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Razuprotafib

Razuprotafib

Synopsis, Chemistry

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Also known as: 1008510-37-9, Akb-9778, Razuprotafib [inn], Razuprotafib [usan], 0wax4ut396, Razuprotafib (usan)

Molecular Formula

C₂₆H₂₆N₄O₆S₃

Molecular Weight

586.7 g/mol

InChI Key

KWJDHELCGJFUHW-SFTDATJTSA-N

FDA UNII

0WAX4UT396

Razuprotafib is a small molecule inhibitor of vascular endothelial protein tyrosine phosphatase (VE-PTP), with potential vasculature stabilizing activity. Upon administration, razuprotafib targets, binds to and inhibits VE-PTP, which is a negative regulator of the endothelial cell (EC)-specific receptor tyrosine kinase (RTK) Tie2. This restores Tie2 activation, which may improve endothelial function and stabilize blood vessels. VE-PTP is upregulated in stressed endothelium associated with a variety of diseases. Tie2 plays an important role in endothelial function and vascular stability. A decrease in Tie2 activation leads to vascular leakage and inflammation.

1 2D Structure

Razuprotafib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[(2S)-2-[[(2S)-2-(methoxycarbonylamino)-3-phenylpropanoyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid

2.1.2 InChI

InChI=1S/C26H26N4O6S3/c1-36-26(32)29-21(15-17-6-3-2-4-7-17)24(31)27-20(22-16-38-25(28-22)23-8-5-13-37-23)14-18-9-11-19(12-10-18)30-39(33,34)35/h2-13,16,20-21,30H,14-15H2,1H3,(H,27,31)(H,29,32)(H,33,34,35)/t20-,21-/m0/s1

2.1.3 InChI Key

KWJDHELCGJFUHW-SFTDATJTSA-N

2.1.4 Canonical SMILES

COC(=O)NC(CC1=CC=CC=C1)C(=O)NC(CC2=CC=C(C=C2)NS(=O)(=O)O)C3=CSC(=N3)C4=CC=CS4

2.1.5 Isomeric SMILES

COC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC2=CC=C(C=C2)NS(=O)(=O)O)C3=CSC(=N3)C4=CC=CS4

2.2 Other Identifiers

2.2.1 UNII

0WAX4UT396

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Akb-9778

2.3.2 Depositor-Supplied Synonyms

1. 1008510-37-9

2. Akb-9778

3. Razuprotafib [inn]

4. Razuprotafib [usan]

5. 0wax4ut396

6. Razuprotafib (usan)

7. [4-[(2s)-2-[[(2s)-2-(methoxycarbonylamino)-3-phenylpropanoyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic Acid

8. Carbamic Acid, N-((1s)-2-oxo-1-(phenylmethyl)-2-(((1s)-2-(4-(sulfoamino)phenyl)-1-(2-(2-thienyl)-4-thiazolyl)ethyl)amino)ethyl)-, C-methyl Ester

9. N-(4-{(2s)-2-{(2s)-2-[(methoxycarbonyl)amino]-3-phenylpropanamido}-2-[2-(thiophen-2-yl)-1,3-thiazol-4-yl]ethyl}phenyl)sulfamic Acid

10. Razuprotafib [usan:inn]

11. Unii-0wax4ut396

12. Razuprotafib [who-dd]

13. Schembl679459

14. Chembl3931971

15. Gtpl11336

16. Akb9778

17. Bdbm359124

18. Us10220048, Compound Aa34

19. Who 10271

20. Compound Aa34 [us10220048]

21. At18581

22. Hy-109041

23. Cs-0031483

24. D11540

25. N-(4-((2s)-2-((2s)-2-((methoxycarbonyl)amino)- 3-phenylpropanamido)-2-(2-(thiophen-2-yl)-1,3-thiazol4-yl)ethyl)phenyl)sulfamic Acid

2.4 Create Date

2010-07-26

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₆N₄O₆S₃
Molecular Weight	586.7 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	586.10144808 g/mol
Monoisotopic Mass	586.10144808 g/mol
Topological Polar Surface Area	212 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	906
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Mechanism of Action

Razuprotafib inhibits [VE-PTP](https://go.drugbank.com/bio_entities/BE0003769) (a negative regulator of Tie2 in diseased blood vessels) by binding and inhibiting the intracellular catalytic domain of VE-PTP that inactivates Tie2. This in turn allows razuprotafib to restore Tie2 activation to allow for enhancement of endothelial function and stabilization of blood vessels. Razuprotafib is being investigated against diabetic vascular complications and acute respiratory distress syndrome (ARDS) in COVID-19.