Rivipansel

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Also known as: Gmi-1070, Pf-06460031, 927881-99-0, 4b115v09lb, (s)-2-(((2r,3r,4s,5s,6r)-3-(benzoyloxy)-2-(((1r,2r,3s,5r)-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-5-((2-(2-(2-(2-oxo-2-((3,6,8-trisulfonaphthalen-1-yl)amino)ethoxy)ethoxy)acetamido)ethyl)carbamoyl)-2-(((2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-, Rivipansel [usan]

Molecular Formula

C₅₈H₇₄N₆O₃₁S₃

Molecular Weight

1447.4 g/mol

InChI Key

VXBNTHRZPJLRSS-PTCSXESPSA-N

FDA UNII

4B115V09LB

Rivipansel is a synthetic, glycomimetic molecule and pan-selectin antagonist, with potential use in a vaso-occlusive crisis. Upon administration, rivipansel prevents the interaction between leukocytes and the endothelium and may prevent cell activation and adhesion. By preventing selectin-mediated cell adhesion in sickle cell anemia, this agent may inhibit red blood cell-white blood cell interactions, normalize blood flow and reduce inflammation and vascular occlusive pain. GMI-1070 has the strongest antagonistic activity towards E-selectin but a sulfate-binding domain allows for interactions with P- and L-selectins. Selectins, containing lectin- and EGF-like domains, are a family of cell adhesion molecules implicated in inflammatory processes and cancer.

1 2D Structure

Rivipansel

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[(2R,3R,4S,5S,6R)-3-benzoyloxy-2-[(1R,2R,3S,5R)-3-[(2,4-dioxo-1H-pyrimidine-6-carbonyl)amino]-5-[2-[[2-[2-[2-oxo-2-[(3,6,8-trisulfonaphthalen-1-yl)amino]ethoxy]ethoxy]acetyl]amino]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/C58H74N6O31S3/c1-27-45(69)47(71)48(72)56(90-27)95-49-35(62-53(74)36-23-41(66)64-58(78)63-36)19-31(20-37(49)92-57-51(94-55(77)29-10-6-3-7-11-29)50(46(70)39(24-65)93-57)91-38(54(75)76)16-28-8-4-2-5-9-28)52(73)60-13-12-59-42(67)25-88-14-15-89-26-43(68)61-34-21-32(96(79,80)81)17-30-18-33(97(82,83)84)22-40(44(30)34)98(85,86)87/h3,6-7,10-11,17-18,21-23,27-28,31,35,37-39,45-51,56-57,65,69-72H,2,4-5,8-9,12-16,19-20,24-26H2,1H3,(H,59,67)(H,60,73)(H,61,68)(H,62,74)(H,75,76)(H,79,80,81)(H,82,83,84)(H,85,86,87)(H2,63,64,66,78)/t27-,31+,35-,37+,38-,39+,45+,46-,47+,48-,49+,50-,51+,56-,57+/m0/s1

2.1.3 InChI Key

VXBNTHRZPJLRSS-PTCSXESPSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2C(CC(CC2OC3C(C(C(C(O3)CO)O)OC(CC4CCCCC4)C(=O)O)OC(=O)C5=CC=CC=C5)C(=O)NCCNC(=O)COCCOCC(=O)NC6=C7C(=CC(=C6)S(=O)(=O)O)C=C(C=C7S(=O)(=O)O)S(=O)(=O)O)NC(=O)C8=CC(=O)NC(=O)N8)O)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)O[C@@H]2[C@H](C[C@H](C[C@H]2O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O[C@@H](CC4CCCCC4)C(=O)O)OC(=O)C5=CC=CC=C5)C(=O)NCCNC(=O)COCCOCC(=O)NC6=C7C(=CC(=C6)S(=O)(=O)O)C=C(C=C7S(=O)(=O)O)S(=O)(=O)O)NC(=O)C8=CC(=O)NC(=O)N8)O)O)O

2.2 Other Identifiers

2.2.1 UNII

4B115V09LB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gmi-1070

2.3.2 Depositor-Supplied Synonyms

1. Gmi-1070

2. Pf-06460031

3. 927881-99-0

4. 4b115v09lb

5. (s)-2-(((2r,3r,4s,5s,6r)-3-(benzoyloxy)-2-(((1r,2r,3s,5r)-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-5-((2-(2-(2-(2-oxo-2-((3,6,8-trisulfonaphthalen-1-yl)amino)ethoxy)ethoxy)acetamido)ethyl)carbamoyl)-2-(((2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-

6. Rivipansel [usan]

7. 1189037-60-2

8. Rivipansel [usan:inn]

9. Unii-4b115v09lb

10. Starbld0029722

11. Rivipansel [inn]

12. Rivipansel (usan/inn)

13. Rivipansel [who-dd]

14. Gtpl8307

15. Chembl3707446

16. Schembl22657110

17. Db12778

18. D10487

19. Q27088557

20. (2s)-2-[(2r,3r,4s,5s,6r)-3-benzoyloxy-2-[(1r,2r,3s,5r)-3-[(2,4-dioxo-1h-pyrimidine-6-carbonyl)amino]-5-[2-[[2-[2-[2-oxo-2-[(3,6,8-trisulfonaphthalen-1-yl)amino]ethoxy]ethoxy]acetyl]amino]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

2.4 Create Date

2009-10-19

3 Chemical and Physical Properties

Molecular Formula	C₅₈H₇₄N₆O₃₁S₃
Molecular Weight	1447.4 g/mol
XLogP3	-2.6
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	31
Rotatable Bond Count	30
Exact Mass	1446.3560631 g/mol
Monoisotopic Mass	1446.3560631 g/mol
Topological Polar Surface Area	592 Å²
Heavy Atom Count	98
Formal Charge	0
Complexity	3190
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