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Purity: ≥98%
1-Aminobenzotriazole (also known as ABT; 3-Aminobenzotriazole) has been used widely as a nonselective in vitro and in vivo inhibitor of cytochrome P450 enzymes. To date, however, it has not been evaluated as an inhibitor of UDP-glucuronosyltransferase (UGT), sulfotransferase (SULT), and N-acetyltransferase (NAT). ABT was shown not to inhibit UGT and SULT activity (acetaminophen and 7-hydroxycoumarin as substrates) in rat liver microsomes and rat liver 9000 g supernatant fraction (RLS9), respectively. However, it did inhibit the RLS9-catalyzed N-acetylation of procainamide (IC(50) ∼ 30 μM), and no preincubation time dependence was evident. In agreement, oral ABT (100 mg/kg, 2 h predose) decreased the clearance of intravenous procainamide (45%) in rats, accompanied by a decreased N-acetylprocainamide-to-procainamide ratio in urine (0.74 versus 0.21) and plasma (area under the curve ratio 0.59 versus 0.11). Additional studies with human forms of NAT (hNAT1 and hNAT2) revealed that ABT is a more potent inhibitor of hNAT2 compared with hNAT1 (IC(50) 158 μM versus > 1 mM). Consistent with the IC(50) estimate, formal inhibition studies revealed that inhibition of hNAT2 was competitive with an inhibition constant of 67 μM. In accordance with the competitive inhibition, ABT was shown to undergo N-acetylation in the presence of both human NAT forms, with hNAT1 exhibiting less activity under the same assay conditions (∼40% of hNAT2). In summary, the results described herein indicate that ABT is a substrate and inhibitor of NAT. Such an interaction should be considered when using ABT as a nonselective inhibitor of P450, especially when NAT-dependent metabolism is also involved.
| ln Vitro |
1-Aminobenzotriazole (ABT) alone considerably raised the CYP2B6 expression levels in two distinct hepatocytes (by 7.3 and 10.8 fold, respectively). The induction of CYP2B6 expression by CITCO or rifampicin was improved 12.6-fold and 4.0-fold for CITCO and 3.9-fold and 2.5-fold for rifampicin following co-treatment with 1-aminobenzotriazole. 1-Aminobenzotriazole has a more stimulating impact on CITCO than rifampicin does. 1. In two distinct hepatocytes, aminobenzotriazole alone elevated the expression levels of CYP3A4 by 2.0 and 3.8 times, respectively. The effect of CITCO on CYP3A4 expression levels was increased by 3.8 and 6.0 times after co-treatment with 1-aminobenzotriazole, respectively, in comparison to cells treated with CITCO alone [1]. When compared to a clear 1-aminobenzotriazole control, 1-aminobenzotriazole (ABT) (1 mM) demonstrated a significant (~95%) improvement in the production of N-CPU-based procainamide[2].
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| ln Vivo |
Wall 1-aminobenzotriazole (ABT) (100 mg/kg, 2 hours before laboratory) decreases the rate of intravenous procainamide clearance (45%), but N-aminobenzotriazole waste Reduced area under the curve ratio of 0.59 compared to 0.11 and decreased ratio of inamide to procainamide (0.74 vs. 0.21). The recovery of N-benzoprocainamide in stealing dropped from 13.3% to 6.5%, whereas the residual recovery of procainamide increased from 18% to 30% when 1-aminobenzotriazole was used [2]. Gastric emptying was markedly delayed by a pretreatment of 100 mg/kg oral 1-aminobenzotriazole (ABT), given two hours prior to a semi-solid caloric test meal. 1-Aminobenzotriazole also doubles the amount of space in the stomach [3].
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| References |
[1]. Yang K, et al. Induction of CYP2B6 and CYP3A4 expression by 1-aminobenzotriazole (ABT) in human hepatocytes. Drug Metab Lett. 2010 Aug;4(3):129-33.
[2]. Sun Q, et al. 1-Aminobenzotriazole, a known cytochrome P450 inhibitor, is a substrate and inhibitor of N-acetyltransferase. Drug Metab Dispos. 2011 Sep;39(9):1674-9. [3]. Stringer RA, et al. 1-Aminobenzotriazole modulates oral drug pharmacokinetics through cytochrome P450 inhibition and delay of gastric emptying in rats. Drug Metab Dispos. 2014 Jul;42(7):1117-24 |
| Molecular Formula |
C6H6N4
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|---|---|
| Molecular Weight |
134.1386
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| CAS # |
1614-12-6
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| SMILES |
NN1N=NC2=CC=CC=C21
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| Synonyms |
1-Aminobenzotriazole; ABT; 3-Aminobenzotriazole
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~745.49 mM)
H2O : ~50 mg/mL (~372.74 mM) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.4549 mL | 37.2745 mL | 74.5490 mL | |
| 5 mM | 1.4910 mL | 7.4549 mL | 14.9098 mL | |
| 10 mM | 0.7455 mL | 3.7274 mL | 7.4549 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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