Tolazamide
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MedKoo CAT#: 318883

CAS#: 1156-19-0

Description: Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).


Chemical Structure

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Tolazamide
CAS# 1156-19-0

Theoretical Analysis

MedKoo Cat#: 318883
Name: Tolazamide
CAS#: 1156-19-0
Chemical Formula: C14H21N3O3S
Exact Mass: 311.13
Molecular Weight: 311.400
Elemental Analysis: C, 54.00; H, 6.80; N, 13.49; O, 15.41; S, 10.30

Price and Availability

Size Price Availability Quantity
500mg USD -1
100mg USD 450
200mg USD 850
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Synonym: Tolazamide, Tolinase, Norglycin, Tolanase, Tolazolamide

IUPAC/Chemical Name: 1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea

InChi Key: OUDSBRTVNLOZBN-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)

SMILES Code: O=C(NS(=O)(C1=CC=C(C)C=C1)=O)NN2CCCCCC2

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, not in water

Shelf Life: >2 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 311.40 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Boldyreva EV, Arkhipov SG, Drebushchak TN, Drebushchak VA, Losev EA, Matvienko AA, Minkov VS, Rychkov DA, Seryotkin YV, Stare J, Zakharov BA. Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study. Chemistry. 2015 Oct 19;21(43):15395-404. doi: 10.1002/chem.201501541. Epub 2015 Sep 4. PubMed PMID: 26337712.

2: Gao Y, Olsen KW. Drug-polymer interactions at water-crystal interfaces and implications for crystallization inhibition: molecular dynamics simulations of amphiphilic block copolymer interactions with tolazamide crystals. J Pharm Sci. 2015 Jul;104(7):2132-41. doi: 10.1002/jps.24442. Epub 2015 Jun 4. PubMed PMID: 26045147.

3: Schmitt JK, Johns SB. Altering therapy of type II diabetes mellitus from insulin to tolazamide increases blood pressure in spite of weight loss. Am J Hypertens. 1995 May;8(5 Pt 1):520-3. PubMed PMID: 7662230.

4: Sanders R, Faro B, Stoler P, Mick GJ, McCormick KL. Adjunctive use of tolazamide in newly-diagnosed diabetic children. Horm Metab Res. 1990 Nov;22(11):576-80. PubMed PMID: 2272604.

5: Lev JD, Zeidler A, Kumar D. Glyburide and glipizide in treatment of diabetic patients with secondary failures to tolazamide or chlorpropamide. Diabetes Care. 1987 Nov-Dec;10(6):679-82. PubMed PMID: 3123183.

6: Firth R, Bell P, Marsh M, Rizza RA. Effects of tolazamide and exogenous insulin on pattern of postprandial carbohydrate metabolism in patients with non-insulin-dependent diabetes mellitus. Results of randomized crossover trial. Diabetes. 1987 Oct;36(10):1130-8. PubMed PMID: 3308584.

7: Severin G. Monitoring a potential carcinogen in pharmaceutical formulations at the low part per billion level. High-performance liquid chromatographic determination of N-nitrosohexamethyleneimine in tolazamide. J Chromatogr. 1987 Jan 16;386:57-63. PubMed PMID: 3558617.

8: Mukherjee AB, Ghazanfari A, Svoronos S, Staton RC, Nakada T, Kwee IL. Transketolase abnormality in tolazamide-induced Wernicke's encephalopathy. Neurology. 1986 Nov;36(11):1508-10. PubMed PMID: 3762968.

9: Ismail S, el-Zaher AA. Dissolution behaviour of tolazamide in the presence of certain non-ionic surfactants. J Pharm Belg. 1986 Sep-Oct;41(5):308-13. PubMed PMID: 3806351.

10: Skillman CA, Fletcher HP. 2-Deoxyglucose tissue levels and insulin levels following tolazamide dosing in normal and obese mice. Exp Clin Endocrinol. 1986 Aug;87(3):288-98. PubMed PMID: 3536534.

11: Firth RG, Bell PM, Rizza RA. Effects of tolazamide and exogenous insulin on insulin action in patients with non-insulin-dependent diabetes mellitus. N Engl J Med. 1986 May 15;314(20):1280-6. PubMed PMID: 3517644.

12: Reich A, Abraira C, Brunken R, Soneru I. Potentiation of glucose-stimulated insulin release by tolazamide and paradoxical absence of glucose facilitation (Staub effect) in non-insulin-dependent diabetes. Metabolism. 1986 Apr;35(4):367-70. PubMed PMID: 3515119.

13: Kabadi UM. Adjuvant therapy with tolazamide and insulin improves metabolic control in type I diabetes mellitus. Diabetes Care. 1985 Sep-Oct;8(5):440-6. PubMed PMID: 3902422.

14: Nakao NL, Gelb AM, Stenger RJ, Siegel JH. A case of chronic liver disease due to tolazamide. Gastroenterology. 1985 Jul;89(1):192-5. PubMed PMID: 4007403.

15: Barnett JH, Barnett SM. Lichenoid drug reactions to chlorpropamide and tolazamide. Cutis. 1984 Dec;34(6):542-4. PubMed PMID: 6240374.

16: Welling PG, Patel RB, Patel UR, Gillespie WR, Craig WA, Albert KS. Bioavailability of tolazamide from tablets: comparison of in vitro and in vivo results. J Pharm Sci. 1982 Nov;71(11):1259-63. PubMed PMID: 7175719.

17: Bondi E, Slater S. Tolazamide-induced chronic eosinophilic pneumonia. Chest. 1981 Nov;80(5):652. PubMed PMID: 7297166.

18: Levy WJ, Sheeler LR. Surreptitious hypoglycemia secondary to tolazamide. South Med J. 1981 Jan;74(1):63-4. PubMed PMID: 7455744.

19: Bagdade JD, Walters E. Impaired granulocyte adherence in mildly diabetic patients: effects of tolazamide treatment. Diabetes. 1980 Apr;29(4):309-11. PubMed PMID: 7358229.

20: Thomas RC, Duchamp DJ, Judy RW, Ikeda GJ. Metabolic fate of tolazamide in man and in the rat. J Med Chem. 1978 Aug;21(8):725-32. PubMed PMID: 690998.