Ufiprazole

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19N3O2S
Molecular Weight	329.417
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(NC(SCC3=NC=C(C)C(OC)=C3C)=N2)C=C1

InChI

InChIKey=XURCIPRUUASYLR-UHFFFAOYSA-N

InChI=1S/C17H19N3O2S/c1-10-8-18-15(11(2)16(10)22-4)9-23-17-19-13-6-5-12(21-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C17H19N3O2S
Molecular Weight	329.417
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=7&ved=0ahUKEwi2wb7MyMLXAhURIuwKHS4iCLMQFghJMAY&url=https%3A%2F%2Fkuscholarworks.ku.edu%2Fbitstream%2Fhandle%2F1808%2F19459%2FOgilvie_ku_0099D_13918_DATA_1.pdf%3Bsequence%3D1&usg=AOvVaw3VOYBeS-_felBOQniqTuz_ | https://www.ncbi.nlm.nih.gov/pubmed/18818070

Ufiprazole (Omeprazole sulfide) is a metabolite of Omeprazole, which is a proton pump inhibitor. Omeprazole sulfide has been shown to be a direct-acting inhibitor of CYP2C19 in pooled human liver microsomes. Ufiprazole is also a weak BRS-3 agonist.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bombesin receptor subtype-3 2 Target ID: CHEMBL4080 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18818070	Partial Agonist 297		3.9 µM [EC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=7&ved=0ahUKEwi2wb7MyMLXAhURIuwKHS4iCLMQFghJMAY&url=https%3A%2F%2Fkuscholarworks.ku.edu%2Fbitstream%2Fhandle%2F1808%2F19459%2FOgilvie_ku_0099D_13918_DATA_1.pdf%3Bsequence%3D1&usg=AOvVaw3VOYBeS-_felBOQniqTuz_	Inhibitor 8504		9.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Regioselective C-H hydroxylation of omeprazole sulfide by Bacillus megaterium CYP102A1 to produce a human metabolite.	2017-01	27640009
Solubility of Omeprazole Sulfide in Different Solvents at the Range of 280.35-319.65 K.	2013	24319302
Role of CYP3A4 in the regulation of the aryl hydrocarbon receptor by omeprazole sulphide.	2006-05	16109480

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Omeprazole sulfide was evaluated as direct-acting and MDI of CYP2C19 activity (S-mephenytoin 4´-hydroxylation) in pooled human liver microsomes (0.1 mg/mL) at a substrate concentration approximately equal to the Km (40 uM). Omeprazole sulfide has been shown to be a direct-acting inhibitor of CYP2C19 in pooled human liver microsomes with IC50 value of 9.7 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:59:33 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:33 GMT 2025`
Record UNII	6FFV1V867C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Ufiprazole

Official Name

English

OMEPRAZOLE IMPURITY C [EP IMPURITY]

Preferred Name

English

OMEPRAZOLE MAGNESIUM IMPURITY C [EP IMPURITY]

Common Name

English

ufiprazole [INN]

Common Name

English

OMEPRAZOLE SULFIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29723