MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318769 | Name: Sulfamethoxazole
Featured New

Description:

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

Sulfamethoxazole is an antibiotic. It was used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Listeria monocytogenes and E. coli. Common side effects include nausea, vomiting, loss of appetite, and a rash. It is a sulfonamide and bacteriostatic.

Chemical Structure

Sulfamethoxazole
Sulfamethoxazole
CAS#723-46-6

Theoretical Analysis

MedKoo Cat#: 318769

Name: Sulfamethoxazole

CAS#: 723-46-6

Chemical Formula: C10H11N3O3S

Exact Mass: 253.0521

Molecular Weight: 253.28

Elemental Analysis: C, 47.42; H, 4.38; N, 16.59; O, 18.95; S, 12.66

Price and Availability

Size Price Availability Quantity
1g USD 90.00 Ready to ship
5g USD 150.00 Ready to ship
10g USD 225.00 Ready to ship
20g USD 350.00 Ready to ship
50g USD 550.00 Ready to ship
500g USD 1,450.00 2 weeks
1kg USD 2,450.00 2 weeks
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
RP-2145; RP2145; RP 2145; Sulfamethoxazole; Rufol; Salimol
IUPAC/Chemical Name
4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide
InChi Key
JLKIGFTWXXRPMT-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
SMILES Code
CC1=CC(NS(=O)(C2=CC=C(N)C=C2)=O)=NO1
Appearance
Solid powder
Purity
>99% (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
2934.99.4400
More Info
Biological target:
Sulfamethoxazole (Ro 4-2130) is a sulfonamide bacteriostatic antibiotic, used for bacterial infections.
In vitro activity:
Dendritic cells exposed to SMX (Sulfamethoxazole) (maximal effect: 250–500 μM) and SMX-NO (maximal effect: 1 μM) consistently displayed a concentration-dependent increase in CD40 expression (Fig. 2⇓), but no increase in CD80, CD83, or CD86 (Fig. 2⇓A). In contrast, cells exposed to LPS showed an increase in expression of all the markers examined. Importantly, the response to SMX and SMX-NO was unaffected by preincubation with polymyxin B (20 μg/ml), whereas the response to LPS was completely eliminated (data not shown). As polymyxin B readily binds to and inactivates LPS, these data show that the observed response was not due to LPS contamination of the stock compounds. Reference: J Immunol. 2007 May 1;178(9):5533-42. https://www.jimmunol.org/content/178/9/5533.long
In vivo activity:
In untreated GKO C57BL/6 mice (G1) on day 7 PI (Figs. 3a 3b 3c 3d 3e 3f 3g 3h) , the kinetics of T. gondii loads showed that it was detected in all organs and tissues examined except the peripheral retina. In untreated GKO BALB/c mice (G1), the kinetic patterns of the abundance of protozoan in the organs and tissues were similar to those in untreated GKO C57BL/6 mice (Figs. 3i 3j 3k 3l 3m 3n 3o 3p) . T. gondii DNA was not detected in any of these organs and tissues except the brain under continuous SMX (Sulfamethoxazole) treatment. It should be noted that even in the brain, the T. gondii load tended to decline under continuous treatment, but the protozoan began to proliferate after its cessation. Reference: Toxicology. 2005 Jan 15;206(2):221-31. https://pubmed.ncbi.nlm.nih.gov/15588915/
Solvent mg/mL mM
Solubility
DMSO 67.0 264.53
DMSO:PBS (pH 7.2) (1:2) 0.5 1.97
DMF 50.0 197.41
Ethanol 11.6 45.92
Water 0.1 0.39
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 253.28 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:
