ILAPRAZOLE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H18N4O2S
Molecular Weight	366.437
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=C(C)C(C[S+]([O-])C2=NC3=C(N2)C=CC(=C3)N4C=CC=C4)=NC=C1

InChI

InChIKey=HRRXCXABAPSOCP-UHFFFAOYSA-N

InChI=1S/C19H18N4O2S/c1-13-17(20-8-7-18(13)25-2)12-26(24)19-21-15-6-5-14(11-16(15)22-19)23-9-3-4-10-23/h3-11H,12H2,1-2H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula	C19H18N4O2S
Molecular Weight	366.437
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

Ilaprazole or IY-81149 (2-[(4-methoxy-3-methyl)-2-pyridinyl]methylsulfinyl -5-(1H-pyrrol-1-yl)-1H-benzimidazole, CAS 172152-36-2) is a proton pump inhibitor. Ilaprazole revealed the characteristics as a strong proton pump inhibitor, and its potency against gastric acid secretion was superior to that of the reference drug, omeprazole. Ilaprazole is approved in China and South Korea for the treatment of gastroesophageal reflux disorders (GERD), dyspepsia and peptic ulcers. Recently it was discovered that ilaprazole inhibited the cancer growth by targeting T-cell-originated protein kinase (TOPK) both in vitro and in vivo.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase 39	Inhibitor 8,297		6.0 µM [IC50]
PDZ-binding kinase 2	Inhibitor 8,297		111.0 µM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62	Primary	Preclinical	Unknown
Gastroesophageal reflux disease 59	Primary	Approved 8,429	Noltec
Peptic ulcer 72	Primary	Approved 8,429	Noltec

C_max

Value	Dose	Analyte	Population
305 ng/mL	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
293 ng/mL	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
565 ng/mL	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
638 ng/mL	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
1103 ng/mL	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
1114 ng/mL	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
834.6 ng/mL	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
836.6 ng/mL	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
482.2 ng/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
834.3 ng/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
1718.9 ng/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
347.9 ng/mL	10 mg single, oral	ILAPRAZOLE plasma	Homo sapiens
497.9 ng/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
464.25 ng/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
844.01 ng/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
824.62 ng/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
1848.9 ng/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
1570.48 ng/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
2051 ng × h/mL	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
2092 ng × h/mL	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
3948 ng × h/mL	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
4463 ng × h/mL	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
7630 ng × h/mL	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
7918 ng × h/mL	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
2774.9 ng × h/mL	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
2654.8 ng × h/mL	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
1754.8 ng × h/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3562.6 ng × h/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
7056.6 ng × h/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
1984.2 ng × h/mL	10 mg single, oral	ILAPRAZOLE plasma	Homo sapiens
2010.6 ng × h/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
1462.49 ng × h/mL	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3940.26 ng × h/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3184.85 ng × h/mL	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
8042.04 ng × h/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
5930.34 ng × h/mL	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.7 h	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
5.1 h	10 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
5.2 h	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
5.2 h	20 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
5 h	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
5.3 h	40 mg 1 times / day multiple, oral	ILAPRAZOLE plasma	Homo sapiens
2.5 h	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
2.8 h	10 mg 1 times / day steady-state, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.3 h	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.4 h	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.3 h	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.5 h	10 mg single, oral	ILAPRAZOLE plasma	Homo sapiens
3.56 h	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
2.93 h	5 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.63 h	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.22 h	10 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
3.36 h	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens
2.89 h	20 mg single, intravenous	ILAPRAZOLE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
20 mg single, intravenous Highest studied dose	healthy, ADULT	Other AEs: Activated partial thromboplastin time increased, Prothrombin time increased...
40 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT	Disc. AE: Rash... Other AEs: Erythema, Headache...

Showing 1 to 2 of 2 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Activated partial thromboplastin time increased	grade 1	20 mg single, intravenous Highest studied dose	healthy, ADULT
Prothrombin time increased	grade 1	20 mg single, intravenous Highest studied dose	healthy, ADULT
Abdominal distension	3%	40 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Headache	3%	40 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Rash	3% Disc. AE	40 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT

Showing 1 to 5 of 8 entries

Previous1 2Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2E1 667 CYP2B6 664 CYP2C19 991 CYP2A6 543 CYP3A5 395 CYP1A2 1,054 CYP2C8 693

Drug as victim

Show entries

Target	Modality	Activity
CYP1A2 1,054	substrate 3,367	likely
CYP2B6 664	substrate 3,367	likely
CYP2E1 667	substrate 3,367	likely
CYP3A4 1,737	substrate 3,367	major
CYP2C19 991	substrate 3,367	minor

Showing 1 to 5 of 10 entries

Previous1 2Next

PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

Short-term treatment of duodenal ulcer: Normally, 10 mg of adult is administered orally once a day. It is usually administered for up to 4 weeks. Short-term treatment of gastric ulcer: Normally, an adult dose of 10 mg is orally administered once a day. It is usually administered for 4 to 6 weeks. This medicine should be swallowed with water 1 hour before meals and should not be chewed or crushed. The recommended adult dosage of Ilaprazole is 5-20 mg/day.

Route of Administration: Oral

In Vitro Use Guide

Ilaprazole exhibited potent inhibitory activities against the growth of HCT116 cells (IC50 = 40 uM) and ES-2 cells (IC50 = 33.2 uM). Ilaprazole (100 and 50 uM) induces apoptosis in ES-2 and HCT116 cells.