motixafortide   Click here for help

GtoPdb Ligand ID: 10679

Synonyms: 4F-Benzoyl-TN14003 | Aphexda® | BKT140 | BL-8040 | TF14016 [4]
Approved drug Immunopharmacology Ligand
motixafortide is an approved drug (FDA (2023))
Compound class: Peptide or derivative
Comment: Motixafortide (BL8040) is a CXCR4 antagonist that is being developed by Biokine Therapeutics [1]. It is a 14-residue polypeptide modified from a naturally occurring horseshoe crab protein. Motixafortide acts as an inverse agonist in [35S]GTPγS binding assays [1]. It induces safe and efficient stem cell mobilisation in MM patients in preparation for autologous stem cell transplantation [3], and it is being proposed as a mechanism to improve anti-tumour immune reponse against solid tumours [2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCCC[C@@H]1NC(=O)[C@H](CCCNC(=O)N)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)CCCCN)CCC2)Cc1ccc(cc1)O)CCCNC(=N)N)CCCNC(=O)N)C(=O)N[C@H](C(=O)N)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1ccc(cc1)F)CCCNC(=N)N)CCCNC(=N)N)Cc1ccc2c(c1)cccc2
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H](CCCNC(=O)N)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)CCCCN)CCC2)Cc1ccc(cc1)O)CCCNC(=N)N)CCCNC(=O)N)C(=O)N[C@H](C(=O)N)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1ccc(cc1)F)CCCNC(=N)N)CCCNC(=N)N)Cc1ccc2c(c1)cccc2
InChI InChI=1S/C97H144FN33O19S2/c98-60-33-31-58(32-34-60)78(135)119-65(19-8-42-113-93(104)105)79(136)121-68(21-10-44-115-95(108)109)83(140)126-73(51-56-25-30-57-14-1-2-15-59(57)48-56)87(144)130-75-53-152-151-52-74(88(145)118-63(77(101)134)18-7-41-112-92(102)103)129-84(141)69(23-12-46-117-97(111)150)122-81(138)66(20-9-43-114-94(106)107)124-86(143)72(50-55-28-37-62(133)38-29-55)128-90(147)76-24-13-47-131(76)91(148)70(17-4-6-40-100)125-82(139)64(16-3-5-39-99)120-80(137)67(22-11-45-116-96(110)149)123-85(142)71(127-89(75)146)49-54-26-35-61(132)36-27-54/h1-2,14-15,25-38,48,63-76,132-133H,3-13,16-24,39-47,49-53,99-100H2,(H2,101,134)(H,118,145)(H,119,135)(H,120,137)(H,121,136)(H,122,138)(H,123,142)(H,124,143)(H,125,139)(H,126,140)(H,127,146)(H,128,147)(H,129,141)(H,130,144)(H4,102,103,112)(H4,104,105,113)(H4,106,107,114)(H4,108,109,115)(H3,110,116,149)(H3,111,117,150)/t63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-/m0/s1
InChI Key JJVZSYKFCOBILL-MKMRYRNGSA-N
References
1. Beider K, Begin M, Abraham M, Wald H, Weiss ID, Wald O, Pikarsky E, Zeira E, Eizenberg O, Galun E et al.. (2011)
CXCR4 antagonist 4F-benzoyl-TN14003 inhibits leukemia and multiple myeloma tumor growth.
Exp Hematol, 39 (3): 282-92. [PMID:21138752]
2. Fahham D, Weiss ID, Abraham M, Beider K, Hanna W, Shlomai Z, Eizenberg O, Zamir G, Izhar U, Shapira OM et al.. (2012)
In vitro and in vivo therapeutic efficacy of CXCR4 antagonist BKT140 against human non-small cell lung cancer.
J Thorac Cardiovasc Surg, 144 (5): 1167-1175.e1. [PMID:22925564]
3. Peled A, Abraham M, Avivi I, Rowe JM, Beider K, Wald H, Tiomkin L, Ribakovsky L, Riback Y, Ramati Y et al.. (2014)
The high-affinity CXCR4 antagonist BKT140 is safe and induces a robust mobilization of human CD34+ cells in patients with multiple myeloma.
Clin Cancer Res, 20 (2): 469-79. [PMID:24246358]
4. Tamamura H, Hiramatsu K, Mizumoto M, Ueda S, Kusano S, Terakubo S, Akamatsu M, Yamamoto N, Trent JO, Wang Z et al.. (2003)
Enhancement of the T140-based pharmacophores leads to the development of more potent and bio-stable CXCR4 antagonists.
Org Biomol Chem, 1 (21): 3663-9. [PMID:14649897]