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MedKoo Cat#: 329888 | Name: Sultamicillin tosylate hydrate
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Description:

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

Sultamicillin, also known as CP-49952 and VD 1827, is an oral form of the antibiotic combination (codrug or mutual prodrug) ampicillin/sulbactam. It contains esterified ampicillin and sulbactam and is marketed under a number of trade names,Unasyn from Pfizer. After absorption, sultamicillin releases ampicillin and sulbactam into the system, so all the antibacterial efficacy of sultamicillin is due to ampicillin and sulbactam. Ampicillin exerts antibacterial activity against sensitive organisms by inhibiting biosynthesis of cell wall mucopeptide where as sulbactam irreversibly inhibits most important beta-lactamases that occur in resistant strains.

Chemical Structure

Sultamicillin tosylate hydrate
Sultamicillin tosylate hydrate
CAS#83105-70-8 (tosylate)

Theoretical Analysis

MedKoo Cat#: 329888

Name: Sultamicillin tosylate hydrate

CAS#: 83105-70-8 (tosylate)

Chemical Formula: C32H42N4O14S3

Exact Mass: 0.0000

Molecular Weight: 802.88

Elemental Analysis: C, 47.87; H, 5.27; N, 6.98; O, 27.90; S, 11.98

Price and Availability

Size Price Availability Quantity
250mg USD 385.00
1g USD 1,250.00
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Related CAS #
76203-99-1 (HCl) 76497-13-7 (free) 83105-70-8 (tosylate)
Synonym
Sultamicillin tosilate; Sultamicillin tosylate hydrate; Sultamicillin; CP-49,952; CP 49,952; CP49,952; CP-49952; CP 49952; CP49952. VD 1827; Bacimex; p-Toluenesulfonate Sbtpc; Unacid PD oral; acim orale.
IUPAC/Chemical Name
(((2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl)oxy)methyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide 4-methylbenzenesulfonate dihydrate
InChi Key
KNVDAMRBJYZXRW-ZAKZIJIGSA-N
InChi Code
InChI=1S/C25H30N4O9S2.C7H8O3S.2H2O/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18;1-6-2-4-7(5-3-6)11(8,9)10;;/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31);2-5H,1H3,(H,8,9,10);2*1H2/t14-,15-,16-,17+,18+,21-;;;/m1.../s1
SMILES Code
O=S(C1=CC=C(C)C=C1)(O)=O.O=C([C@@H](C(C)(C)S([C@]2([H])C3)(=O)=O)N2C3=O)OCOC([C@@H](C(C)(C)S[C@]4([H])[C@@H]5NC([C@H](N)C6=CC=CC=C6)=O)N4C5=O)=O.[H]O[H].[H]O[H]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 802.88 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
1: Kumar VJ, Gupta PB, Kumar KS, Ray UK, Sreenivasulu B, Kumar GS, Rao KR, Sharma HK, Mukkanti K. Identification, isolation and characterization of a new degradation product in sultamicillin drug substance. J Pharm Biomed Anal. 2011 Feb 20;54(3):582-7. doi: 10.1016/j.jpba.2010.09.016. PubMed PMID: 20934824. 2: Koytchev R, Ozalp Y, Erenmemisoglu A, Kunter U, Alpan RS. Effect of the formulation on the bioequivalence of sultamicillin: tablets and suspension. Arzneimittelforschung. 2004 Sep;54(9A):634-9. PubMed PMID: 15497673. 3: Sailer R, Arnold P, Erenmemişoğlu A, Martin W, Tamur U, Kanzik I, Hincal AA. Bioequivalence study of sultamicillin suspensions. Arzneimittelforschung. 2007;57(4):232-7. PubMed PMID: 17515294. 4: Topuz B, Katircioğlu O, Bayramoğlu I, Ardiç FN, Erbudak H. Low dose sultamicillin in acute sinusitis. Infez Med. 2002 Mar;10(1):45-8. PubMed PMID: 12700441. 