FENCLONINE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H10ClNO2
Molecular Weight	199.634
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC(CC1=CC=C(Cl)C=C1)C(O)=O

InChI

InChIKey=NIGWMJHCCYYCSF-UHFFFAOYSA-N

InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

HIDE SMILES / InChI

Molecular Formula	C9H10ClNO2
Molecular Weight	199.634
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Fenclonine, also known as p-chlorophenylalanine, is an inhibitor of tryptophan hydroxylase, the enzyme that plays a rate-limiting role in the biosynthesis of serotonin. Fenclonine was studied for the treatment of carcinoid syndrome, but the psychological side effects, prevented for the further development for this use.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CHEMBL3831287: Tryptophan 5-hydroxylase 2	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Carcinoid syndrome 6	Primary		Withdrawn	Unknown

PubMed

Show entries

Title	Date	PubMed
Role of monoamine oxidase inhibition and monoamine depletion in fenfluramine-induced neurotoxicity and serotonin release.	2001 Nov	11881977
p-Chlorophenylalanine eliminates long-term modulation of the exercise ventilatory response in goats.	2001 Nov 1	11812380
Self-biting induced by activation of L-type calcium channels in mice: serotonergic influences.	2002	12457070
Assessment of spinal cord pathology following trauma using early changes in the spinal cord evoked potentials: a pharmacological and morphological study in the rat.	2002	12116291
Lack of 5-HT(1B) receptor and of serotonin transporter have different effects on the segregation of retinal axons in the lateral geniculate nucleus compared to the superior colliculus.	2002	12031347

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Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	R5J7E3L9SP
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

FENCLONINE

Official Name

English

CP-10188

Code

English

NSC-77370

Code

English

fenclonine [INN]

Common Name

English

FENCLONINE [HSDB]

Common Name

English

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Classification Tree

Code System

Code

Pharmacologic Substance

NCI_THESAURUS

C471

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Code System

Code

Type

Description

INN

2382

PRIMARY

WIKIPEDIA

FENCLONINE

PRIMARY

SMS_ID

100000081268

PRIMARY

CAS

7424-00-2

PRIMARY

NCI_THESAURUS

C81112

PRIMARY

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Related Record

Type

Details


					P5RI31WVDB

TRYPTOPHAN 5-HYDROXYLASE 1

TARGET -> INHIBITOR

Comments:

In vivo it is a potent and irreversible inhibitor of TPH (and PAH) that increases phenylalanine levels and rapidly depletes serotonin from the nervous system

Interaction Type:

IRREVERSIBLE INHIBITOR

Qualification:

IC50

Amount:

250 MICROMOLAR (average)