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Synopsis

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Chemistry

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Also known as: 39492-01-8, Gabexate [inn], Ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate, Chembl87563, Ethyl p-hydroxybenzoate 6-guanidinohexanoate, Gabexate (inn)
Molecular Formula
C16H23N3O4
Molecular Weight
321.37  g/mol
InChI Key
YKGYIDJEEQRWQH-UHFFFAOYSA-N
FDA UNII
4V7M9137X9

Gabexato
A serine proteinase inhibitor used therapeutically in the treatment of pancreatitis, disseminated intravascular coagulation (DIC), and as a regional anticoagulant for hemodialysis. The drug inhibits the hydrolytic effects of thrombin, plasmin, and kallikrein, but not of chymotrypsin and aprotinin.
1 2D Structure

Gabexato

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate
2.1.2 InChI
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)
2.1.3 InChI Key
YKGYIDJEEQRWQH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC(=O)C1=CC=C(C=C1)OC(=O)CCCCCN=C(N)N
2.2 Other Identifiers
2.2.1 UNII
4V7M9137X9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Foy

2. Gabexate Mesilate

3. Gabexate Mesylate

4. Gabexate Methanesulfonate

5. Gabexate Monomethanesulfonate

6. Gabexate Monomethanesulfonate, 14c Labeled Cpd

7. Gabexate Monomethanesulfonate, 14c-labeled Cpd

8. Mesilate, Gabexate

9. Mesylate, Gabexate

10. Methanesulfonate, Gabexate

11. Monomethanesulfonate, Gabexate

2.3.2 Depositor-Supplied Synonyms

1. 39492-01-8

2. Gabexate [inn]

3. Ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate

4. Chembl87563

5. Ethyl P-hydroxybenzoate 6-guanidinohexanoate

6. Gabexate (inn)

7. 4v7m9137x9

8. Gabexato

9. Gabexatum

10. Gabexatum [inn-latin]

11. Gabexato [inn-spanish]

12. Methanesulfonic Acid Ethyl 4-[(6-carbamimidamidohexanoyl)oxy]benzoate

13. Unii-4v7m9137x9

14. Gabexate [jan]

15. Gabexate [mi]

16. Prestwick0_001008

17. Prestwick1_001008

18. Prestwick2_001008

19. Prestwick3_001008

20. Gabexate [who-dd]

21. Benzoic Acid, 4-((6-((aminoiminomethyl)amino)-1-oxohexyl)oxy)-, Ethyl Ester

22. Bspbio_001135

23. Schembl446024

24. Spbio_003016

25. Bpbio1_001249

26. Gtpl7863

27. Dtxsid9048566

28. Schembl13287301

29. Chebi:93036

30. Zinc2002226

31. Bdbm50104435

32. Db12831

33. Ethyl 4-(6-guanidinohexanoyloxy)benzoate

34. Ncgc00025297-01

35. Ncgc00025297-02

36. Ncgc00025297-10

37. Ls-14525

38. Sbi-0207080.p001

39. Ethyl 4-((6-guanidinohexanoyl)oxy)benzoate

40. Ethyl-p-(6-guanidinohex-anoyloxy)-benzoate

41. Ab00513998

42. D08004

43. Ab00513998_02

44. Q5515384

45. 4-(6-guanidino-hexanoyloxy)-benzoic Acid Ethyl Ester

46. Brd-k59256312-066-03-3

47. Ethyl 4-({6-[(diaminomethylidene)amino]hexanoyl}oxy)benzoate

48. 4-[6-(diaminomethylideneamino)-1-oxohexoxy]benzoic Acid Ethyl Ester

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 321.37 g/mol
Molecular Formula C16H23N3O4
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count11
Exact Mass321.16885622 g/mol
Monoisotopic Mass321.16885622 g/mol
Topological Polar Surface Area117 Ų
Heavy Atom Count23
Formal Charge0
Complexity400
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

No approved indication.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Gabexate bind and inhibits serine proteases in the coagulation cascade to prevent blood clotting. It also prevents proteolytic destruction of IkappaB resulting in suppression of the nuclear factor kappa-B signalling pathway. Ultimately this decreases the production of inflammatory cytokines such as tumor necrosis factor alpha which are produced as a result of NFkappaB activation.


5.2 MeSH Pharmacological Classification

Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


Serine Proteinase Inhibitors

Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)


5.3 Mechanism of Action

Gabexate inhibits kallikrein, plasmin, and thrombin by binding to their active sites. The inhibition of these components of the coagulation cascade ultimately prevents the formation of fibrin which must be present and polymerized to form a clot. Gabexate decreases the production of inflammatory cytokines by attenuating NFkappaB and c-Jun N-terminal kinase (JNK) pathway activity. The exact mechanism for this is unknown but it is thought that gabexate prevents the proteolyytic destruction of IkappaB which deactivates NFkappaB and interferes with activator protein 1 binding to DNA.


ABOUT THIS PAGE

Gabexato Manufacturers

A Gabexato manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Gabexato, including repackagers and relabelers. The FDA regulates Gabexato manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Gabexato API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Gabexato Suppliers

A Gabexato supplier is an individual or a company that provides Gabexato active pharmaceutical ingredient (API) or Gabexato finished formulations upon request. The Gabexato suppliers may include Gabexato API manufacturers, exporters, distributors and traders.

click here to find a list of Gabexato suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Gabexato JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Gabexato Drug Master File in Japan (Gabexato JDMF) empowers Gabexato API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Gabexato JDMF during the approval evaluation for pharmaceutical products. At the time of Gabexato JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Gabexato suppliers with JDMF on PharmaCompass.

Gabexato GMP

Gabexato Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Gabexato GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Gabexato GMP manufacturer or Gabexato GMP API supplier for your needs.

Gabexato CoA

A Gabexato CoA (Certificate of Analysis) is a formal document that attests to Gabexato's compliance with Gabexato specifications and serves as a tool for batch-level quality control.

Gabexato CoA mostly includes findings from lab analyses of a specific batch. For each Gabexato CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Gabexato may be tested according to a variety of international standards, such as European Pharmacopoeia (Gabexato EP), Gabexato JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Gabexato USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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