RIVIPANSEL SODIUM

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C58H70N6O31S3.4Na
Molecular Weight	1535.352
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].[Na+].[Na+].C[C@@H]1O[C@@H](O[C@@H]2[C@H](C[C@H](C[C@H]2O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H](CC4CCCCC4)C([O-])=O)[C@H]3OC(=O)C5=CC=CC=C5)C(=O)NCCNC(=O)COCCOCC(=O)NC6=CC(=CC7=CC(=CC(=C67)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)NC(=O)C8=CC(=O)NC(=O)N8)[C@@H](O)[C@H](O)[C@@H]1O

InChI

InChIKey=QQDCIMVGFXSAJH-DJFGCAFRSA-J

InChI=1S/C58H74N6O31S3.4Na/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);;;;/q;4*+1/p-4/t27-,31+,35-,37+,38-,39+,45+,46-,47+,48-,49+,50-,51+,56-,57+;;;;/m0..../s1

HIDE SMILES / InChI

Description
Sources: http://www.bloodjournal.org/content/128/22/270 | https://www.ncbi.nlm.nih.gov/pubmed/25733584 | https://www.drugbank.ca/salts/DBSALT002408 | http://glycomimetics.com/pipeline/programs/rivipansel-gmi-1070/ | https://clinicaltrials.gov/ct2/show/NCT02187003 | https://clinicaltrials.gov/ct2/show/NCT02433158

Rivipansel (GMI-1070) is a glycomimetic compound that acts as a pan-selectin inhibitor (binding to E-, P- and L-selectin). It has a 100-fold greater inhibitory acitivity for E-selectin than for P-selectin. In a phase II clinical trial, rivipansel has shown potential to reduce time of resolution for vaso-occlusive crises (although statistically insignificant) and to reduce opioid analgesic use in sickle cell disease patients. Two phase III studies evaluating the efficacy and safety of rivipansel in sickle cell disease patients were still ongoing in 2019. Besides studies in sickle cell disease or related disorders, clinical trials have also evaluated the use of rivipansel in moderate hepatic and renal impairment.

Originator

Approval Year

PubMed

Title	Date	PubMed
GMI-1070, a novel pan-selectin antagonist, reverses acute vascular occlusions in sickle cell mice.	2010-09-09	20508165
Primary role for adherent leukocytes in sickle cell vascular occlusion: a new paradigm.	2002-03-05	11880644

Name

Type

Language

RIVIPANSEL SODIUM

Official Name

English

GMI-1070

Preferred Name

English

PF-06460031-02

Code

English

RIVIPANSEL SODIUM [USAN]

Common Name

English

PF-0646003102

Code

English

Rivipansel sodium [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C26170