Balsalazide

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Balsalazide
Balsalazide structure.svg
Names
Trade namesColazide[1] Giazo, Colazal,[2]
  • (E)-5-([4-(2-carboxyethylcarbamoyl)phenyl]diazenyl)-2-hydroxybenzoic acid
Clinical data
Pregnancy
category
Routes of
use
By mouth
External links
AHFS/Drugs.comMonograph
US NLMBalsalazide
MedlinePlusa699052
Legal
License data
Legal status
Pharmacokinetics
Bioavailability<1%
Protein binding≥99%
Elimination half-life12hr
Chemical and physical data
FormulaC17H15N3O6
Molar mass357.322 g·mol−1
3D model (JSmol)
  • O=C(O)c1cc(ccc1O)/N=N/c2ccc(cc2)C(=O)NCCC(O)=O
  • InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+ checkY
  • Key:IPOKCKJONYRRHP-FMQUCBEESA-N checkY
 ☒NcheckY (what is this?)  (verify)

Balsalazide, sold under the brand name Colazide among others, is a medication used to treat ulcerative colitis.[1] It is usually for only a short duration of less than 12 weeks.[2] It is typically given by mouth as the disodium salt capsule.[1] It can be taken with or without food, and if unable to swallow the capsule, its contents can be sprinkled on a spoon of applesauce and taken immediately.[2]

An alternative may be required for people with asthma, kidney or liver problems.[1] Side effects include headache, feeling sick, stomach upset, diarrhea, joint pain, fever, sore throat, and runny nose.[2] Balsalazide may cause blood disorder, gallstones or lupus-like syndrome; which may cause tiredness, pale skin, feeling dizzy or short of breath.[1][2] Its effects in pregnancy are not known and it is generally not used in pregnancy.[2][4] Once taken by mouth, balsalazide passes unchanged through the stomach and small bowel, and releases mesalazine (5-ASA) when it reaches the large bowel, where ulcerative colitis affects.[5]

Balsalazide was first made in the 1980s and sold in the United Kingdom in 1996.[6] Colazal and Colazide are available as 750mg capsules for use in adults.[1][2] In the US, Colazal can be used in children over age 5-years, and Giazo is available as a 1.1g tablet for use in men over the age of 18 years, but for a maximum of eight weeks duration.[1][2] As of 2021, a months supply of the maintenance dose costs the NHS in the UK around £30.[1]

Medical use

Balsalazide is used to treat mild to moderate ulcerative colitis and to prevent acute attacks.[1]

Dose

An adult dose is typically 2.25g three times a day until symptoms settle, or for up to a maximum of 12 weeks.[1] Once settled, a maintenance dose is typically 1.5g twice a day, but can be more if required.[1] The maximum dose in adults is 6g in one day.[1] The Colazal form may be given to children over 5 years old.[2] A blood test to check for kidney problems is required before starting balsalazide.[4]

Availabilty

Colazal and Colazide are available as 750mg capsules.[1][2] The Giazo brand comes in a 1.1g tablet for use in men over the age of 18 years for a maximum of eight weeks duration.[2]

Side effects

An alternative may be required for people with asthma, kidney or liver problems.[1] Its effects in pregnancy are not known and it is generally not used in pregnancy.[2][4] Side effects include headache, feeling sick, stomach upset, diarrhea, joint pain, fever, sore throat, and runny nose.[2] Balsalazide may cause blood disorder, gallstones or lupus-like syndrome; which may cause tiredness, pale skin, feeling dizzy or short of breath.[1][2]

Mechanism

Balsalazide is a type of azo compound belonging to the aminosalicylates.[5] The mesalazine (5-ASA) in balsalazide is bound by an azo (N=N) bond to the inert (4-aminobenzoyl)-beta-alanine.[5] This azo-structure reduces absorption of balsalazide from the small intestine.[5] Once taken by mouth, balsalazide passes unchanged through the stomach and small bowel, but when it reaches azoreductase-producing bacteria in the large bowel, the azo bond is broken and 5-ASA is released at the site of the ulcerative colitis.[5] A dose of 6.75g of balsalazide is equivalent to 2.4g of mesalazine.[7] It is unclear how mesalazine works.[7]

Synthesis

Ex 3 is actually for Ipsalazide. See Ex 4 for Balsalazide proper. Same protocol but uses β-Alanine.

Balsalazide synthesis: Biorex Laboratories, GB 2080796  (1986).
  1. Starting material is 4-aminohippuric acid, obtained by coupling para-aminobenzoic acid and glycine.
  2. That product is then treated with nitrous acid to give the diazonium salt.
  3. Reaction of this species with salicylic acid proceeds at the position para to the phenol to give balsalazide.

History

Balsalazide was first produced in the 1980s by Biorex Laboratories and marketed as Colazal first in the UK in 1996.[6]

References

  1. 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 "1. Gastro-intestinal system". British National Formulary (BNF) (82 ed.). London: BMJ Group and the Pharmaceutical Press. September 2021 – March 2022. pp. 44–45. ISBN 978-0-85711-413-6.CS1 maint: date format (link)
  2. 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 2.12 2.13 "A - Z Drug List from Drugs.com: Balsalazide". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 November 2021.
  3. "Balsalazide Use During Pregnancy". Drugs.com. Retrieved 22 November 2021.
  4. 4.0 4.1 4.2 4.3 "Colazide 750mg Capsules - Summary of Product Characteristics (SmPC)". (emc). 3 January 2019. Retrieved 2 October 2020.
  5. 5.0 5.1 5.2 5.3 5.4 McQuaid, Kenneth R. (2020). "62. Drugs used in the treatment of gastrointestinal diseases". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. pp. 1150–1151. ISBN 978-1-260-45231-0.
  6. 6.0 6.1 Richmond, Lesley; Stevenson, Julie (2017). The Pharmaceutical Industry: A Guide to Historical Records. Routledge. p. 135. ISBN 978-1-351-88429-7.
  7. 7.0 7.1 Shargel, Leon; Kanfer, Isadore (2016). Generic Drug Product Development: Specialty Dosage Forms. CRC Press. ISBN 978-1-4200-2003-8.

External links

External sites:
Identifiers: