Sulbenicillin | CAS#41744-40-5 | antibiotic

MedKoo Cat#: 558200 | Name: Sulbenicillin

Description:

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

Sulbenicillin is an alpha-sulfobenzylpenicillin and it has been used in combination with dibekacin.

Chemical Structure

Sulbenicillin

CAS#41744-40-5

Theoretical Analysis

MedKoo Cat#: 558200

Name: Sulbenicillin

CAS#: 41744-40-5

Chemical Formula: C16H18N2O7S2

Exact Mass: 414.0600

Molecular Weight: 414.45

Elemental Analysis: C, 46.37; H, 4.38; N, 6.76; O, 27.02; S, 15.47

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

Sulbenicillin; Kedacillin; Kedacillina; Sulbenicilina;

IUPAC/Chemical Name

3,3-Dimethyl-7-oxo-6-(2-phenyl-2-sulfoacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

InChi Key

JETQIUPBHQNHNZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H18N2O7S2/c1-16(2)11(15(21)22)18-13(20)9(14(18)26-16)17-12(19)10(27(23,24)25)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,17,19)(H,21,22)(H,23,24,25)

SMILES Code

O=C(C(C(C)(C)SC1C2NC(C(C3=CC=CC=C3)S(=O)(O)=O)=O)N1C2=O)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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 414.45 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: Ripa S, Mignini F, Patrizi I, Ferrante L, Prenna M, Falcioni E. Sulbenicillin: pharmacokinetics and penetration into bronchial secretion in elderly patients. Chemioterapia. 1987 Aug;6(4):277-81. PubMed PMID: 3652279. 2: Liu W, Zhao XM, Zhang HB, Zhang L, Zhao MZ. Asymmetric synthesis of allylic sulfonic acids: enantio- and regioselective iridium-catalyzed allylations of Na2SO3. Chemistry. 2014 Dec 15;20(51):16873-6. doi: 10.1002/chem.201405058. Epub 2014 Nov 3. PubMed PMID: 25367779. 3: Aonuma S, Ariji F, Oizumi K, Konno K. Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin. Tohoku J Exp Med. 1987 Jun;152(2):119-28. PubMed PMID: 3114912. 4: Kjellander J, Lanner A, Norrby R. Bacteriological and clinical studies of sulbenicillin. Scand J Infect Dis. 1978;10(3):235-41. PubMed PMID: 362518. 5: Ikeda Y, Kikuchi M, Matsuda S, Toyama K, Hasegawa M, Watanabe K, Ando Y. Inhibition of platelet function by sulbenicillin and its metabolite. Antimicrob Agents Chemother. 1978 May;13(5):881-3. PubMed PMID: 666307; PubMed Central PMCID: PMC352348. 6: Hakamata M, Hozawa J, Saito H, Fukuoka K, Yamagami M, Usami S. [Evaluation of clinical efficacy of sulbenicillin following surgery of malignant maxillary tumors. Transport of sulbenicillin to the exudates from the surgical wound of the maxilla and its therapeutic effects]. Jpn J Antibiot. 1982 May;35(5):1254-60. Japanese. PubMed PMID: 7131758. 7: Takeuchi E, Abe T, Shimizu T, Murase M, Tanaka M, Nogaki H, Hotta A, Yano Y, Iyomasa Y. [Concentration of sulbenicillin in human serum and myocardial tissue]. Jpn J Antibiot. 1982 Jul;35(7):1716-21. Japanese. PubMed PMID: 7176071. 8: Tsuchiya K, Kondo M. Comparative in vitro activities of SCE-129, sulbenicillin, gentamicin, and dibekacin against Pseudomonas. Antimicrob Agents Chemother. 1978 Mar;13(3):536-9. PubMed PMID: 122528; PubMed Central PMCID: PMC352277. 9: Macchioni PL, Del Din G, Filippi G, Baricchi R, Bertani A, Portioli I. Clinical assessment of sulbenicillin in acute respiratory tract infection. Drugs Exp Clin Res. 1985;11(12):879-83. PubMed PMID: 3836118. 10: Ginesu F, Ortu AR, Schena GP, Casali L, Cabiddu R, Ticca MA, Foddai GA, Cardia P, Ligia GP, Torrazza PL, et al. Multicentre clinical and bacteriological study of sulbenicillin in patients with bronchopulmonary infection. Drugs Exp Clin Res. 1985;11(12):885-93. PubMed PMID: 3915276. 11: Gava R. [Sulbenicillin]. G Clin Med. 1988 Dec;69(12):789-92. Review. Italian. PubMed PMID: 3149598. 12: Saccarola L, Crisafi V, Cannizzaro G, Calvo MV, Pesce L, Macaluso S. Results of treatment with sodium sulbenicillin in thirty elderly patients with acute bronchopulmonary infection. Drugs Exp Clin Res. 1985;11(12):895-7. PubMed PMID: 3836119. 13: Haginaka J, Wakai J. High-performance liquid chromatographic assay of carbenicillin, ticarcillin and sulbenicillin in serum and urine using pre-column reaction with 1,2,4-triazole and mercury(II) chloride. Analyst. 1985 Oct;110(10):1185-8. PubMed PMID: 4083496. 14: Fraschini F, Scaglione F, Bichisao E, Marchi E, Scarpazza G, Scarpazza P, Gaffuri Riva V. Comparison between sulbenicillin and piperacillin levels in serum and in bronchial secretions--a pharmacokinetic study. Int J Clin Pharmacol Ther Toxicol. 1987 Nov;25(11):638-42. PubMed PMID: 3429068. 15: Ker CG, Peng CF, Huang TJ, Sheen PC. Antibiotic concentration in bile from patients with obstructive jaundice. II: in vivo and in vitro studies of prednisolone effect on sulbenicillin excretion in bile. Taiwan Yi Xue Hui Za Zhi. 1981 Dec;80(12):1268-74. PubMed PMID: 6951920. 16: Kondo M, Tsuchiya K. Comparative in vivo activities of cefsulodin, sulbenicillin, and gentamicin against Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1978 Jul;14(1):151-3. PubMed PMID: 249623; PubMed Central PMCID: PMC352419. 17: Itoh T, Watanabe N, Ishida M, Tsuda Y, Koyano S, Tsunoi T, Shimada H, Yamada H. Stereoselective disposition of sulbenicillin in humans. Antimicrob Agents Chemother. 1998 Feb;42(2):325-31. PubMed PMID: 9527780; PubMed Central PMCID: PMC105408. 18: Kato Y, Saito A, Yajima O, Tomizawa M, Nakayma I. [Studies on the intravenous administration of sulbenicillin (author's transl)]. Jpn J Antibiot. 1976 Apr;29(4):358-65. Japanese. PubMed PMID: 778428. 19: Miyakawa I, Taniyama K, Inoue H, Lee HC, Mori N. Placental transfer of disodium sulbenicillin. Antimicrob Agents Chemother. 1982 May;21(5):838-9. PubMed PMID: 6808913; PubMed Central PMCID: PMC182022. 20: Kawada Y, Shimizu Y, Nishiura T. Comparative studies of cefotaxime and sulbenicillin in complicated urinary tract infections. J Antimicrob Chemother. 1980 Sep;6 Suppl A:213-8. PubMed PMID: 6252159.