(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate

• ChemBase ID: 1071
• Molecular Formular: C47H64N4O12
• Molecular Mass: 877.03066
• Monoisotopic Mass: 876.45207351
• SMILES: c12c3c4C(=O)[C@@](O/C=C/[C@@H]([C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H](O)[C@H](/C=C/C=C(\C(=O)Nc(c2O)c(c3O)/C=N/N2CCN(CC2)C2CCCC2)/C)C)C)O)C)OC(=O)C)C)OC)(Oc4c(c1O)C)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C4CCCC4)c(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@H]1C)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
• InChIKey: WDZCUPBHRAEYDL-GZAUEHORSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate; (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• IUPAC Traditional name: @rifapentine
• Brand Name: Priftin
• Synonyms: Cyclopentyl rifampin; Rifapentine; Priftin; Cyclopentylrifampicin

Database IDs

• CAS Number: 61379-65-5
• PubChem SID: 46507322; 160964534
• PubChem CID: 6323497

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.0085845
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 2.4104726
• LogD (pH = 7.4): 3.6600382
• Log P: 3.5568845
• Molar Refractivity: 241.996 cm^3
• Polarizability: 93.10482 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.83
• LOG S: -4.61
• Solubility (Water): 2.13e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01201

• Drug Groups: approved
• Description: Rifapentine is an antibiotic drug used in the treatment of tuberculosis. It inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.
• Indication: For the treatment of pulmonary tuberculosis.
• Pharmacology: Rifapentine is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifampin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency.
• Affected Organisms: Mycobacterium
• Biotransformation: Hepatic
• Absorption: Rapidly and well absorbed from the gastrointestinal tract.
• Protein Binding: 97.7% (bound to plasma proteins)
• Elimination: Following a single 600 mg oral dose of radiolabeled rifapentine to healthy volunteers (n=4), 87% of the total 14C rifapentine was recovered in the urine (17%) and feces (70%).
• Distribution: * 70.2 ± 9.1 L
• Clearance: * Apparent Oral cl=2.51 +/- 0.14 L/h [Male tuberculosis patients who received 600 mg rifapentine in combination with isoniazid, pyrazinamide and ethambutol]; * Apparent Oral cl=1.69 +/- 0.41 L/h [Female tuberculosis patients who received 600 mg rifapentine in combination with isoniazid, pyrazinamide and ethambutol]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1760

Research Area: Infection
Biological Activity:
Rifapentine (Priftin) is an antibiotic compound used in the treatment of tuberculosis. Treatment begins in an intensive phase of twice-weekly dosing, followed by a maintenance phase of once-weekly dosing. Rifapentine (Priftin) is an antibiotic that kills the bacterium that causes tuberculosis, Mycobacterium tuberculosis. Rifapentine (Priftin) targets DNA-dependent RNA polymerase — proteins that are necessary for RNA synthesis and the production of proteins. This process is different in human (eukaryotic) cells and bacteria; rifamycins, like rifapentine, only affects this process in bacteria. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Rifapentine