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Also known as: 1051366-32-5, Pol6326, Cyclo(l-alanyl-l-cysteinyl-l-seryl-l-alanyl-d-prolyl-(2s)-2,4-diaminobutanoyl-l-arginyl-l-tyrosyl-l-cysteinyl-l-tyrosyl-l-glutaminyl-l-lysyl-d-prolyl-l-prolyl-l-tyrosyl-l-histidyl), cyclic (2->9)-disulfide, Balixafortide [inn], Balixafortide [usan], Balixafortide(pol6326)

Molecular Formula

C₈₄H₁₁₈N₂₄O₂₁S₂

Molecular Weight

1864.1 g/mol

InChI Key

OYWQJZAVFWOOBF-WBMPNIIXSA-N

Balixafortide is an orally bioavailable inhibitor of CXC chemokine receptor 4 (CXCR4) with receptor binding and hematopoietic stem cell-mobilization activities. Balixafortide binds to the chemokine receptor CXCR4, thereby preventing the binding of stromal derived factor-1 (SDF-1 or CXCL12) to the CXCR4 receptor and subsequent receptor activation. This may induce the mobilization of hematopoietic stem and progenitor cells from the bone marrow into blood. CXCR4, a chemokine receptor belonging to the G protein-coupled receptor (GPCR) gene family, plays an important role in chemotaxis and angiogenesis and is upregulated in several tumor cell types; CXCL12/CXCR4 interaction induces retention of hematopoietic cells in the bone marrow.

1 2D Structure

Balixafortide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(1R,4S,7S,10S,16S,22R,25S,28S,31S,34R,37S,40S,43S,46R,52S,55S)-25-(4-aminobutyl)-43-(2-aminoethyl)-40-(3-carbamimidamidopropyl)-55-(hydroxymethyl)-10,31,37-tris[(4-hydroxyphenyl)methyl]-7-(1H-imidazol-5-ylmethyl)-4,52-dimethyl-3,8,11,17,23,26,29,32,35,38,39,42,45,51,54,57-hexadecaoxo-59,60-dithia-2,5,6,9,12,18,24,27,30,33,36,41,44,50,53,56-hexadecazapentacyclo[32.23.4.012,16.018,22.046,50]henhexacontan-28-yl]propanamide

2.1.2 InChI

InChI=1S/C84H118N24O21S2/c1-44-70(116)102-62-41-130-131-42-63(77(123)98-57(35-46-14-20-50(110)21-15-46)69(115)68(114)53(10-5-31-91-84(88)89)94-73(119)56(28-30-86)97-79(125)64-11-6-32-106(64)81(127)45(2)93-76(122)61(40-109)101-78(62)124)103-74(120)58(36-47-16-22-51(111)23-17-47)99-72(118)55(26-27-67(87)113)95-71(117)54(9-3-4-29-85)96-80(126)65-12-7-33-107(65)83(129)66-13-8-34-108(66)82(128)60(37-48-18-24-52(112)25-19-48)100-75(121)59(105-104-44)38-49-39-90-43-92-49/h14-25,39,43-45,53-66,104-105,109-112H,3-13,26-38,40-42,85-86H2,1-2H3,(H2,87,113)(H,90,92)(H,93,122)(H,94,119)(H,95,117)(H,96,126)(H,97,125)(H,98,123)(H,99,118)(H,100,121)(H,101,124)(H,102,116)(H,103,120)(H4,88,89,91)/t44-,45-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64+,65+,66-/m0/s1

2.1.3 InChI Key

OYWQJZAVFWOOBF-WBMPNIIXSA-N

2.1.4 Canonical SMILES

CC1C(=O)NC2CSSCC(C(=O)NC(C(=O)C(=O)C(NC(=O)C(NC(=O)C3CCCN3C(=O)C(NC(=O)C(NC2=O)CO)C)CCN)CCCNC(=N)N)CC4=CC=C(C=C4)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C5CCCN5C(=O)C6CCCN6C(=O)C(NC(=O)C(NN1)CC7=CN=CN7)CC8=CC=C(C=C8)O)CCCCN)CCC(=O)N)CC9=CC=C(C=C9)O

2.1.5 Isomeric SMILES

C[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]3CCCN3C(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)C)CCN)CCCNC(=N)N)CC4=CC=C(C=C4)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]5CCCN5C(=O)[C@@H]6CCCN6C(=O)[C@@H](NC(=O)[C@@H](NN1)CC7=CN=CN7)CC8=CC=C(C=C8)O)CCCCN)CCC(=O)N)CC9=CC=C(C=C9)O

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 1051366-32-5

2. Pol6326

3. Cyclo(l-alanyl-l-cysteinyl-l-seryl-l-alanyl-d-prolyl-(2s)-2,4-diaminobutanoyl-l-arginyl-l-tyrosyl-l-cysteinyl-l-tyrosyl-l-glutaminyl-l-lysyl-d-prolyl-l-prolyl-l-tyrosyl-l-histidyl), Cyclic (2->9)-disulfide

4. Balixafortide [inn]

5. Balixafortide [usan]

6. Balixafortide(pol6326)

7. Balixafortide (pol6326)

8. Unii-prc974m49b

9. Prc974m49b

10. Gtpl11587

11. Pol 6326

12. Who 9915

13. S9725

14. Ala-cys-ser-ala-pro-arg-tyr-cys-tyr-gln-lys-pro-pro-tyr-his Cyclic (2->9)-disulfide

2.3 Create Date

2019-07-22

3 Chemical and Physical Properties

Molecular Formula	C₈₄H₁₁₈N₂₄O₂₁S₂
Molecular Weight	1864.1 g/mol
XLogP3	-3.5
Hydrogen Bond Donor Count	24
Hydrogen Bond Acceptor Count	29
Rotatable Bond Count	23
Exact Mass	1862.83447922 g/mol
Monoisotopic Mass	1862.83447922 g/mol
Topological Polar Surface Area	757 Å²
Heavy Atom Count	131
Formal Charge	0
Complexity	3970
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1