1. Sanderson JP, Naisbitt DJ, Farrell J, Ashby CA, Tucker MJ, Rieder MJ, Pirmohamed M, Clarke SE, Park BK. Sulfamethoxazole and its metabolite nitroso sulfamethoxazole stimulate dendritic cell costimulatory signaling. J Immunol. 2007 May 1;178(9):5533-42. doi: 10.4049/jimmunol.178.9.5533. PMID: 17442935. 2. Norose K, Aosai F, Mun HS, Yano A. Effects of sulfamethoxazole on murine ocular toxoplasmosis in interferon-gamma knockout mice. Invest Ophthalmol Vis Sci. 2006 Jan;47(1):265-71. doi: 10.1167/iovs.05-0751. PMID: 16384972. 3. Hopkins JE, Naisbitt DJ, Humphreys N, Dearman RJ, Kimber I, Park BK. Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Toxicology. 2005 Jan 15;206(2):221-31. doi: 10.1016/j.tox.2004.08.010. PMID: 15588915.
In vitro protocol:
1. Sanderson JP, Naisbitt DJ, Farrell J, Ashby CA, Tucker MJ, Rieder MJ, Pirmohamed M, Clarke SE, Park BK. Sulfamethoxazole and its metabolite nitroso sulfamethoxazole stimulate dendritic cell costimulatory signaling. J Immunol. 2007 May 1;178(9):5533-42. doi: 10.4049/jimmunol.178.9.5533. PMID: 17442935.
In vivo protocol:
1. Norose K, Aosai F, Mun HS, Yano A. Effects of sulfamethoxazole on murine ocular toxoplasmosis in interferon-gamma knockout mice. Invest Ophthalmol Vis Sci. 2006 Jan;47(1):265-71. doi: 10.1167/iovs.05-0751. PMID: 16384972. 2. Hopkins JE, Naisbitt DJ, Humphreys N, Dearman RJ, Kimber I, Park BK. Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Toxicology. 2005 Jan 15;206(2):221-31. doi: 10.1016/j.tox.2004.08.010. PMID: 15588915.
1: Michałek K, Lechowicz M, Pastuszczak M, Wojas-Pelc A. The use of trimethoprim and sulfamethoxazole (TMP-SMX) in dermatology. Folia Med Cracov. 2015;55(1):35-41. Review. PubMed PMID: 26774630. 2: Falagas ME, Vardakas KZ, Roussos NS. Trimethoprim/sulfamethoxazole for Acinetobacter spp.: A review of current microbiological and clinical evidence. Int J Antimicrob Agents. 2015 Sep;46(3):231-41. doi: 10.1016/j.ijantimicag.2015.04.002. Epub 2015 May 15. Review. PubMed PMID: 26070662. 3: Straub JO. Aquatic environmental risk assessment for human use of the old antibiotic sulfamethoxazole in Europe. Environ Toxicol Chem. 2016 Apr;35(4):767-79. doi: 10.1002/etc.2945. Epub 2015 May 22. Review. PubMed PMID: 25693841. 4: Bruner KE, Coop CA, White KM. Trimethoprim-sulfamethoxazole-induced aseptic meningitis-not just another sulfa allergy. Ann Allergy Asthma Immunol. 2014 Nov;113(5):520-6. doi: 10.1016/j.anai.2014.08.006. Epub 2014 Sep 17. Review. PubMed PMID: 25240332. 5: Tu GW, Ju MJ, Xu M, Rong RM, He YZ, Xue ZG, Zhu TY, Luo Z. Combination of caspofungin and low-dose trimethoprim/sulfamethoxazole for the treatment of severe Pneumocystis jirovecii pneumonia in renal transplant recipients. Nephrology (Carlton). 2013 Nov;18(11):736-42. doi: 10.1111/nep.12133. Review. PubMed PMID: 24571744. 6: Hale SF, Lesar TS. Interaction of vitamin K antagonists and trimethoprim-sulfamethoxazole: ignore at your patient's risk. Drug Metabol Drug Interact. 2014;29(1):53-60. doi: 10.1515/dmdi-2013-0049. Review. PubMed PMID: 24231121. 7: Hsiao HH, Chu NS, Tsai YF, Chang CS, Lin SF, Liu TC. Trimethoprim/sulfamethoxazole-related acute psychosis in the second course of treatment after a stem cell transplant: case report and literature review. Exp Clin Transplant. 2013 Oct;11(5):467-8. Review. PubMed PMID: 24128138. 8: Cunha BA. Minocycline, often forgotten but preferred to trimethoprim-sulfamethoxazole or doxycycline for the treatment of community-acquired meticillin-resistant Staphylococcus aureus skin and soft-tissue infections. Int J Antimicrob Agents. 