Alrestatin free acid
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MedKoo CAT#: 592702

CAS#: 51411-04-2 (free acid)

Description: Alrestatin is a specific inhibitor of the aldose reductase enzyme. Alrestatin also inhibited gastric acid secretion and decreased the volume of gastric juice produced in pylorus-ligated rats. It is structurally related to tolrestat, another ARI that was briefly marketed before being withdrawn in 1997.


Chemical Structure

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Alrestatin free acid
CAS# 51411-04-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 592702
Name: Alrestatin free acid
CAS#: 51411-04-2 (free acid)
Chemical Formula: C14H9NO4
Exact Mass: 255.0532
Molecular Weight: 255.229
Elemental Analysis: C, 65.88; H, 3.55; N, 5.49; O, 25.07

Price and Availability

Size Price Availability Quantity
50.0mg USD 250.0 2 Weeks
100.0mg USD 450.0 2 Weeks
200.0mg USD 750.0 2 Weeks
500.0mg USD 1550.0 2 Weeks
1.0g USD 2650.0 2 Weeks
2.0g USD 4650.0 2 Weeks
5.0g USD 6850.0 2 Weeks
Bulk inquiry

Related CAS #: 51876-97-2 (sodium)   51411-04-2 (free acid)    

Synonym: Alrestatin; AY-22284; AY 22284; AY22284; Alrestatin free acid

IUPAC/Chemical Name: 1,3-Dioxo-1H-benz(de)isoquinoline-2(3H)-acetic acid

InChi Key: GCUCIFQCGJIRNT-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)

SMILES Code: O=C(O)CN(C(C1=CC=CC2=CC=CC3=C12)=O)C3=O

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

Preparing Stock Solutions

The following data is based on the product molecular weight 255.229 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

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1: Gabbay KH, Spack N, Loo S, Hirsch HJ, Ackil AA. Aldose reductase inhibition: studies with alrestatin. Metabolism. 1979 Apr;28(4 Suppl 1):471-6. PubMed PMID: 122298.

2: Ehrig T, Bohren KM, Prendergast FG, Gabbay KH. Mechanism of aldose reductase inhibition: binding of NADP+/NADPH and alrestatin-like inhibitors. Biochemistry. 1994 Jun 14;33(23):7157-65. PubMed PMID: 8003482.

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4: Lippmann W, Kobric M. Effect of alrestatin on arginine-induced secretion of glucagon and insulin in the rat. Horm Metab Res. 1978 Jul;10(4):280-2. PubMed PMID: 98419.

5: Lippmann W, Seethaler K, Borella LE, Pugsley TA. Alrestatin: gastric acid antisecretory-antiulcer activity in the rat. Digestion. 1978;18(1-2):35-44. PubMed PMID: 103765.

6: Chylack LT Jr, Henriques HF 3rd, Cheng HM, Tung WH. Efficacy of Alrestatin, an aldose reductase inhibitor, in human diabetic and nondiabetic lenses. Ophthalmology. 1979 Sep;86(9):1579-85. PubMed PMID: 121768.

7: Lippmann W. Inhibition of prostaglandin-induced cyclic AMP accumulation in the rat anterior pituitary by alrestatin. Experientia. 1978 Apr 15;34(4):441-3. PubMed PMID: 205429.

8: Maragoudakis ME, Wasvary J, Hankin H, Gargiulo P. Human placenta aldose reductase. Forms sensitive and insensitive to inhibition by alrestatin. Mol Pharmacol. 1984 May;25(3):425-30. PubMed PMID: 6427599.

9: Harrison DH, Bohren KM, Petsko GA, Ringe D, Gabbay KH. The alrestatin double-decker: binding of two inhibitor molecules to human aldose reductase reveals a new specificity determinant. Biochemistry. 1997 Dec 23;36(51):16134-40. PubMed PMID: 9405046.

10: Distiller LA, Joffe BI, Sandler M, Kark A, Seftel HC. The effect of alrestatin on alanine-stimulated release of insulin and glucagon in man. J Endocrinol Invest. 1981 Jan-Mar;4(1):115-7. PubMed PMID: 6787107.

11: O'Brien MM, Schofield PJ, Edwards MR. Inhibition of human brain aldose reductase and hexonate dehydrogenase by alrestatin and sorbinil. J Neurochem. 1982 Sep;39(3):810-4. PubMed PMID: 6808090.

12: Bhatnagar A, Liu SQ, Das B, Ansari NH, Srivastava SK. Inhibition kinetics of human kidney aldose and aldehyde reductases by aldose reductase inhibitors. Biochem Pharmacol. 1990 Mar 15;39(6):1115-24. PubMed PMID: 2157439.

13: Grewal AS, Bhardwaj S, Pandita D, Lather V, Sekhon BS. Updates on Aldose Reductase Inhibitors for Management of Diabetic Complications and Non-diabetic Diseases. Mini Rev Med Chem. 2016;16(2):120-62. Review. PubMed PMID: 26349493.

14: DeRuiter J, Swearingen BE, Wandrekar V, Mayfield CA. Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety. J Med Chem. 1989 May;32(5):1033-8. PubMed PMID: 2496229.

15: Srivastava SK, Petrash JM, Sadana IJ, Ansari NH, Partridge CA. Susceptibility of aldehyde and aldose reductases of human tissues to aldose reductase inhibitors. Curr Eye Res. 1982-1983;2(6):407-10. PubMed PMID: 6820339.

16: Fagius J, Jameson S. Effects of aldose reductase inhibitor treatment in diabetic polyneuropathy - a clinical and neurophysiological study. J Neurol Neurosurg Psychiatry. 1981 Nov;44(11):991-1001. PubMed PMID: 6801211; PubMed Central PMCID: PMC491202.

17: Tsai SC, Burnakis TG. Aldose reductase inhibitors: an update. Ann Pharmacother. 1993 Jun;27(6):751-4. Review. PubMed PMID: 8329799.

18: Katoh Y, Takebayashi K, Kikuchi A, Iki A, Kikuchi K, Tamba M, Kawashima A, Matsuda M, Okamura N. Porcine sperm capacitation involves tyrosine phosphorylation and activation of aldose reductase. Reproduction. 2014 Oct;148(4):389-401. doi: 10.1530/REP-14-0199. Epub 2014 Jul 21. PubMed PMID: 25049426.

19: De Jongh KS, Schofield PJ, Edwards MR. Kinetic mechanism of sheep liver NADPH-dependent aldehyde reductase. Biochem J. 1987 Feb 15;242(1):143-50. PubMed PMID: 3593233; PubMed Central PMCID: PMC1147676.

20: Keightley JA, Shang L, Kinter M. Proteomic analysis of oxidative stress-resistant cells: a specific role for aldose reductase overexpression in cytoprotection. Mol Cell Proteomics. 2004 Feb;3(2):167-75. Epub 2003 Dec 15. PubMed PMID: 14676331.