リファペンチン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/11/14 11:30:26」(JST)
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Rifapentine
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Systematic (IUPAC) name |
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z,26E)-26-{[(4-cyclopentylpiperazin-1-yl)amino]methylidene}-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27-trioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl acetate |
Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a602026 |
Pregnancy cat. |
? |
Legal status |
? |
Pharmacokinetic data |
Bioavailability |
increases when administered with food |
Identifiers |
CAS number |
61379-65-5 Y |
ATC code |
J04AB05 |
PubChem |
CID 5462354 |
DrugBank |
DB01201 |
ChemSpider |
10482075 Y |
UNII |
XJM390A33U Y |
KEGG |
D00879 Y |
ChEBI |
CHEBI:45304 Y |
ChEMBL |
CHEMBL1660 Y |
NIAID ChemDB |
007686 |
Synonyms |
3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin |
Chemical data |
Formula |
C47H64N4O12 |
Mol. mass |
877.031 g/mol |
SMILES
- CC(=O)O[C@H]3[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc6c(/C=N/N1CCN(CC1)C2CCCC2)c(O)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O
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InChI
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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 Y
Key:WDZCUPBHRAEYDL-GZAUEHORSA-N Y
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Y (what is this?) (verify)
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Rifapentine (INN, marketed under the brand name Priftin by Sanofi-Aventis) is an antibiotic drug used in the treatment of tuberculosis.
History
Rifapentine was first synthesized in 1965 by the same company that produced rifampin. The drug was approved by the Food and Drug Administration (FDA) in June 1998. It is synthesized in one step from rifampicine.
External links
- Rosenthal IM, Zhang M, Williams KN et al. (December 2007). "Daily Dosing of Rifapentine Cures Tuberculosis in Three Months or Less in the Murine Model". PLoS Medicine 4 (12): e344. doi:10.1371/journal.pmed.0040344. PMC 2140085. PMID 18092886. //www.ncbi.nlm.nih.gov/pmc/articles/PMC2140085/.
- Rifapentine bound to proteins in the PDB
Antimycobacterials, including tuberculosis treatment and leprostatic agents (J04)
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Nucleic acid inhibitor |
Rifamycins/
RNA polymerase inhibitor
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- Rifampicin#
- Rifabutin
- Rifapentine
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Antifolates/DSI
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- Dapsone#
- Acedapsone
- Aldesulfone sodium
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ASA
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- 4-Aminosalicylic acid# (Calcium aminosalicylate
- Sodium aminosalicylate)
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Protein synthesis inhibitor |
Aminoglycosides
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- Amikacin#
- Capreomycin#
- Kanamycin#
- Streptomycin#
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Oxazolidone
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Cell envelope antibiotic |
Peptidoglycan layer
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- Alanine analogue: Cycloserine#
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Arabinogalactan layer
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- Ethylenediamine/arabinosyltransferase inhibitor: Ethambutol#
SQ109 †
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Mycolic acid layer
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- Hydrazides/mycolic acid synth. inhibition: Isoniazid#
- Thiocarbamides: Ethionamide#
- Prothionamide
- Thiocarlide
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Other/unknown |
- phenazine (Clofazimine)#
- pyrazine (Pyrazinamide#, Morinamide)
- isoxazole (Terizidone)
- Bedaquiline†
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Combinations |
- Rifampicin/isoniazid/pyrazinamide
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
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Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Trimethoprim#
- Brodimoprim
- Tetroxoprim
- Iclaprim†
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Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
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Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
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Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
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Other/ungrouped |
- sulfanilamide
- Sulfacetamide
- Sulfametrole
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Combinations |
- Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine
- Nalidixic acid
- Oxolinic acid
- Pipemidic acid
- Piromidic acid
- Rosoxacin
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Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
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3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
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4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
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Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
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Related (DG) |
- Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
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Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
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RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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UpToDate Contents
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English Journal
- Preliminary pharmacokinetic study of repeated doses of rifampin and rifapentine in Guinea pigs.
