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Also known as: Upamostat, Upamostat [inn], 1191101-18-4, S5m7kw6u17, 1-piperazinecarboxylic acid, 4-((2s)-3-(3-((e)-amino(hydroxyimino)methyl)phenyl)-1-oxo-2-(((2,4,6-tris(1-methylethyl)phenyl)sulfonyl)amino)propyl)-, ethyl ester, Ethyl 4-((2s)-3-{3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate

Molecular Formula

C₃₂H₄₇N₅O₆S

Molecular Weight

629.8 g/mol

InChI Key

HUASEDVYRABWCV-NDEPHWFRSA-N

FDA UNII

S5M7KW6U17

Upamostat is an orally bioavailable, 3-amidinophenylalanine-derived, second generation serine protease inhibitor prodrug targeting the human urokinase plasminogen activator (uPA) system with potential antineoplastic and antimetastatic activities. After oral administration, upamostat is converted to the active N alpha-(2,4,6-triisopropylphenylsulfonyl)-3-amidino-(L)-phenylalanine-4-ethoxycarbonylpiperazide (WX-UK1), which inhibits several serine proteases, particularly uPA; inhibition of uPA may result in the inhibition of tumor growth and metastasis. uPA is a serine protease involved in degradation of the extracellular matrix and tumor cell migration and proliferation.

1 2D Structure

Upamostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 4-[(2S)-3-[3-[(E)-N'-hydroxycarbamimidoyl]phenyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate

2.1.2 InChI

InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34-40)35-44(41,42)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34)/t28-/m0/s1

2.1.3 InChI Key

HUASEDVYRABWCV-NDEPHWFRSA-N

2.1.4 Canonical SMILES

CCOC(=O)N1CCN(CC1)C(=O)C(CC2=CC(=CC=C2)C(=NO)N)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C

2.1.5 Isomeric SMILES

CCOC(=O)N1CCN(CC1)C(=O)[C@H](CC2=CC(=CC=C2)/C(=N\O)/N)NS(=O)(=O)C3=C(C=C(C=C3C(C)C)C(C)C)C(C)C

2.2 Other Identifiers

2.2.1 UNII

S5M7KW6U17

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Rhb-107

2. Upamostat

3. Wx-671

2.3.2 Depositor-Supplied Synonyms

1. Upamostat

2. Upamostat [inn]

3. 1191101-18-4

4. S5m7kw6u17

5. 1-piperazinecarboxylic Acid, 4-((2s)-3-(3-((e)-amino(hydroxyimino)methyl)phenyl)-1-oxo-2-(((2,4,6-tris(1-methylethyl)phenyl)sulfonyl)amino)propyl)-, Ethyl Ester

6. Ethyl 4-((2s)-3-{3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate

7. Ethyl 4-[(2s)-3-[3-[(e)-n'-hydroxycarbamimidoyl]phenyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate

8. Unii-s5m7kw6u17

9. Wx-671

10. Ethyl 4-((2s)-3-(3-((e)-n'-hydroxycarbamimidoyl)phenyl)-2-(2,3,5-tri(propan-2-yl)benzenesulfonamido)propanoyl)piperazine-1-carboxylate

11. Upamostat [who-dd]

12. Schembl12618906

13. Schembl20669283

14. 590368-25-5

15. Ex-a6355

16. Wx-671wx-671

17. Db13052

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₄₇N₅O₆S
Molecular Weight	629.8 g/mol
XLogP3	5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	12
Exact Mass	629.32470541 g/mol
Monoisotopic Mass	629.32470541 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	1070
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1