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Gabexato

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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

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 Formula	C₁₆H₂₃N₃O₄
Molecular Weight	321.37 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	11
Exact Mass	321.16885622 g/mol
Monoisotopic Mass	321.16885622 g/mol
Topological Polar Surface Area	117 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	400
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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