAZIN-2-YL)-5-PYRIMIDINYL

METABOLITE -> PARENT

Comments:

IN EXTENSIVE METABOLIZERS

Qualification:

URINE

Amount:

14.58 % (average)
of dose


					9M2JP47PFK

4-((((7R,9AS)-OCTAHYDRO-2-(2-PYRIMIDINYL)-2H-PYRIDO(1,2-A)PYRAZIN-7-YL)METHYL)AMINO)-4-OXOBUTANOIC ACID

METABOLITE -> PARENT

Comments:

IN EXTENSIVE METABOLIZERS

Qualification:

URINE

Amount:

1.19 % (average)
of dose


					Q4J462G6Y9

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-((7S,9AS)-7-((2,5-DIOXO-1-PYRROLIDINYL)METHYL)OCTAHYDRO-2H-PYRIDO(1,2-A)PYRAZIN-2-YL)-5-PYRIMIDINYL

METABOLITE -> PARENT

Comments:

IN POOR METABOLIZERS

Qualification:

PLASMA

Amount:

4.95 % (average)


					TI5X55PD2R

4-((((7R,9AS)-OCTAHYDRO-2-(5-HYDROXY-2-PYRIMIDINYL)-2H-PYRIDO(1,2-A)PYRAZIN-7-YL)METHYL)AMINO)-4-OXOBUTANOIC ACID

METABOLITE -> PARENT

Comments:

IN POOR METABOLIZERS

Qualification:

FECAL

Amount:

2.23 % (average)
of dose


					R28SQ9CZ8B

(7S,9AS)-7-((2,5-DIOXO-1-PYRROLIDINYL)METHYL)OCTAHYDRO-2H-PYRIDO(1,2-A)PYRAZINE-2-CARBOXIMIDAMIDE

METABOLITE -> PARENT

Comments:

IN EXTENSIVE METABOLIZERS

Qualification:

PLASMA

Amount:

7.16 % (average)

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Related Record

Type

Details


					2GT50C8U60

SUNEPITRON

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2