- Dutta NK, Alsultan A, Peloquin CA, Karakousis PC.SourceCenter for Tuberculosis Research, Johns Hopkins University School of Medicine, Baltimore, Maryland, USA.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2013 Mar;57(3):1535-7. doi: 10.1128/AAC.01933-12. Epub 2013 Jan 7.
- Substitution of rifapentine (RFP) for rifampin (RIF) in the standard antituberculous regimen reduces the time required to cure chronic tuberculosis (TB) infection in mice, but not in guinea pigs. In order to gain insight into these discrepant findings, we conducted a steady-state pharmacokinetic (PK
- PMID 23295923
- Improving existing tools for Mycobacterium xenopi treatment: assessment of drug combinations and characterization of mouse models of infection and chemotherapy.
- Andréjak C, Almeida DV, Tyagi S, Converse PJ, Ammerman NC, Grosset JH.SourceJohns Hopkins University School of Medicine, Center for Tuberculosis Research, 1550 Orleans Street, Baltimore, MD 21231, USA.
- The Journal of antimicrobial chemotherapy.J Antimicrob Chemother.2013 Mar;68(3):659-65. doi: 10.1093/jac/dks421. Epub 2012 Nov 5.
- BACKGROUND: Mycobacterium xenopi is a common agent of non-tuberculous mycobacterial lung diseases in Europe. However, an optimal treatment regimen for M. xenopi infection has not yet been established. Appropriate in vitro and in vivo model systems are needed for characterization of the activity of p
- PMID 23129730
- Rilpivirine: a new non-nucleoside reverse transcriptase inhibitor.
- Sharma M, Saravolatz LD.SourceDivision of Infectious Disease, Department of Medicine, St John Hospital & Medical Center, Detroit, MI, USA. mamta.sharma@stjohn.org
- The Journal of antimicrobial chemotherapy.J Antimicrob Chemother.2013 Feb;68(2):250-6. doi: 10.1093/jac/dks404. Epub 2012 Oct 25.
- Rilpivirine is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) that is approved for HIV-1 treatment-naive adult patients in combination with other antiretroviral agents. The recommended dose is a 25 mg tablet once daily taken orally with a meal. Due to cytochrome P450 3A4 enzyme inducti
- PMID 23099850
Japanese Journal
- 第77回総会特別講演 : 新しい抗結核薬開発の展望
- 冨岡 治明
- 結核 77(8), 573-584, 2002-08-15
- … First, I briefly reviewed some new findings (mainly reported after 2000) on the pharmacological status of rifamycin derivatives (rifabutin, rifapentine, and rifalazil), fluoroquinolones (cipro-floxacin, ofloxacin, sparfloxacin, levofloxacin, gatifloxacin, sitafloxacin, moxifloxacin, and others), and new macrolides (clarithromycin, azithromycin, and roxithromycin).<BR>Second, I decribed other types of agents which are being developed as antimycobacterial drugs. …
- NAID 130001428775
- Rifapentine and isoniazid once a week versus rifampicin and isoniazid twice a week for treatment of drug-susceptible pulmonary tuberculosis in HIV-negative patients : a randomized clinical trial
- Effectiveness of once-weekly rifapentine and moxifloxacin regimens against Mycobacterium tuberculosis in mice
Related Links
- Risk of relapse was higher in the rifapentine regimen. During the Intensive Phase of treatment the rate of noncompliance with companion medications was somewhat higher for the rifapentine regimen than for the rifampin regimen. Most ...
- rifapentine /rif·a·pen·tine/ (-pen?tēn) a synthetic rifamycin antibiotic used in the treatment of pulmonary tuberculosis. rifapentine, an antitubercular. indications Rifapentine is used to treat pulmonary tuberculosis. It must be used in ...
Related Pictures
★リンクテーブル★
[★]
- 英
- rifamycin
- ラ
- rifamycinum
- 関
- rifabutin rifampin rifapentine
- リファマイシン系抗菌薬