FEZOLINETANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15FN6OS
Molecular Weight	358.393
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

C[C@H]1N(CCN2C1=NN=C2C3=NC(C)=NS3)C(=O)C4=CC=C(F)C=C4

InChI

InChIKey=PPSNFPASKFYPMN-SECBINFHSA-N

InChI=1S/C16H15FN6OS/c1-9-13-19-20-14(15-18-10(2)21-25-15)23(13)8-7-22(9)16(24)11-3-5-12(17)6-4-11/h3-6,9H,7-8H2,1-2H3/t9-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H15FN6OS
Molecular Weight	358.393
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Fezolinetant (ESN-364) is an antagonist of the neurokinin-3 receptor. It suppresses the hypothalamic-pituitary-gonadal axis. Ogeda is developing fezolinetant for the treatment of hot flashes (vasomotor symptoms) in postmenopausal women.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Neuromedin-K receptor 1	Antagonist 2,778		7.6 null [pKi]

PubMed

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Title	Date	PubMed
Optimization of Novel Antagonists to the Neurokinin-3 Receptor for the Treatment of Sex-Hormone Disorders (Part II).	2015 Jul 9	26191358
The NK3 Receptor Antagonist ESN364 Interrupts Pulsatile LH Secretion and Moderates Levels of Ovarian Hormones Throughout the Menstrual Cycle.	2015 Nov	26305889
The NK3 Receptor Antagonist ESN364 Suppresses Sex Hormones in Men and Women.	2016 Feb	26653113

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Patents

Sample Use Guides

In Vivo Use Guide

Phase 2 study for the treatment of hot flashes (vasomotor symptoms) in postmenopausal women. The dose of ESN364 varies across 7 treatment groups, with groups receiving once a day or twice a day blinded study drug. Doses range from 30 mg to 180 mg total daily dosing for 12 weeks.

Route of Administration: Oral

Substance Class	Chemical
Record UNII	83VNE45KXX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEZOLINETANT

Official Name

English

AS-3472693-00

Code

English

(4-FLUOROPHENYL)((8R)-8-METHYL-3-(3-METHYL-1,2,4- THIADIAZOL-5-YL)-5,6-DIHYDRO-1,2,4-TRIAZOLO(4,3-A)PYRAZIN- 7(8H)-YL)METHANONE

Systematic Name

English

FEZOLINETANT [USAN]

Common Name

English

METHANONE, ((8R)-5,6-DIHYDRO-8-METHYL-3-(3-METHYL-1,2,4-THIADIAZOL-5-YL)-1,2,4-TRIAZOLO(4,3-A)PYRAZIN-7(8H)-YL)(4-FLUOROPHENYL)-

Systematic Name

English

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Code System

Code

Type

Description

USAN

HI-226

PRIMARY

NCI_THESAURUS

C171845

PRIMARY

DRUG BANK

DB15669

PRIMARY

WIKIPEDIA

FEZOLINETANT

PRIMARY

PUBCHEM

117604931

PRIMARY

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Related Record

Type

Details


					8JDV78GMR7

NEUROMEDIN-K RECEPTOR

TARGET -> INHIBITOR

Amount:

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Related Record

Type

Details


					83VNE45KXX

FEZOLINETANT

ACTIVE MOIETY

Comments:

INTERVENTION(S): In part 1 of the study, men received single oral doses of 3-180 mg or placebo. In part 2, men received placebo or 20, 60, or 180 mg each day for 10 days. In part 3, women received placebo or 20, 60, or 180 mg each day for 21 days, where dosing was initiated on day 3 +/- 2 after menses. RESULTS: ESN364 was well-tolerated and rapidly bioavailable with linear pharmacokinetics and no drug accumulation with repeated, daily oral administration. Drug treatment dose-dependently decreased basal LH, but not FSH, and consequently decreased estradiol and progesterone (in women) as well as testosterone (in men). The hormonal changes in women corresponded to delayed ovulation, decreased endometrial thickening, impeded follicular maturation, and prolongation of the menstrual cycle. Drug effects were rapidly reversible. CONCLUSIONS: Oral administration of the NK3R antagonist, ESN364, suppressed the hypothalamic-pituitary-gonadal axis in healthy volunteers by selective modulation of gonadotropin secretion, leading to a restrained decrease in ovarian hormone levels in women. These results suggest that ESN364 may offer therapeutic benefit in the treatment of women's health disorders with a mitigated risk of menopausal-like adverse events.

Amount:

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