5: Ferreira JB, Rapoport PB, Sakano E, Kós AO, Piltcher OB, Pignatari SS, Pinheiro SD, Mocellin M. Efficacy and safety of Sultamicillin (Ampicillin/Sulbactan) and Amoxicillin/Clavulanic acid in the treatment of upper respiratory tract infections in adults--an open-label, multicentric, randomized trial. Braz J Otorhinolaryngol. 2006 Jan-Feb;72(1):104-11. PubMed PMID: 16917560. 6: Pajchel G, Tyski S. Application of micellar electrokinetic chromatography to the determination of sultamicillin in oral pharmaceutical preparations. J Chromatogr A. 2002 Dec 6;979(1-2):315-21. PubMed PMID: 12498263. 7: Laviana L, Fernández-Marí F, Bayod M, Blanco D. HPLC for in-process control in the production of sultamicillin. J Pharm Biomed Anal. 2003 Feb 26;31(2):321-8. PubMed PMID: 12609671. 8: Dajani A. Use of ampicillin/sulbactam and sultamicillin in pediatric infections: a re-evaluation. J Int Med Res. 2001 Jul-Aug;29(4):257-69. Review. PubMed PMID: 11675898. 9: Lode H. Role of sultamicillin and ampicillin/sulbactam in the treatment of upper and lower bacterial respiratory tract infections. Int J Antimicrob Agents. 2001 Sep;18(3):199-209. Review. PubMed PMID: 11673031. 10: Abdullah B, Lazim NM, Salim R. The effectiveness of Tualang honey in reducing post-tonsillectomy pain. Kulak Burun Bogaz Ihtis Derg. 2015;25(3):137-43. doi: 10.5606/kbbihtisas.2015.00008. PubMed PMID: 26050853. 11: Mat Lazim N, Abdullah B, Salim R. The effect of Tualang honey in enhancing post tonsillectomy healing process. An open labelled prospective clinical trial. Int J Pediatr Otorhinolaryngol. 2013 Apr;77(4):457-61. doi: 10.1016/j.ijporl.2012.11.036. PubMed PMID: 23273638. 12: Moosdeen F. The role of sulbactam-ampicillin/sultamicillin in mixed infections. Int J Antimicrob Agents. 1999 Aug;12 Suppl 1:S1. PubMed PMID: 10526866. 13: Hu CQ, Yang MZ, Zhang DC, Liu W, Wu Q, Liang H, Jin SH. [Studies on sultamicillin hydrolysis]. Yao Xue Xue Bao. 1997 Jul;32(7):553-7. Chinese. PubMed PMID: 11596284. 14: Arredondo-García JL. Use of ampicillin/sulbactam (sultamicillin) in the management of pediatric infections. Introduction. Pediatr Infect Dis J. 1998 Mar;17(3 Suppl):S3. PubMed PMID: 9519906. 15: López EL, Rivas NA. Clinical use of sultamicillin (ampicillin/sulbactam) in children. Pediatr Infect Dis J. 1998 Mar;17(3 Suppl):S12-4; discussion S20-1. PubMed PMID: 9519909. 16: Argekar AP, Kunjir SS. Quantitative estimation of sultamicillin p-toluenesulfonate in pharmaceutical preparations by reverse-phase high performance liquid chromatography. J Pharm Biomed Anal. 1996 Dec;15(3):423-7. PubMed PMID: 8951704. 17: Chan KH, Bluestone CD, Tan LS, Reisinger KS, Blatter MM, Fall PA. Comparative study of sultamicillin and amoxicillin-clavulanate: treatment of acute otitis media. Pediatr Infect Dis J. 1993 Jan;12(1):24-8. PubMed PMID: 8417421. 18: Friedel HA, Campoli-Richards DM, Goa KL. Sultamicillin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1989 Apr;37(4):491-522. Review. Erratum in: Drugs 1989 Nov;38(5):followi. PubMed PMID: 2661196. 19: Hara K, Kobayashi H. Sultamicillin experiences in the field of internal medicine. APMIS Suppl. 1989;5:51-6. PubMed PMID: 2660872. 20: Göker K, Güvener O. Antibacterial effects of ofloxacin, clindamycin and sultamicillin on surgical removal of impacted third molars. J Marmara Univ Dent Fac. 1992 Sep;1(3):237-49. PubMed PMID: 1308784.