2013 Dec;42(6):497-9. doi: 10.1016/j.ijantimicag.2013.08.006. Epub 2013 Sep 13. Review. PubMed PMID: 24126085. 9: Di Carlo P, D'Alessandro N, Guadagnino G, Bonura C, Mammina C, Lunetta M, Novo S, Giarratano A. High dose of trimethoprim-sulfamethoxazole and daptomycin as a therapeutic option for MRSA endocarditis with large vegetation complicated by embolic stroke: a case report and literature review. Infez Med. 2013 Mar;21(1):45-9. Review. PubMed PMID: 23524901. 10: Bodro M, Paterson DL. Has the time come for routine trimethoprim-sulfamethoxazole prophylaxis in patients taking biologic therapies? Clin Infect Dis. 2013 Jun;56(11):1621-8. doi: 10.1093/cid/cit071. Epub 2013 Feb 7. Review. PubMed PMID: 23392396. 11: Larcher S, Yargeau V. Biodegradation of sulfamethoxazole: current knowledge and perspectives. Appl Microbiol Biotechnol. 2012 Oct;96(2):309-18. doi: 10.1007/s00253-012-4326-3. Epub 2012 Aug 17. Review. PubMed PMID: 22899494. 12: Ho JM, Juurlink DN. Considerations when prescribing trimethoprim-sulfamethoxazole. CMAJ. 2011 Nov 8;183(16):1851-8. doi: 10.1503/cmaj.111152. Epub 2011 Oct 11. Review. PubMed PMID: 21989472; PubMed Central PMCID: PMC3216436. 13: Sibanda EL, Weller IV, Hakim JG, Cowan FM. Does trimethoprim-sulfamethoxazole prophylaxis for HIV induce bacterial resistance to other antibiotic classes? Results of a systematic review. Clin Infect Dis. 2011 May;52(9):1184-94. doi: 10.1093/cid/cir067. Review. PubMed PMID: 21467024; PubMed Central PMCID: PMC3070868. 14: Di Cocco P, Orlando G, Bonanni L, D'Angelo M, Clemente K, Greco S, Gravante G, Madeddu F, Scelzo C, Famulari A, Pisani F. A systematic review of two different trimetoprim-sulfamethoxazole regimens used to prevent Pneumocystis jirovecii and no prophylaxis at all in transplant recipients: appraising the evidence. Transplant Proc. 2009 May;41(4):1201-3. doi: 10.1016/j.transproceed.2009.03.004. Review. PubMed PMID: 19460516. 15: Pappas G, Athanasoulia AP, Matthaiou DK, Falagas ME. Trimethoprim-sulfamethoxazole for methicillin-resistant Staphylococcus aureus: a forgotten alternative? J Chemother. 2009 Apr;21(2):115-26. Review. PubMed PMID: 19423463. 16: Faria LC, Resende CC, Couto CA, Couto OF, Fonseca LP, Ferrari TC. Severe and prolonged cholestasis caused by trimethoprim-sulfamethoxazole: a case report. Clinics (Sao Paulo). 2009;64(1):71-4. Review. PubMed PMID: 19142556; PubMed Central PMCID: PMC2671966. 17: Sud B, Salvaggio M, Greenfield R, Bronze MS. Part XI. Trimethoprim-sulfamethoxazole, nitrofurantoin, chloramphenicol, metronidazole and tinidazole, rifaximin, and nitazoxanide. J Okla State Med Assoc. 2007 Jul;100(7):267-72. Review. Erratum in: J Okla State Med Assoc. 2007 Oct;100(10):405. Greenfield, Ronald A [corrected to Greenfield, Ronald]. PubMed PMID: 17896614. 18: Bhambri S, Del Rosso JQ, Desai A. Oral trimethoprim/sulfamethoxazole in the treatment of acne vulgaris. Cutis. 2007 Jun;79(6):430-4. Review. PubMed PMID: 17713145. 19: Walker S, Norwood J, Thornton C, Schaberg D. Trimethoprim-sulfamethoxazole associated rhabdomyolysis in a patient with AIDS: case report and review of the literature. Am J Med Sci. 2006 Jun;331(6):339-41. Review. PubMed PMID: 16775445. 20: Forna F, McConnell M, Kitabire FN, Homsy J, Brooks JT, Mermin J, Weidle PJ. Systematic review of the safety of trimethoprim-sulfamethoxazole for prophylaxis in HIV-infected pregnant women: implications for resource-limited settings. AIDS Rev. 2006 Jan-Mar;8(1):24-36. Review. PubMed PMID: 16736949.