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MedKoo Cat#: 146333 | Name: Acetylisoniazid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acetylisoniazid is a major metabolite of isoniazid, an antibiotic used in the treatment and prevention of tuberculosis. It is formed in the liver through acetylation by the enzyme N-acetyltransferase. While acetylisoniazid itself is not therapeutically active, its formation plays a key role in determining isoniazid's metabolism rate and potential toxicity, particularly in individuals who are slow or fast acetylators.

Chemical Structure

Acetylisoniazid
Acetylisoniazid
CAS#1078-38-2

Theoretical Analysis

MedKoo Cat#: 146333

Name: Acetylisoniazid

CAS#: 1078-38-2

Chemical Formula: C8H9N3O2

Exact Mass: 179.0695

Molecular Weight: 179.18

Elemental Analysis: C, 53.63; H, 5.06; N, 23.45; O, 17.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Acetylisoniazid;
IUPAC/Chemical Name
N'-acetylisonicotinohydrazide
InChi Key
CVBGNAKQQUWBQV-UHFFFAOYSA-N
InChi Code
1S/C8H9N3O2/c1-6(12)10-11-8(13)7-2-4-9-5-3-7/h2-5H,1H3,(H,10,12)(H,11,13)
SMILES Code
CC(=O)NNC(=O)C1=CC=NC=C1
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 179.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chen B, Shi HQ, Feng MR, Wang XH, Cao XM, Cai WM. Population Pharmacokinetics and Pharmacodynamics of Isoniazid and its Metabolite Acetylisoniazid in Chinese Population. Front Pharmacol. 2022 Jul 19;13:932686. doi: 10.3389/fphar.2022.932686. PMID: 35928262; PMCID: PMC9343941. 2: Amlabu V, Mulligan C, Jele N, Evans A, Gray D, Zar HJ, McIlleron H, Smith P. Isoniazid/acetylisoniazid urine concentrations: markers of adherence to isoniazid preventive therapy in children. Int J Tuberc Lung Dis. 2014 May;18(5):528-30. doi: 10.5588/ijtld.13.0730. PMID: 24903787; PMCID: PMC4229494. 3: Sharma S, Anand A, Verma N, Sharma V, Bhatia A, Patil AN, Banerjee D. Pharmacokinetic Assessment of Isoniazid and Acetylisoniazid in Carbon Tetrachloride-Induced Liver Injury Model in Wistar Rats. J Pharm Bioallied Sci. 2023 Jul-Sep;15(3):139-145. doi: 10.4103/jpbs.jpbs_320_23. Epub 2023 Aug 15. PMID: 37705856; PMCID: PMC10496850. 4: Seng KY, Hee KH, Soon GH, Chew N, Khoo SH, Lee LS. Population pharmacokinetic analysis of isoniazid, acetylisoniazid, and isonicotinic acid in healthy volunteers. Antimicrob Agents Chemother. 2015 Nov;59(11):6791-9. doi: 10.1128/AAC.01244-15. Epub 2015 Aug 17. PMID: 26282412; PMCID: PMC4604378. 5: Wang P, Pradhan K, Zhong XB, Ma X. Isoniazid metabolism and hepatotoxicity. Acta Pharm Sin B. 2016 Sep;6(5):384-392. doi: 10.1016/j.apsb.2016.07.014. Epub 2016 Aug 3. PMID: 27709007; PMCID: PMC5045547. 6: Hutchings AD, Monie RD, Spragg BP, Routledge PA. Saliva and plasma concentrations of isoniazid and acetylisoniazid in man. Br J Clin Pharmacol. 1988 May;25(5):585-9. doi: 10.1111/j.1365-2125.1988.tb03349.x. PMID: 3408638; PMCID: PMC1386432. 7: Zhou Z, Chen L, Liu P, Shen M, Zou F. Simultaneous determination of isoniazid, pyrazinamide, rifampicin and acetylisoniazid in human plasma by high- performance liquid chromatography. Anal Sci. 2010;26(11):1133-8. doi: 10.2116/analsci.26.1133. PMID: 21079341. 8: Huffman DH, Dujovne CA. The instability of isoniazid and acetylisoniazid in frozen plasma. Res Commun Chem Pathol Pharmacol. 1976 Sep;15(1):203-4. PMID: 968176. 9: Ellard GA, Gammon PT, Wallace SM. The determination of isoniazid and its metabolites acetylisoniazid, monoacetylhydrazine, diacetylhydrazine, isonicotinic acid and isonicotinylglycine in serum and urine. Biochem J. 1972 Feb;126(3):449-58. doi: 10.1042/bj1260449. PMID: 5075259; PMCID: PMC1178399. 10: Guermouche S, Guermouche MH. Solid-phase extraction and HPTLC determination of isoniazid and acetylisoniazid in serum. Comparison with HPLC. J Chromatogr Sci. 2004 May-Jun;42(5):250-3. doi: 10.1093/chromsci/42.5.250. PMID: 15189597. 11: Sarma GR, Immanuel C, Kailasam S, Kannapiran M, Nair NG, Radhakrishna S. A modified method for the estimation of acetylisoniazid in urine. Indian J Med Res. 1974 Jun;62(6):945-52. PMID: 4435909. 12: Bing C, Xiaomeia C, Jinhenga L. Gene dose effect of NAT2 variants on the pharmacokinetics of isoniazid and acetylisoniazid in healthy Chinese subjects. Drug Metabol Drug Interact. 2011;26(3):113-8. doi: 10.1515/DMDI.2011.016. PMID: 21980963. 13: Nageswara Rao KV, Eidus L, Jacob CV, Radhakrishna S, Tripathy SP. Sodium nitroprusside test for the detection of isoniazid and acetylisoniazid in urine. Tubercle. 1967 Mar;48(1):45-50. doi: 10.1016/s0041-3879(67)80051-5. PMID: 4166512. 14: Seifart HI, Gent WL, Parkin DP, van Jaarsveld PP, Donald PR. High- performance liquid chromatographic determination of isoniazid, acetylisoniazid and hydrazine in biological fluids. J Chromatogr B Biomed Appl. 1995 Dec 15;674(2):269-75. doi: 10.1016/0378-4347(96)82886-6. PMID: 8788156. 15: Ng KY, Zhou H, Zhang YL, Hybertson B, Randolph T, Christians U. Quantification of isoniazid and acetylisoniazid in rat plasma and alveolar macrophages by liquid chromatography-tandem mass spectrometry with on-line extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Mar 1;847(2):188-98. doi: 10.1016/j.jchromb.2006.10.008. Epub 2006 Oct 27. PMID: 17070115. 16: Jenner PJ, Ellard GA. Isoniazid-related hepatotoxicity: a study of the effect of rifampicin administration on the metabolism of acetylisoniazid in man. Tubercle. 1989 Jun;70(2):93-101. doi: 10.1016/0041-3879(89)90033-0. PMID: 2617692. 17: YARD AS, MCKENNIS H Jr. ASPECTS OF THE METABOLISM OF ISONIAZID AND ACETYLISONIAZID IN THE HUMAN AND THE DOG. J Med Pharm Chem. 1962 Jan;5:196-203. doi: 10.1021/jm01236a019. PMID: 14046608. 18: Hutchings A, Monie RD, Spragg B, Routledge PA. A method to prevent the loss of isoniazid and acetylisoniazid in human plasma. Br J Clin Pharmacol. 1983 Feb;15(2):263-6. doi: 10.1111/j.1365-2125.1983.tb01496.x. PMID: 6849760; PMCID: PMC1427860. 19: Venkataraman P, Menon NK, Nair NG, Radhakrishna S, Ross C, Tripathy SP. Classification of subjects as slow or rapid inactivators of isoniazid, based on the ratio of the urinary excretion of acetylisoniazid to isoniazid. Indian J Med Res. 1972 May;60(5):685-93. PMID: 4663236. 20: Raghupati Sarma G, Kannapirin G, Narayana AS, Radhakrishna S, Tripathy SP. Determination of acetylator phenotype based on the ratio of acetylisoniazid to isoniazid in urine following an oral dose of ordinary isoniazid. Indian J Med Res. 1976 Jan;64(1):1-8. PMID: 1270091.