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Also known as: Pelcitoclax [inn], 317ubd60ml, 1619923-36-2, Unii-317ubd60ml, Pelcitoclax [who-dd], Chembl4802151

Molecular Formula

C₅₇H₆₆ClF₄N₆O₁₁PS₄

Molecular Weight

1281.9 g/mol

InChI Key

QIOCQCYXBYUYLH-YACUFSJGSA-N

FDA UNII

317UBD60ML

Pelcitoclax is a Bcl-2 homology (BH)-3 mimetic and selective inhibitor of the anti-apoptotic proteins B-cell lymphoma 2 (Bcl-2) and Bcl-XL, with potential pro-apoptotic and antineoplastic activities. Upon administration, pelcitoclax specifically binds to and inhibits the activity of the pro-survival proteins Bcl-2 and Bcl-XL. This restores apoptotic processes and inhibits cell proliferation in Bcl-2/Bcl-XL-dependent tumor cells. Bcl-2 and Bcl-XL, proteins belonging to the Bcl-2 family that are overexpressed in many cancers, play an important role in the negative regulation of apoptosis; tumor expression is associated with increased drug resistance and cancer cell survival.

1 2D Structure

Palcitoclax

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[1-[(3R)-3-[4-[[4-[4-[3-[2-(4-chlorophenyl)-5-methyl-4-methylsulfonyl-1-propan-2-ylpyrrol-3-yl]-5-fluorophenyl]piperazin-1-yl]phenyl]sulfamoyl]-2-(trifluoromethylsulfonyl)anilino]-4-phenylsulfanylbutyl]piperidine-4-carbonyl]oxypropylphosphonic acid

2.1.2 InChI

InChI=1S/C57H66ClF4N6O11PS4/c1-38(2)68-39(3)55(82(4,73)74)53(54(68)40-11-13-43(58)14-12-40)42-33-44(59)35-48(34-42)67-29-27-66(28-30-67)47-17-15-45(16-18-47)64-84(77,78)50-19-20-51(52(36-50)83(75,76)57(60,61)62)63-46(37-81-49-9-6-5-7-10-49)23-26-65-24-21-41(22-25-65)56(69)79-31-8-32-80(70,71)72/h5-7,9-20,33-36,38,41,46,63-64H,8,21-32,37H2,1-4H3,(H2,70,71,72)/t46-/m1/s1

2.1.3 InChI Key

QIOCQCYXBYUYLH-YACUFSJGSA-N

2.1.4 Canonical SMILES

CC1=C(C(=C(N1C(C)C)C2=CC=C(C=C2)Cl)C3=CC(=CC(=C3)F)N4CCN(CC4)C5=CC=C(C=C5)NS(=O)(=O)C6=CC(=C(C=C6)NC(CCN7CCC(CC7)C(=O)OCCCP(=O)(O)O)CSC8=CC=CC=C8)S(=O)(=O)C(F)(F)F)S(=O)(=O)C

2.1.5 Isomeric SMILES

CC1=C(C(=C(N1C(C)C)C2=CC=C(C=C2)Cl)C3=CC(=CC(=C3)F)N4CCN(CC4)C5=CC=C(C=C5)NS(=O)(=O)C6=CC(=C(C=C6)N[C@H](CCN7CCC(CC7)C(=O)OCCCP(=O)(O)O)CSC8=CC=CC=C8)S(=O)(=O)C(F)(F)F)S(=O)(=O)C

2.2 Other Identifiers

2.2.1 UNII

317UBD60ML

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(1-((3r)-3-(4-((4-(4-(3-(2-(4-chlorophenyl)-5-methyl-4-methylsulfonyl-1-propan-2-ylpyrrol-3-yl)-5-fluorophenyl)piperazin-1-yl)phenyl)sulfamoyl)-2-(trifluoromethylsulfonyl)anilino)-4-phenylsulfanylbutyl)piperidine-4-carbonyl)oxypropylphosphonic Acid

2. Apg 1252

3. Apg-1252

4. Apg1252

2.3.2 Depositor-Supplied Synonyms

1. Pelcitoclax [inn]

2. 317ubd60ml

3. 1619923-36-2

4. Unii-317ubd60ml

5. Pelcitoclax [who-dd]

6. Chembl4802151

7. Schembl15872908

8. Apg1252

9. Apg 1252 [who-dd]

10. Apg-1252

11. Nsc835773

12. Nsc-835773

13. Hy-109185

14. Cs-0116458

15. (r)-3-(1-(3-(4-(n-(4-(4-(3-(2-(4-chlorophenyl)-1-isopropyl-5-methyl-4-(methylsulfonyl)-1h-pyrrol-3-yl)-5-fluorophenyl)piperazin-1-yl)phenyl)sulfamoyl)-2-(trifluoromethylsulfonyl)phenylamino)-4-(phenylthio)butyl)piperidine-4-carbonyloxy)propylphosphonic Acid

16. 4-piperidinecarboxylic Acid, 1-((3r)-3-((4-(((4-(4-(3-(2-(4-chlorophenyl)-5-methyl-1-(1-methylethyl)-4-(methylsulfonyl)-1h-pyrrol-3-yl)-5-fluorophenyl)-1-piperazinyl)phenyl)amino)sulfonyl)-2-((trifluoromethyl)sulfonyl)phenyl)amino)-4-(phenylthio)butyl)-, 3-phosphonopropyl Ester

2.4 Create Date

2014-08-18

3 Chemical and Physical Properties

Molecular Formula	C₅₇H₆₆ClF₄N₆O₁₁PS₄
Molecular Weight	1281.9 g/mol
XLogP3	7.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	21
Rotatable Bond Count	24
Exact Mass	1280.3034690 g/mol
Monoisotopic Mass	1280.3034690 g/mol
Topological Polar Surface Area	275 Å²
Heavy Atom Count	84
Formal Charge	0
Complexity	2490
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1