Upamostat

Upamostat
Legal status
Legal status	Investigational new drug;
Identifiers
	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;
CAS Number	1191101-18-4 ;
PubChem CID	9852201;
DrugBank	DB13052;
ChemSpider	28189283;
UNII	S5M7KW6U17;
Chemical and physical data
Formula	C32H47N5O6S
Molar mass	629.82 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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; Key:HUASEDVYRABWCV-NDEPHWFRSA-N;

Upamostat (WX-671, Mesupron) is a drug which acts as an inhibitor of the serine protease enzyme urokinase. It is under development as a potential treatment agent for pancreatic cancer, acting to inhibit tumour metastasis.^[1]^[2]^[3]

References

^ Kuş C, Özer E, Korkmaz Y, Yurtcu E, Dağalp R (2018). "Benzamide and Benzamidine Compounds as New Inhibitors of Urokinasetype Plasminogen Activators". Mini Reviews in Medicinal Chemistry. 18 (20): 1753–1758. doi:10.2174/1389557518666180816110740. PMID 30112993. S2CID 52011447.
^ Heinemann V, Ebert MP, Laubender RP, Bevan P, Mala C, Boeck S (March 2013). "Phase II randomised proof-of-concept study of the urokinase inhibitor upamostat (WX-671) in combination with gemcitabine compared with gemcitabine alone in patients with non-resectable, locally advanced pancreatic cancer". British Journal of Cancer. 108 (4): 766–70. doi:10.1038/bjc.2013.62. PMC 3590684. PMID 23412098.
^ Froriep D, Clement B, Bittner F, Mendel RR, Reichmann D, Schmalix W, Havemeyer A (September 2013). "Activation of the anti-cancer agent upamostat by the mARC enzyme system". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 43 (9): 780–4. doi:10.3109/00498254.2013.767481. PMID 23379481. S2CID 20052617.

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Legal status

Legal status	Investigational new drug
Identifiers
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
CAS Number	1191101-18-4^Y
PubChem CID	9852201
DrugBank	DB13052
ChemSpider	28189283
UNII	S5M7KW6U17
Chemical and physical data
Formula	C₃₂H₄₇N₅O₆S
Molar mass	629.82 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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 Key:HUASEDVYRABWCV-NDEPHWFRSA-N