GABEXATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H23N3O4
Molecular Weight	321.3715
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=CC=C(OC(=O)CCCCCNC(N)=N)C=C1

InChI

InChIKey=YKGYIDJEEQRWQH-UHFFFAOYSA-N

InChI=1S/C16H23N3O4/c1-2-22-15(21)12-7-9-13(10-8-12)23-14(20)6-4-3-5-11-19-16(17)18/h7-10H,2-6,11H2,1H3,(H4,17,18,19)

HIDE SMILES / InChI

Molecular Formula	C16H23N3O4
Molecular Weight	321.3715
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12649382 | http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=37135 | https://www.ncbi.nlm.nih.gov/pubmed/15999923 | https://www.ncbi.nlm.nih.gov/pubmed/2442741

Gabexate is a synthetic protease inhibitor, was shown to be effective in treating patients with sepsis-associated disseminated intravascular coagulation in which tumor necrosis factor-alpha (TNF-alpha) plays a critical role. Gabexate mesylate is a drug marketed only in Italy and Japan and it is considered an essential drug in the treatment of acute pancreatitis. Gabexate is marketed under the brand name REMINARON among others in Japan. It relieves inflammatory symptoms in the pancreas by inhibiting various enzymes. It also improves organ disorders and bleeding tendency caused by blood clots in blood vessels by inhibiting blood coagulation. It is usually used to treat acute pancreatitis with deviation of proteolytic enzymes (such as trypsin, kallikrein and plasmin), acute exacerbation of chronic recurrent pancreatitis, acute pancreatitis after surgery and disseminated intravascular coagulation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nitric oxide synthase, inducible 55 Target ID: CHEMBL3051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9610382	Inhibitor 8504	5.0 mM [Ki]
Nitric oxide synthase, endothelial 5 Target ID: CHEMBL1075230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9610382	Inhibitor 8504	0.1 mM [Ki]
Kallikrein 1 2 Target ID: CHEMBL2319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9610382	Inhibitor 8504	2.6 mM [Ki]
Plasma kallikrein 9 Target ID: CHEMBL2000 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2442741 \| http://www.genome.jp/dbget-bin/www_bget?D08004	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pancreatitis 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15999923	Primary		Approved 8583	REMINARON Approved Use This medicine relieves inflammatory symptoms in the pancreas by inhibiting various enzymes. It also improves organ disorders and bleeding tendency caused by blood clots in blood vessels by inhibiting blood coagulation. It is usually used to treat acute pancreatitis with deviation of proteolytic enzymes (such as trypsin, kallikrein and plasmin), acute exacerbation of chronic recurrent pancreatitis, acute pancreatitis after surgery and disseminated intravascular coagulation.
Disseminated intravascular coagulation 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22204993 https://www.ncbi.nlm.nih.gov/pubmed/10834689	Primary		Approved 8583	REMINARON Approved Use This medicine relieves inflammatory symptoms in the pancreas by inhibiting various enzymes. It also improves organ disorders and bleeding tendency caused by blood clots in blood vessels by inhibiting blood coagulation. It is usually used to treat acute pancreatitis with deviation of proteolytic enzymes (such as trypsin, kallikrein and plasmin), acute exacerbation of chronic recurrent pancreatitis, acute pancreatitis after surgery and disseminated intravascular coagulation.

C_max

Value	Dose	Co-administered	Analyte	Population
109 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/730119_3999403D1221_1_001_1F.pdf#page=24	2 mg/kg/h 1 times / day steady-state, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: STEADY-STATE co-administered:		GABEXATE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
267 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/730119_3999403D1221_1_001_1F.pdf#page=24	2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered:		GABEXATE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
600 mg single, intravenous Studied dose Dose: 600 mg Route: intravenous Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17351806/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17351806/	Sources: https://pubmed.ncbi.nlm.nih.gov/17351806/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 MATE1 415 MATE2K 17 OCT2 779	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	inconclusive [IC50 15.8489 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMODc1NjMifX0=	inconclusive [IC50 19.9526 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMODc1NjMifX0=	no [IC50 >10 uM]
MATE1 416	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	yes [IC50 0.5 uM]
OCT2 782	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	yes [IC50 0.9 uM]
MATE2K 17	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg3NTYzIn19	yes [IC50 10.8 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3447#section=BioAssay-Results Page: 48 \| 49	no

PubMed

Title	Date	PubMed
Continuous regional arterial infusion therapy with gabexate mesilate for severe acute pancreatitis.	2008-11-07	19009656
Selective inhibition of human mast cell tryptase by gabexate mesylate, an antiproteinase drug.	2001-02-01	11172730

Patents

Sample Use Guides

In Vivo Use Guide

Prevention of post-endoscopic retrograde cholangiopancreatography pancreatitis: continuous intravenous infusion (600 mg)

Route of Administration: Intravenous

In Vitro Use Guide

The LPS-induced increase in TNF-a production by human monocytes was significantly inhibited by gabexate mesilate at a concentration of 1.0 x10(-3) M.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:52:55 GMT 2025` Edited by `admin` on `Wed Apr 02 06:52:55 GMT 2025`
Record UNII	4V7M9137X9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GABEXATE

Official Name

English

GABEXATE [MI]

Preferred Name

English

GABEXATE [JAN]

Common Name

English

gabexate [INN]

Common Name

English

Gabexate [WHO-DD]

Common Name

English

ETHYL P-HYDROXYBENZOATE 6-GUANIDINOHEXANOATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C263