1-[3-(2-methanesulfonyl-10H-phenothiazin-10-yl)propyl]piperidine-4-carboxamide

• ChemBase ID: 174581
• Molecular Formular: C22H27N3O3S2
• Molecular Mass: 445.59808
• Monoisotopic Mass: 445.14938374
• SMILES: c1(ccc2c(c1)N(c1c(S2)cccc1)CCCN1CCC(CC1)C(=O)N)S(=O)(=O)C
• Canonical SMILES: NC(=O)C1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)S(=O)(=O)C
• InChI: InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)
• InChIKey: BQDBKDMTIJBJLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(2-methanesulfonyl-10H-phenothiazin-10-yl)propyl]piperidine-4-carboxamide
• IUPAC Traditional name: metopimazine
• Synonyms: 1-[3-[2-(Methylsulfonyl)-10H-phenothiazin-10-yl]propyl]-4-piperidinecarboxamide; 1-[3-[2-(Methylsulfonyl)phenothiazin-10-yl]propyl]isonipecotamide; 2-Methylsulfonyl-10-[3-(4-carbamoylpiperidino)propyl]phenothiazine; EXP 999; RP 9965; Vogalene; Metopimazine

Database IDs

• CAS Number: 14008-44-7
• PubChem SID: 164230491
• PubChem CID: 26388

CALCULATED PROPERTIES

• Acid pKa: 16.27108
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.2845952
• LogD (pH = 7.4): 1.8038454
• Log P: 2.0374322
• Molar Refractivity: 123.1592 cm^3
• Polarizability: 47.92647 Å^3
• Polar Surface Area: 83.71 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M338760

Metopimazine (MPZ) is used to prevent emesis during chemotherapies. Antiemetic.

REFERENCES

• Catz, P., et al.: Int. J. Pharm., 58, 93 (1990)
• Sato, K., et al.: J. Pharm. Sci., 80, 104 (1990)
• Herrstedt, J., et al.: Cancer Chemother. Pharmacol., 33, 53 (1990)
• Sigsgaard, T., et al.: J. Clin. Onc., 19, 2091 (1990)