Structure via PubChem · Public domain (PubChem)
rifapentine
Sign in to saveAlso known as MDL-473, Priftin, Cyclopentylrifampicin, Priftin (tn), 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
Rifapentine, sold under the brand name Priftin, is an antibiotic used in the treatment of tuberculosis. In active tuberculosis it is used together with other antituberculosis medications. In latent tuberculosis it is typically used with isoniazid. It is taken by mouth.
Key facts
- Drug.verifiedrevid
- 464382415
- Drug.image
- Rifapentine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.tradename
- Priftin
- Drug.MedlinePlus
- a616011
- Drug.DailyMedID
- Rifapentine
- Drug.routes_of_administration
- By mouth
- Drug.class
- Macrolactam
- Drug.ATC_prefix
- J04
- Drug.ATC_suffix
- AB05
- Drug.legal_CA_comment
- Urgent Public Health Need
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- increases when administered with food
- Drug.CAS_number
- 61379-65-5
- Drug.PubChem
- 6323497
- Drug.PubChem2
- 135403821
- Drug.DrugBank
- DB01201
via Wikipedia infobox
Chemical data
- Formula
- C47H64N4O12
- Molecular weight
- 877 g/mol
- IUPAC name
- [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
- SMILES
- C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCN(CC5)C6CCCC6)/C
- InChIKey
- WDZCUPBHRAEYDL-GZAUEHORSA-N
- XLogP
- 6.7
- Polar surface area
- 220 Ų
- H-bond donors
- 6
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1998
- Admin. routes
- oral
- Indications
- pulmonary tuberculosis, osteomyelitis, HIV infection, tuberculosis
via ChEMBL · EBI
Research
885 papers- Four-Month Rifapentine Regimens with or without Moxifloxacin for Tuberculosis.The New England journal of medicine · 2021
- Rifapentine.2012
- Rifapentine.Drugs · 1998
- Rifapentine Population Pharmacokinetics and Dosing Recommendations for Latent Tuberculosis Infection.American journal of respiratory and critical care medicine · 2020
- Rifapentine.Tuberculosis (Edinburgh, Scotland) · 2008
via PubMed
Wikidata facts
- Subclass of
- rifamycin
- Mass
- 876.4521
- Has use
- medication
Show 6 more facts
- chemical formula
- C₄₇H₆₄N₄O₁₂
- medical condition treated
- pulmonary tuberculosis
- isomeric SMILES
- CC1=C(C2=C3C4=C1O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)NC(=C2O)C(=C3O)/C=N/N5CCN(CC5)C6CCCC6)/C)C)O)C)O)C)OC(=O)C)C)OC)C)O
- canonical SMILES
- CC1=C(C2=C3C4=C1OC(C4=O)(OC=CC(C(C(C(C(C(C(C(C=CC=C(C(=O)NC(=C2O)C(=C3O)C=NN5CCN(CC5)C6CCCC6)C)C)O)C)O)C)OC(=O)C)C)OC)C)O
- defined daily dose
- 0.11
- subject has role
- bactericide
via Wikidata · CC0
~7 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Adverse effects
- Pregnancy
- Contraindications
- Interactions
- Chemical structure
- History
- Society and culture
- Cancer-causing impurities
- References
- External links
{{Infobox drug | verifiedrevid = 464382415 | image = Rifapentine.svg | image_class = skin-invert-image | width = 250 | alt = | caption =
| pronounce = | tradename = Priftin | Drugs.com = | MedlinePlus = a616011 | DailyMedID = Rifapentine | pregnancy_AU = | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | class = Macrolactam | ATC_prefix = J04 | ATC_suffix = AB05 | ATC_supplemental =
Excerpted from Wikipedia’s “rifapentine” article, available under the CC BY-SA 4.0 licence.