Pixatimod

Synopsis, Chemistry

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Also known as: Pixatimod [inn], Pg-545 free acid, 66qr34c83n, 1144617-49-1, Pg545, Pixatimod [who-dd]

Molecular Formula

C₅₁H₈₈O₆₀S₁₃

Molecular Weight

2078.1 g/mol

InChI Key

LNUFLCYMSVYYNW-ZPJMAFJPSA-N

FDA UNII

66QR34C83N

Pixatimod is a synthetic sugar modified heparan sulfate mimetic and agonist of toll-like receptor 9 (TLR9), with potential immunostimulating, antineoplastic and anti-viral activities. Upon administration, pixatimod binds to and activates TLR9 expressed by dendritic cells (DCs) and B-cells. This initiates cytokine release from DCs and activates innate immune signaling pathways, and leads to the activation of natural killer (NK) cells to destroy tumor cells. The combination of pixatimod with certain checkpoint inhibitors may enhance the activation of cytotoxic T-lymphocytes to further kill tumor cells. In addition, pixatimod inhibits the cleavage of heparan sulfate from cell surface proteoglycan by heparanase (HPSE) and inhibits the infiltration of tumor-associated macrophages (TAMs). TLR9, a member of the TLR family, plays a fundamental role in pathogen recognition and activation of innate immunity.

1 2D Structure

Pixatimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3,5-disulfooxy-6-(sulfooxymethyl)oxan-4-yl] hydrogen sulfate

2.1.2 InChI

InChI=1S/C51H88O60S13/c1-22(2)7-6-8-23(3)27-11-12-28-26-10-9-24-17-25(13-15-50(24,4)29(26)14-16-51(27,28)5)95-46-42(108-121(79,80)81)38(104-117(67,68)69)34(30(96-46)18-91-112(52,53)54)100-47-43(109-122(82,83)84)39(105-118(70,71)72)35(31(97-47)19-92-113(55,56)57)101-48-44(110-123(85,86)87)40(106-119(73,74)75)36(32(98-48)20-93-114(58,59)60)102-49-45(111-124(88,89)90)41(107-120(76,77)78)37(103-116(64,65)66)33(99-49)21-94-115(61,62)63/h22-49H,6-21H2,1-5H3,(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63)(H,64,65,66)(H,67,68,69)(H,70,71,72)(H,73,74,75)(H,76,77,78)(H,79,80,81)(H,82,83,84)(H,85,86,87)(H,88,89,90)/t23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35-,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50+,51-/m1/s1

2.1.3 InChI Key

LNUFLCYMSVYYNW-ZPJMAFJPSA-N

2.1.4 Canonical SMILES

CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)OC5C(C(C(C(O5)COS(=O)(=O)O)OC6C(C(C(C(O6)COS(=O)(=O)O)OC7C(C(C(C(O7)COS(=O)(=O)O)OC8C(C(C(C(O8)COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C

2.1.5 Isomeric SMILES

C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COS(=O)(=O)O)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COS(=O)(=O)O)O[C@@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COS(=O)(=O)O)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)OS(=O)(=O)O)C)C

2.2 Other Identifiers

2.2.1 UNII

66QR34C83N

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Pixatimod [inn]

2. Pg-545 Free Acid

3. 66qr34c83n

4. 1144617-49-1

5. Pg545

6. Pixatimod [who-dd]

7. Unii-66qr34c83n

8. Gtpl9870

9. Chembl2078841

10. Compound 18 [pmid: 22458531]

2.4 Create Date

2012-08-06

3 Chemical and Physical Properties

Molecular Formula	C₅₁H₈₈O₆₀S₁₃
Molecular Weight	2078.1 g/mol
XLogP3	-4.2
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	60
Rotatable Bond Count	43
Exact Mass	2076.0204052 g/mol
Monoisotopic Mass	2076.0204052 g/mol
Topological Polar Surface Area	1010 Å²
Heavy Atom Count	124
Formal Charge	0
Complexity	5240
Isotope Atom Count	0
Defined Atom Stereocenter Count	29
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1