User:Mr. Ibrahem/Rifaximin

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Mr. Ibrahem/Rifaximin
Clinical data
Trade namesXifaxan, Xifaxanta, Normix, others
AHFS/Drugs.comMonograph
MedlinePlusa604027
Routes of
administration
By mouth
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability< 0.4%
MetabolismLiver
Elimination half-life6 hours
ExcretionFecal (97%)
Identifiers
  • (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26S,27S,28E)-5,6,21,23,25-pentahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca-[1,11,13]trienimino)benzofuro
    [4,5-e]pyrido[1,2-a]-benzimida-zole-1,15(2H)-dione,25-acetate
Chemical and physical data
FormulaC43H51N3O11
Molar mass785.891 g·mol−1
3D model (JSmol)
  • 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)Nc6c2c(nc1cc(C)ccn12)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O
  • InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1 checkY
  • Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rifaximin, sold under the trade name Xifaxan among others, is an antibiotic used to treat hepatic encephalopathy, irritable bowel syndrome, and traveler's diarrhea.[1] Specifically it can be used to decrease the number of episodes of hepatic encephalopathy.[2] It is not effective for a number of types of diarrhea including Salmonella.[1] It is taken by mouth.[2]

Common side effects include nausea, headache, and abdominal discomfort.[1] Other side effects may include joint pain, mood changes, swelling, skin rash, and Clostridium difficile colitis.[2][1] Use in pregnancy is not recommended while use during breastfeeding is believed to be safe for the baby.[2] It is in the rifamycin family of medications.[2]

Rifaximin was approved for medical use in the United States in 2004.[1] In United States the dose for hepatic encephalopathy costs $1,864 per month as of January 2017.[3] In the UK, 56 tablets of the 550mg dose costs the NHS around 260 pounds as of 2020.[2] As of 2020 no generic version is available in the United States.[4]

References[edit]

  1. ^ a b c d e f g "Rifaximin". The American Society of Health-System Pharmacists. Archived from the original on 25 June 2012. Retrieved 8 January 2017.
  2. ^ a b c d e f BNF (80 ed.). London: BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 609. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
  3. ^ "NADAC as of 2017-01-25". Centers for Medicare and Medicaid Services. Archived from the original on 2017-02-02. Retrieved 25 January 2017.
  4. ^ "Generic Xifaxan Availability". Drugs.com. Archived from the original on 5 June 2016. Retrieved 8 October 2020.