(6R,10R,11R,12Z,17Z,19Z,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone

• ChemBase ID: 1537
• Molecular Formular: C34H50N4O9S
• Molecular Mass: 690.8472
• Monoisotopic Mass: 690.3298502
• SMILES: S(=O)(=O)([C@H]1C2N(CC1)C(=O)c1nc(oc1)CC(=O)C[C@H](O)/C=C(\C=C/CNC(=O)/C=C\[C@H]([C@H](OC2=O)C(C)C)C)/C)CCN(CC)CC
• Canonical SMILES: CCN(CCS(=O)(=O)[C@@H]1CCN2C1C(=O)O[C@H](C(C)C)[C@H](C)/C=C\C(=O)NC/C=C\C(=C/[C@H](CC(=O)Cc1nc(C2=O)co1)O)\C)CC
• InChI: InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9-,12-11-,23-18-/t24-,25-,28-,31?,32-/m1/s1
• InChIKey: SUYRLXYYZQTJHF-FUODUHIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,10R,11R,12Z,17Z,19Z,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
• IUPAC Traditional name: (6R,10R,11R,12Z,17Z,19Z,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
• Synonyms: Dalfopristina [inn-spanish]; Dalfopristine [inn-french]; Dalfopristinum [inn-latin]; Dalfopristin

Database IDs

• CAS Number: 112362-50-2
• PubChem SID: 160964994; 46506561
• PubChem CID: 21943991

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.378627
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -0.012025763
• LogD (pH = 7.4): 1.4094774
• Log P: 1.581891
• Molar Refractivity: 182.8398 cm^3
• Polarizability: 70.6918 Å^3
• Polar Surface Area: 176.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.57
• LOG S: -3.98
• Solubility (Water): 7.16e-02 g/l

DETAILS

DrugBank - DB01764

• Drug Groups: approved
• Description: Dalfopristin is a combination of two antibiotics (Dalfopristin and quinupristin) used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. It is not effective against Enterococcus faecalis infections. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis.
• Indication: For the treatment of bacterial infections (usually in combination with quinupristin).
• Pharmacology: Dalfopristin is a streptogramin antibiotic, derived from pristinamycin IIA.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Converted to an active non-conjugated metabolite by hydrolysis.
• Half Life: The elimination half-life is approximately 0.70 hours.
• Protein Binding: Moderate
• References: Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. [Pubmed] ; Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97. [Pubmed] ; Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. [Pubmed] ; Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97. Pubmed
• Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. Pubmed
• Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. Pubmed
• Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. Pubmed