RIVIPANSEL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C58H74N6O31S3
Molecular Weight	1447.425
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]8(O[C@@H]1[C@H](C[C@H](C[C@H]1O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O[C@@H](CC3CCCCC3)C(O)=O)[C@H]2OC(=O)C4=CC=CC=C4)C(=O)NCCNC(=O)COCCOCC(=O)NC5=CC(=CC6=CC(=CC(=C56)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)NC(=O)C7=CC(=O)NC(=O)N7)O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]8O

InChI

InChIKey=VXBNTHRZPJLRSS-PTCSXESPSA-N

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

HIDE SMILES / InChI

Molecular Formula	C58H74N6O31S3
Molecular Weight	1447.425
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Primary role for adherent leukocytes in sickle cell vascular occlusion: a new paradigm.	2002 Mar 5	11880644
GMI-1070, a novel pan-selectin antagonist, reverses acute vascular occlusions in sickle cell mice.	2010 Sep 9	20508165

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:57:14 GMT 2023` Edited by `admin` on `Sat Dec 16 07:57:14 GMT 2023`
Record UNII	4B115V09LB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIVIPANSEL

Official Name

English

rivipansel [INN]

Common Name

English

Rivipansel [WHO-DD]

Common Name

English

RIVIPANSEL [USAN]

Common Name

English

PF-06460031

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

274608