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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
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 Weight 1304.5 g/mol
Molecular Formula C60H109N3O27
XLogP3-2
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count27
Rotatable Bond Count52
Exact Mass1303.72484521 g/mol
Monoisotopic Mass1303.72484521 g/mol
Topological Polar Surface Area383 Ų
Heavy Atom Count90
Formal Charge0
Complexity1870
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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ABOUT THIS PAGE

Uproleselan Manufacturers

A Uproleselan manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Uproleselan, including repackagers and relabelers. The FDA regulates Uproleselan manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Uproleselan API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Uproleselan Suppliers

A Uproleselan supplier is an individual or a company that provides Uproleselan active pharmaceutical ingredient (API) or Uproleselan finished formulations upon request. The Uproleselan suppliers may include Uproleselan API manufacturers, exporters, distributors and traders.

Uproleselan GMP

Uproleselan Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Uproleselan GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Uproleselan GMP manufacturer or Uproleselan GMP API supplier for your needs.

Uproleselan CoA

A Uproleselan CoA (Certificate of Analysis) is a formal document that attests to Uproleselan's compliance with Uproleselan specifications and serves as a tool for batch-level quality control.

Uproleselan CoA mostly includes findings from lab analyses of a specific batch. For each Uproleselan CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Uproleselan may be tested according to a variety of international standards, such as European Pharmacopoeia (Uproleselan EP), Uproleselan JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Uproleselan USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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