Mebendazole

Mebendazole
Clinical data
Trade namesVermox,[1] Ovex, others
Other namesMBZ
AHFS/Drugs.comMonograph
MedlinePlusa682315
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) / S5 and S6 for treatment of animals
  • CA: ℞-only / and OTC for treatment of animals[3]
  • UK: POM (Prescription only) / P[4]
  • US: ℞-only
Pharmacokinetic data
Bioavailability2–10%
Protein binding95%
MetabolismExtensive liver
Elimination half-life3–6 hours
ExcretionFeces, urine (5–10%)
Identifiers
IUPAC name
  • Methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.017
Chemical and physical data
FormulaC16H13N3O3
Molar mass295.298 g·mol−1
3D model (JSmol)
Melting point288.5 °C (551.3 °F)
SMILES
  • COC(=O)Nc3nc2ccc(C(=O)c1ccccc1)cc2[nH]3
InChI
  • InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21) Y
  • Key:OPXLLQIJSORQAM-UHFFFAOYSA-N Y
  (verify)

Mebendazole (MBZ), sold under the brand name Vermox among others, is a medication used to treat a number of parasitic worm infestations.[5] This includes ascariasis, pinworm infection, hookworm infections, guinea worm infections and hydatid disease, among others.[5] It has been used for treatment of giardiasis but is not a preferred agent.[6][7] It is taken by mouth.[5]

Mebendazole is usually well tolerated.[5] Common side effects include headache, vomiting, and ringing in the ears.[5] If used at large doses it may cause bone marrow suppression.[5] It is unclear if it is safe in pregnancy.[5][2] Mebendazole is a broad-spectrum antihelminthic agent of the benzimidazole type.[5]

Mebendazole came into use in 1971, after it was developed by Janssen Pharmaceutica in Belgium.[8] It is on the World Health Organization's List of Essential Medicines.[9] Mebendazole is available as a generic medication.[10]

  1. ^ Ebadi M (2008). Desk reference of clinical pharmacology (2nd ed.). Boca Raton: CRC Press. p. 403. ISBN 9781420047448. Archived from the original on 8 September 2017.
  2. ^ a b "Mebendazole Use During Pregnancy". Drugs.com. 29 July 2020. Archived from the original on 28 October 2020. Retrieved 30 September 2020.
  3. ^ "Vermox Product information". Health Canada. 25 April 2012. Archived from the original on 13 May 2021. Retrieved 12 June 2022.
  4. ^ "Mebendazole". Archived from the original on 23 October 2016. Retrieved 29 April 2016.
  5. ^ a b c d e f g h ASHP (3 June 2024). "Mebendazole". The American Society of Health-System Pharmacists. Archived from the original on 7 September 2015. Retrieved 12 December 2024.
  6. ^ ASHP. "Mebendazole". The American Society of Health-System Pharmacists. Archived from the original on 7 September 2015.
  7. ^ "Patient Care for Giardia Infection". Giardia. U.S. Centers for Disease Control and Prevention. 20 February 2024. Retrieved 12 December 2024.
  8. ^ Mehlhorn, Heinz (2001). Encyclopedic reference of parasitology. 107 tables (2 ed.). Berlin [u.a.]: Springer. p. 259. ISBN 9783540668299. Archived from the original on 8 September 2017.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ Hamilton, Richard J. (2012). Tarascon pocket pharmacopoeia (13 ed.). Burlington, Mass.: Jones & Bartlett Learning. p. 33. ISBN 9781449624286. Archived from the original on 8 September 2017.
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