Gentisamide | CAS#52405-73-9 | salicylamide metabolite

MedKoo Cat#: 145262 | Name: Gentisamide

Description:

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

Gentisamide is a hydroxylated metabolite of salicylamide. Gentisamide is a substrate that forms two monosulfates at the 2 and 5 positions and a monoglucuronide at the 5 position. Gentisamide was used as a model compound to examine the effects of parallel competing pathways on drug disappearance and metabolite formation in the once-through perfused rat liver preparation.

Chemical Structure

Gentisamide

CAS#52405-73-9

Theoretical Analysis

MedKoo Cat#: 145262

Name: Gentisamide

CAS#: 52405-73-9

Chemical Formula: C7H7NO3

Exact Mass: 153.0426

Molecular Weight: 153.14

Elemental Analysis: C, 54.90; H, 4.61; N, 9.15; O, 31.34

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Gentisamide;

IUPAC/Chemical Name

2,5-dihydroxybenzamide

InChi Key

FRXZIFVYTNMCHF-UHFFFAOYSA-N

InChi Code

1S/C7H7NO3/c8-7(11)5-3-4(9)1-2-6(5)10/h1-3,9-10H,(H2,8,11)

SMILES Code

NC(=O)C1=C(O)C=CC(O)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 153.14 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.

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: Morris ME, Yuen V, Pang KS. Competing pathways in drug metabolism. II. An identical, anterior enzymic distribution for 2- and 5-sulfoconjugation and a posterior localization for 5-glucuronidation of gentisamide in the rat liver. J Pharmacokinet Biopharm. 1988 Dec;16(6):633-56. doi: 10.1007/BF01062015. PMID: 3251033. 2: Hirayama H, Pang KS. First-pass metabolism of gentisamide: influence of intestinal metabolism on hepatic formation of conjugates. Studies in the once- through vascularly perfused rat intestine-liver preparation. Drug Metab Dispos. 1990 Sep-Oct;18(5):580-7. PMID: 1981705. 3: Xu X, Tang BK, Pang KS. Sequential metabolism of salicylamide exclusively to gentisamide 5-glucuronide and not gentisamide sulfate conjugates in single-pass in situ perfused rat liver. J Pharmacol Exp Ther. 1990 Jun;253(3):965-73. PMID: 2359032. 4: Morris ME, Levy G. Determination of salicylamide and five metabolites in biological fluids by high-performance liquid chromatography. J Pharm Sci. 1983 Jun;72(6):612-7. doi: 10.1002/jps.2600720609. PMID: 6875820. 5: Morris ME, Yuen V, Tang BK, Pang KS. Competing pathways in drug metabolism. I. Effect of input concentration on the conjugation of gentisamide in the once- through in situ perfused rat liver preparation. J Pharmacol Exp Ther. 1988 May;245(2):614-24. PMID: 3367309. 6: Hirayama H, Morgado J, Gasinska I, Pang KS. Estimations of intestinal and liver first-pass metabolism in vivo. Studies on gentisamide conjugation in the rat. Drug Metab Dispos. 1990 Sep-Oct;18(5):588-94. PMID: 1981706. 7: Xu X, Pang KS. Hepatic modeling of metabolite kinetics in sequential and parallel pathways: salicylamide and gentisamide metabolism in perfused rat liver. J Pharmacokinet Biopharm. 1989 Dec;17(6):645-71. doi: 10.1007/BF01062123. PMID: 2635738. 8: Jadrijević-Mladar Takac M, Vikić Topić D, Govorcinović T. FT-IR and NMR spectroscopic studies of salicylic acid derivatives. I. Gentisamide -- a metabolite of salicylamide. Acta Pharm. 2004 Sep;54(3):163-76. PMID: 15610614. 9: Howell SR, Kotkoskie LA, Dills RL, Klaassen CD. 3-Hydroxylation of salicylamide in mice. J Pharm Sci. 1988 Apr;77(4):309-13. doi: 10.1002/jps.2600770405. PMID: 3379587. 10: DeBlassio JL, deLong MA, Glufke U, Kulathila R, Merkler KA, Vederas JC, Merkler DJ. Amidation of salicyluric acid and gentisuric acid: a possible role for peptidylglycine alpha-amidating monooxygenase in the metabolism of aspirin. Arch Biochem Biophys. 2000 Nov 1;383(1):46-55. doi: 10.1006/abbi.2000.2047. PMID: 11097175. 11: Xu X, Pang KS. High-performance liquid chromatographic method for the quantitation of salicylamide and its metabolites in biological fluids. J Chromatogr. 1987 Sep 25;420(2):313-27. doi: 10.1016/0378-4347(87)80187-1. PMID: 3693503. 12: Tirona RG, Pang KS. Sequestered endoplasmic reticulum space for sequential metabolism of salicylamide. Coupling of hydroxylation and glucuronidation. Drug Metab Dispos. 1996 Aug;24(8):821-33. PMID: 8869815. 13: Morris ME, Levy G. Pharmacodynamics of the hypnotic effect of salicylamide in rats. J Pharm Sci. 1985 Jun;74(6):599-602. doi: 10.1002/jps.2600740603. PMID: 4020644. 14: Xu X, Hirayama H, Pang KS. First-pass metabolism of salicylamide. Studies in the once-through vascularly perfused rat intestine-liver preparation. Drug Metab Dispos. 1989 Sep-Oct;17(5):556-63. PMID: 2573500. 15: Abdel-Rahman MS, Reddi AS, Curro FA, Turkall RM, Kadry AM, Hansrote JA. Bioavailability of aspirin and salicylamide following oral co-administration in human volunteers. Can J Physiol Pharmacol. 1991 Oct;69(10):1436-42. doi: 10.1139/y91-215. PMID: 1777842. 16: Song CS, Gelb NA, Wolff SM. The influence of pyrogen-induced fever on salicylamide metabolism in man. J Clin Invest. 1972 Nov;51(11):2959-66. doi: 10.1172/JCI107120. PMID: 5080420; PMCID: PMC292446. 17: Jadrijević-Mladar Takac M, Vikić Topić D. FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives. Acta Pharm. 2004 Sep;54(3):177-91. PMID: 15610615. 18: Manda K, Gördes D, Mikolasch A, Hammer E, Schmidt E, Thurow K, Schauer F. Carbon-oxygen bond formation by fungal laccases: cross-coupling of 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide with the solvents water, methanol, and other alcohols. Appl Microbiol Biotechnol. 2007 Aug;76(2):407-16. doi: 10.1007/s00253-007-1024-7. Epub 2007 Jun 19. PMID: 17576553.