Synonym
Azosulfamide; NSC 402615; NSC-402615; NSC402615; Streptozon II; Streptozon S; Disodium Neoprontosil;
IUPAC/Chemical Name
sodium (E)-6-acetamido-4-hydroxy-3-((4-sulfamoylphenyl)diazenyl)naphthalene-2,7-disulfonate
InChi Key
YAZZWQFMIGUHKS-ZPZFBZIMSA-L
InChi Code
InChI=1S/C18H16N4O10S3.2Na/c1-9(23)20-14-8-13-10(6-15(14)34(27,28)29)7-16(35(30,31)32)17(18(13)24)22-21-11-2-4-12(5-3-11)33(19,25)26;;/h2-8,24H,1H3,(H,20,23)(H2,19,25,26)(H,27,28,29)(H,30,31,32);;/q;2*+1/p-2/b22-21+;;
SMILES Code
O=S(C1=C(/N=N/C2=CC=C(S(=O)(N)=O)C=C2)C(O)=C3C=C(NC(C)=O)C(S(=O)([O-])=O)=CC3=C1)([O-])=O.[Na+].[Na+]
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
588.48
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: MEONI S, BRUCOLI V, BIAGI G. [THE AZOSULFAMIDE TEST AS A LIVER FUNCTION TEST]. Fegato. 1963 Dec;18:421-31. Italian. PubMed PMID: 14117141.
2: MOLLERBERG HL, BOTTIGER LE. The azosulfamide (neoprontosii) test in clinical evaluation of liver function. AMA Arch Intern Med. 1959 Jun;103(6):949-53. PubMed PMID: 13648997.
3: ORREGO H, TAG F, PALMA R, INZUNZA I, NAVIA E. [Diagnostic value of the urinary excretion of azosulfamide in hepatic diseases]. Rev Med Chil. 1962 Mar;90:230-8. Spanish. PubMed PMID: 14482351.
4: BEGRUP H, HALD A, LINDAHL A. [Liver function test with azosulfamide]. Ugeskr Laeger. 1963 Jun 21;125:890-2. Danish. PubMed PMID: 13970269.
5: MacAllister CG, Perdue BD. Endoscopic diagnosis of unilateral ectopic ureter in a yearling filly. J Am Vet Med Assoc. 1990 Sep 1;197(5):617-8. PubMed PMID: 2211312.
6: Bryant JS, Gausche-Hill M. When is red urine not hematuria?: A case report. J Emerg Med. 2007 Jan;32(1):55-7. PubMed PMID: 17239733.
7: Shargel L, Banijamali AR, Kuttab SH. Relationship between azo dye structure and rat hepatic azoreductase activity. J Pharm Sci. 1984 Feb;73(2):161-4. PubMed PMID: 6707875.
8: Gingell R, Bridges JW, Williams RT. The role of the gut flora in the metabolism of prontosil and neoprontosil in the rat. Xenobiotica. 1971 Mar;1(2):143-56. PubMed PMID: 5173017.
9: Carey PR, King RW. Neoprontosil binding to carbonic anhydrase. Reasonance Raman and other studies on the ionization behavior of the sulfonamide. Biochemistry. 1979 Jun 26;18(13):2834-8. PubMed PMID: 38830.
10: Thompson RB, Patchan MW. Lifetime-based fluorescence energy transfer biosensing of zinc. Anal Biochem. 1995 May 1;227(1):123-8. PubMed PMID: 7668370.
11: SCUDERI G, BELLOMIO S. [Comparative experimental clinical research on the effect of chloramphenicol, azosulfamides and penicillin in trachoma]. Arch Sci Med (Torino). 1951 Sep;92(3):152-74. Undetermined Language. PubMed PMID: 14904246.
12: Douglas KL, Walker RV. Use of Neo-Prontosil in Strangles. Can J Comp Med. 1939 Jun;3(6):166-9. PubMed PMID: 17647531; PubMed Central PMCID: PMC1702136.
13: Wilson ID, Nicholson JK. Gut microbiome interactions with drug metabolism, efficacy, and toxicity. Transl Res. 2017 Jan;179:204-222. doi: 10.1016/j.trsl.2016.08.002. Epub 2016 Aug 13. Review. PubMed PMID: 27591027; PubMed Central PMCID: PMC5718288.
14: Kendrick DB. TREATMENT OF GAS GANGRENE INFECTIONS IN GUINEA-PIGS WITH NEOPRONTOSIL, SULFANILAMIDE, AND SULFAPYRIDINE: AN EXPERIMENTAL STUDY. J Clin Invest. 1939 Sep;18(5):593-6. PubMed PMID: 16694690; PubMed Central PMCID: PMC434904.
15: Chung KT, Stevens SE Jr, Cerniglia CE. The reduction of azo dyes by the intestinal microflora. Crit Rev Microbiol. 1992;18(3):175-90. Review. PubMed PMID: 1554423.
16: Evelhoch JL, Bocian DF, Sudmeier JL. Evidence for direct metal-nitrogen binding in aromatic sulfonamide complexes of cadmium (II)-substituted carbonic anhydrases by cadmium-113 nuclear magnetic resonance. Biochemistry. 1981 Aug 18;20(17):4951-4. PubMed PMID: 6794601.
17: Petersen RL, Li TY, McFarland JT, Watters KL. Determination of ionization state by resonance Raman spectroscopy Sulfonamide binding to carbonic anhydrase. Biochemistry. 1977 Feb 22;16(4):726-31. PubMed PMID: 13824.
18: Osborne WR, Tashian RE. Dissociation constants for carbonic anhydrase--sulfonamide binding by high-performance liquid chromatography. Anal Biochem. 1984 Mar;137(2):302-6. PubMed PMID: 6428265.
19: Ericksson M, Catz C, Yaffe SJ. Effect of weanling malnutrition upon hepatic drug metabolism. Biol Neonate. 1975;27(5-6):339-51. PubMed PMID: 1174605.
20: Osborne WR, Tashian RE. The proteolytic degradation of normal and variant human carbonic anhydrase isozymes by alpha-chymotrypsin. J Biol Chem. 1981 Feb 10;256(3):1330-4. PubMed PMID: 6778879.
