Synonym
Sulbenicillin disodium; alpha-Sulfobenzylpenicillin disodium; Disodium sulbenicillin; Disodium sulfobenzylpenicillin;
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenyl-2-sulfoacetamido)-, disodium salt
InChi Key
FWRNIJIOFYDBES-UHFFFAOYSA-L
InChi Code
InChI=1S/C16H18N2O7S2.2Na/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);;/q;2*+1/p-2
SMILES Code
O=C(C(C(C)(C)SC1C2NC(C(C3=CC=CC=C3)S(=O)([O-])=O)=O)N1C2=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
>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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
458.41
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: 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.
2: Yoshida H, Higaki Y, Ogawa H, Iguchi H, Watanabe M. [Effect of disodium sulbenicillin (SBPC) for urinary tract infections after retropubic prostatectomy, with special reference to SBPC concentration in human prostatic tissue (author's transl)]. Jpn J Antibiot. 1980 Apr;33(4):522-5. Japanese. PubMed PMID: 7411856.
3: Mochizuki K, Torisaki M, Kawasaki K, Shirao Y, Yamashita Y, Kitano K, Yonemura D. Retinal toxicity of antibiotics: evaluation by electroretinogram. Doc Ophthalmol. 1988 Jun;69(2):195-202. PubMed PMID: 3168722.
4: Hayashi N, Kato S, Morimoto H. Effect of gamma irradiation on disodium alpha-sulfobenzylpenicillin in solid state. Int J Appl Radiat Isot. 1977 Aug;28(8):723-6. PubMed PMID: 892926.
5: Burton G, Best DJ, Dixon RA, Kenyon RF, Lashford AG. Studies on 6 alpha-substituted penicillins. II. Synthesis and structure-activity relationships of 6 beta-(2-aryl-2-sulfoacetamido)-6 alpha-methoxy penicillanic acids. J Antibiot (Tokyo). 1986 Oct;39(10):1419-29. PubMed PMID: 3096924.
6: Kawasaki K, Ohnogi J. Nontoxic concentration of antibiotics for intravitreal use--evaluated by human in-vitro ERG. Doc Ophthalmol. 1988 Dec;70(4):301-8. PubMed PMID: 3251718.
7: Fukuda M, Sasaki K. [Antibiotic ophthalmic solutions evaluated by pharmacokinetic parameters of maximum concentration in the aqueous]. Nippon Ganka Gakkai Zasshi. 2002 Apr;106(4):195-200. Japanese. PubMed PMID: 11979978.
8: Kawasaki K, Ohnogi J, Okayama Y, Yonemura D. Effects of antibiotics on the in vitro ERG of the albino rabbit. Penicillins and cephalosporins antibiotics. Doc Ophthalmol. 1987 May;66(1):75-84. PubMed PMID: 3428073.
9: Burton G, Basker MJ, Bentley PH, Best DJ, Dixon RA, Harrington FP, Kenyon RF, Lashford AG, Taylor AW. Preparation and structure-activity relationships of some 6 alpha-substituted penicillins. J Antibiot (Tokyo). 1985 Jun;38(6):721-39. PubMed PMID: 3926736.
10: Yoshida T, Matsuura S, Mayama M, Kameda Y, Kuwahara S. Moxalactam (6059-S), a novel 1-oxa-beta-lactam with an expanded antibacterial spectrum: laboratory evaluation. Antimicrob Agents Chemother. 1980 Mar;17(3):302-12. PubMed PMID: 6448572; PubMed Central PMCID: PMC283781.
