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MedKoo Cat#: 461351 | Name: Rivipansel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rivipansel is a glycomimetic drug candidate that acts as a pan-selectin antagonist and reverses acute vascular occlusions in sickle cell mice.

Chemical Structure

Rivipansel
Rivipansel
CAS#927881-99-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 461351

Name: Rivipansel

CAS#: 927881-99-0 (free acid)

Chemical Formula: C58H74N6O31S3

Exact Mass: 1446.3561

Molecular Weight: 1447.42

Elemental Analysis: C, 48.13; H, 5.15; N, 5.81; O, 34.27; S, 6.64

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1189037-60-2 (sodium) 927881-99-0 (free acid)
Synonym
Rivipansel; GMI-1070; GMI 1070; GMI1070; PF-06460031; PF 06460031; PF06460031;
IUPAC/Chemical Name
(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-methyltetrahydro-2H-pyran-2-yl)oxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3-cyclohexylpropanoic acid
InChi Key
VXBNTHRZPJLRSS-PTCSXESPSA-N
InChi Code
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
SMILES Code
O=C(O)[C@@H](O[C@@H]1[C@@H](OC(C2=CC=CC=C2)=O)[C@H](O[C@H]3[C@H](O[C@H]4[C@@H](O)[C@H](O)[C@H](O)[C@H](C)O4)[C@@H](NC(C(NC5=O)=CC(N5)=O)=O)C[C@@H](C(NCCNC(COCCOCC(NC6=C7C(S(=O)(O)=O)=CC(S(=O)(O)=O)=CC7=CC(S(=O)(O)=O)=C6)=O)=O)=O)C3)O[C@H](CO)[C@@H]1O)CC8CCCCC8
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,447.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Telen MJ, Wun T, McCavit TL, De Castro LM, Krishnamurti L, Lanzkron S, Hsu LL, Smith WR, Rhee S, Magnani JL, Thackray H. Randomized phase 2 study of GMI-1070 in SCD: reduction in time to resolution of vaso-occlusive events and decreased opioid use. Blood. 2015 Apr 23;125(17):2656-64. doi: 10.1182/blood-2014-06-583351. Epub 2015 Mar 2. PubMed PMID: 25733584; PubMed Central PMCID: PMC4408290. 2: Okpala I. Investigational selectin-targeted therapy of sickle cell disease. Expert Opin Investig Drugs. 2015 Feb;24(2):229-38. doi: 10.1517/13543784.2015.963552. Epub 2014 Sep 22. Review. PubMed PMID: 25243412. 3: Kutlar A, Embury SH. Cellular adhesion and the endothelium: P-selectin. Hematol Oncol Clin North Am. 2014 Apr;28(2):323-39. doi: 10.1016/j.hoc.2013.11.007. Epub 2014 Jan 17. Review. PubMed PMID: 24589269. 4: Preston RC, Jakob RP, Binder FP, Sager CP, Ernst B, Maier T. E-selectin ligand complexes adopt an extended high-affinity conformation. J Mol Cell Biol. 2016 Feb;8(1):62-72. doi: 10.1093/jmcb/mjv046. Epub 2015 Jun 27. PubMed PMID: 26117840; PubMed Central PMCID: PMC4710209. 5: Field JJ. Can selectin and iNKT cell therapies meet the needs of people with sickle cell disease? Hematology Am Soc Hematol Educ Program. 2015;2015:426-32. doi: 10.1182/asheducation-2015.1.426. PubMed PMID: 26637753. 6: Telen MJ. Cellular adhesion and the endothelium: E-selectin, L-selectin, and pan-selectin inhibitors. Hematol Oncol Clin North Am. 2014 Apr;28(2):341-54. doi: 10.1016/j.hoc.2013.11.010. Epub 2014 Jan 17. Review. PubMed PMID: 24589270. 7: Wun T, Styles L, DeCastro L, Telen MJ, Kuypers F, Cheung A, Kramer W, Flanner H, Rhee S, Magnani JL, Thackray H. Phase 1 study of the E-selectin inhibitor GMI 1070 in patients with sickle cell anemia. PLoS One. 2014 Jul 2;9(7):e101301. doi: 10.1371/journal.pone.0101301. eCollection 2014. Erratum in: PLoS One. 2014;9(10):e111690. PubMed PMID: 24988449; PubMed Central PMCID: PMC4079300. 8: Chang J, Patton JT, Sarkar A, Ernst B, Magnani JL, Frenette PS. GMI-1070, a novel pan-selectin antagonist, reverses acute vascular occlusions in sickle cell mice. Blood. 2010 Sep 9;116(10):1779-86. doi: 10.1182/blood-2009-12-260513. Epub 2010 May 27. PubMed PMID: 20508165; PubMed Central PMCID: PMC2947397. 9: Tammara BK, Plotka A, Shafer FE, Readett DRJ, Riley S, Korth-Bradley JM. Lack of Effect of Rivipansel on QTc Interval in Healthy Adult African American Male Subjects. J Clin Pharmacol. 2017 Oct;57(10):1315-1321. doi: 10.1002/jcph.924. Epub 2017 May 16. PubMed PMID: 28510346. 10: Deal watch: Pfizer deal for selectin inhibitor highlights potential of glycomimetic drugs. Nat Rev Drug Discov. 2011 Dec 1;10(12):890. doi: 10.1038/nrd3622. PubMed PMID: 22129980. 11: Morikis VA, Chase S, Wun T, Chaikof EL, Magnani JL, Simon SI. Selectin catch-bonds mechanotransduce integrin activation and neutrophil arrest on inflamed endothelium under shear flow. Blood. 2017 Nov 9;130(19):2101-2110. doi: 10.1182/blood-2017-05-783027. Epub 2017 Aug 15. PubMed PMID: 28811304; PubMed Central PMCID: PMC5680610. 12: Azab AK, Quang P, Azab F, Pitsillides C, Thompson B, Chonghaile T, Patton JT, Maiso P, Monrose V, Sacco A, Ngo HT, Flores LM, Lin CP, Magnani JL, Kung AL, Letai A, Carrasco R, Roccaro AM, Ghobrial IM. P-selectin glycoprotein ligand regulates the interaction of multiple myeloma cells with the bone marrow microenvironment. Blood. 2012 Feb 9;119(6):1468-78. doi: 10.1182/blood-2011-07-368050. Epub 2011 Nov 16. PubMed PMID: 22096244; PubMed Central PMCID: PMC3286211. 13: Tammara BK, Harnisch LO. Dose Selection Based on Modeling and Simulation for Rivipansel in Pediatric Patients Aged 6 to 11 Years With Sickle Cell Disease. CPT Pharmacometrics Syst Pharmacol. 2017 Dec;6(12):845-854. doi: 10.1002/psp4.12263. Epub 2017 Dec 6. PubMed PMID: 29115052; PubMed Central PMCID: PMC5744176.

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BP Lipid 118

BP Lipid 118

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