FEDOTOZINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H31NO4
Molecular Weight	373.4858
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@](COCC1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2

InChI

InChIKey=MVKIWCDXKCUDEH-QFIPXVFZSA-N

InChI=1S/C22H31NO4/c1-7-22(23(2)3,18-11-9-8-10-12-18)16-27-15-17-13-19(24-4)21(26-6)20(14-17)25-5/h8-14H,7,15-16H2,1-6H3/t22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H31NO4
Molecular Weight	373.4858
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11116283 | https://www.ncbi.nlm.nih.gov/pubmed/15989506

Fedotozine [(1R)-1-phenyl-1-[(3,4,5-trimethoxy) benzyloxymethyl]-N,N- dimethyl-n-propylamine, (2S,3S-tartrate], derived from the arylacetamide series, is an opioid drug which acts as a selective agonist for kappa(1a)-opioid receptor. Pharmacological studies have shown that fedotozine exerts a peripheral antinociceptive action, comparable with that of other kappa-agonists. Results of Phase III trials of fedotozine against irritable bowel syndrome and dyspepsia have ultimately been disappointing and was lack of efficacy in subsequent studies.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Kappa-type opioid receptor 60 Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11116283	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15989506	Primary		Phase III 656	Unknown Approved Use Unknown
Dyspepsia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15989506	Primary		Phase III 656	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
70 mg 3 times / day multiple, oral (unknown) Highest studied dose Dose: 70 mg, 3 times / day Route: oral Route: multiple Dose: 70 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8174419	unhealthy n = 31 Health Status: unhealthy Condition: Nonulcer dyspepsia Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/8174419	Other AEs: The... Other AEs: The Sources: https://pubmed.ncbi.nlm.nih.gov/8174419

AEs

AE	Significance	Dose	Population
The		70 mg 3 times / day multiple, oral (unknown) Highest studied dose Dose: 70 mg, 3 times / day Route: oral Route: multiple Dose: 70 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8174419	unhealthy n = 31 Health Status: unhealthy Condition: Nonulcer dyspepsia Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/8174419

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	133267-27-3	http://www.alfa-chemistry.com/search.aspx?q=133267-27-3
Axon MedChem	1140	https://www.axonmedchem.com/product/1140
BOC Sciences	123618-00-8	http://www.bocsci.com/description.asp?cas=123618-00-8
Hangzhou APIChem Technology	AC-19010
MolPort	MolPort-005-938-033	https://www.molport.com/shop/molecule-link/MolPort-005-938-033
MuseChem	M019241	https://www.musechem.com/product/M019241.html
MuseChem	M111148	https://www.musechem.com/product/M111148.html
eMolecules	191194098	https://orderbb.emolecules.com/search/#?query=191194098
eMolecules	275156430	https://orderbb.emolecules.com/search/#?query=275156430
eMolecules	36366940	https://orderbb.emolecules.com/search/#?query=36366940
eMolecules	36730018	https://orderbb.emolecules.com/search/#?query=36730018

PubMed

Title	Date	PubMed
Effects of fedotozine on gastrointestinal motility in dogs: mechanism of action and related pharmacokinetics.	1990 Aug	1981581
Differential effects of fedotozine compared to other kappa agonists on diuresis in rats.	1996 Dec	8968362
Novel developments with selective, non-peptidic kappa-opioid receptor agonists.	1997 Oct	15989506
Peripheral opioids for functional GI disease: a reappraisal.	2006	16699267
Inhibitory effect of the selective serotonin 5-HT₃ receptor antagonist ramosetron on duodenal acidification-induced gastric hypersensitivity in rats.	2014 May 15	24632457

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:18:47 UTC 2023` Edited by `admin` on `Fri Dec 15 17:18:47 UTC 2023`
Record UNII	F45VW2087W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEDOTOZINE

Official Name

English

(+)-(R)-.ALPHA.-ETHYL-N,N-DIMETHYL-.ALPHA.-(((3,4,5-TRIMETHOXYBENZYL)OXY)METHYL)BENZYLAMINE

Systematic Name

English

FEDOTOZINE [MI]

Common Name

English

FEDOTOZINE [MART.]

Common Name

English

fedotozine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413