Uproleselan

Synopsis, Chemistry

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Also known as: Uproleselan [usan], Gmi-1271, Gmi-1271 free acid, Pe952anf83, 1983970-12-2, Uproleselan [inn]

Molecular Formula

C₆₀H₁₀₉N₃O₂₇

Molecular Weight

1304.5 g/mol

InChI Key

LYSYOXNOOPBOSC-NGSKMYNLSA-N

FDA UNII

PE952ANF83

Uproleselan is a synthetic, glycomimetic molecule and E-selectin (CD62E) antagonist, with potential anti-thrombotic, antineoplastic and chemopotentiating activities. Upon administration, uproleselan binds to E-selectin expressed on endothelial cells and prevents their interaction with selectin-E ligand-expressing cancer cells. This may prevent tumor cell activation, migration and metastasis. GMI-1271 also interferes with the binding of selectin E-expressing vascular endothelial cells to selectin-E ligand-expressing monocytes and neutrophils, thereby disrupting their activation. Consequently, this inhibits both the activation of the coagulation cascade and thrombus formation. This agent also prevents both leukocyte activation and inflammation. E-selectin is a cell adhesion molecule involved in cell rolling, signaling and chemotaxis; it also plays a crucial role in inflammatory processes and cancer.

1 2D Structure

Uproleselan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[(2R,3R,4R,5R,6R)-3-acetamido-2-[(1R,2R,3S,5R)-3-ethyl-5-[2-[3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethylcarbamoyl]-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxycyclohexyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-cyclohexylpropanoic acid

2.1.2 InChI

InChI=1S/C60H109N3O27/c1-5-44-38-45(39-46(55(44)90-60-54(70)53(69)51(67)41(2)86-60)88-59-50(63-42(3)65)56(52(68)48(40-64)89-59)87-47(58(72)73)37-43-9-7-6-8-10-43)57(71)62-13-12-61-49(66)11-14-75-17-18-77-21-22-79-25-26-81-29-30-83-33-34-85-36-35-84-32-31-82-28-27-80-24-23-78-20-19-76-16-15-74-4/h41,43-48,50-56,59-60,64,67-70H,5-40H2,1-4H3,(H,61,66)(H,62,71)(H,63,65)(H,72,73)/t41-,44-,45+,46+,47-,48+,50+,51+,52-,53+,54-,55+,56+,59+,60-/m0/s1

2.1.3 InChI Key

LYSYOXNOOPBOSC-NGSKMYNLSA-N

2.1.4 Canonical SMILES

CCC1CC(CC(C1OC2C(C(C(C(O2)C)O)O)O)OC3C(C(C(C(O3)CO)O)OC(CC4CCCCC4)C(=O)O)NC(=O)C)C(=O)NCCNC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOC

2.1.5 Isomeric SMILES

CC[C@H]1C[C@H](C[C@H]([C@@H]1O[C@H]2[C@H]([C@@H]([C@@H]([C@@H](O2)C)O)O)O)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O[C@@H](CC4CCCCC4)C(=O)O)NC(=O)C)C(=O)NCCNC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOC

2.2 Other Identifiers

2.2.1 UNII

PE952ANF83

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy)-3-cyc

2. Abi-701

3. Abi701

4. Gmi-1271

5. Gmi-1271 Free Acid

6. Gmi-1271 Sodium

7. Gmi-1687

8. Sodium (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy

9. Uproleselan Sodium

2.3.2 Depositor-Supplied Synonyms

1. Uproleselan [usan]

2. Gmi-1271

3. Gmi-1271 Free Acid

4. Pe952anf83

5. 1983970-12-2

6. Uproleselan [inn]

7. Uproleselan (usan/inn)

8. Unii-pe952anf83

9. Uproleselan [who-dd]

10. Chembl3989971

11. Gtpl11995

12. Gmi1271

13. Db14829

14. D11332

15. (2s)-2-(((2r,3r,4r,5r,6r)-3-acetamido-2-(((1r,2r,3s,5r)-5-((2-(4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamido)ethyl)carbamoyl)-3-ethyl-2-(alpha-l-galactopyranosyloxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy)-3-cyclohexylpropanoic Acid

16. 4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxaoctatriacontanamide, N-(2-((((1r,3r,4r,5s)-3-((2-(acetylamino)-3-o-((1s)-1-carboxy-2-cyclohexylethyl)-2-deoxy-bata-d-galactopyranosyl)oxy)-4-((6-deoxy-alpha-l-galactopyranosyl)oxy)-5-ethylcyclohexyl)carbonyl)amino)ethyl)-

2.4 Create Date

2013-07-15

3 Chemical and Physical Properties

Molecular Formula	C₆₀H₁₀₉N₃O₂₇
Molecular Weight	1304.5 g/mol
XLogP3	-2
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	27
Rotatable Bond Count	52
Exact Mass	1303.72484521 g/mol
Monoisotopic Mass	1303.72484521 g/mol
Topological Polar Surface Area	383 Å²
Heavy Atom Count	90
Formal Charge	0
Complexity	1870
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1