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MedKoo Cat#: 329477 | Name: Sultamicillin
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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
Sultamicillin
CAS#76497-13-7 (free)

Theoretical Analysis

MedKoo Cat#: 329477

Name: Sultamicillin

CAS#: 76497-13-7 (free)

Chemical Formula: C25H30N4O9S2

Exact Mass: 594.1454

Molecular Weight: 594.65

Elemental Analysis: C, 50.50; H, 5.09; N, 9.42; O, 24.21; S, 10.78

Price and Availability

Size Price Availability Quantity
25mg USD 285.00
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Related CAS #
76203-99-1 (HCl) 76497-13-7 (free) 83105-70-8 (tosylate)
Synonym
Sultamicillin; CP-49,952; CP 49,952; CP49,952; CP-49952; CP 49952; CP49952. VD 1827
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
InChi Key
OPYGFNJSCUDTBT-PMLPCWDUSA-N
InChi Code
InChI=1S/C25H30N4O9S2/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/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S([C@]1([H])C2)(=O)=O)N1C2=O)OCOC([C@@H](C(C)(C)S[C@]3([H])[C@@H]4NC([C@H](N)C5=CC=CC=C5)=O)N3C4=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

Preparing Stock Solutions

The following data is based on the product molecular weight 594.65 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
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Baumannii by the broth disk elution test. Eur J Clin Microbiol Infect Dis. 2024 Sep;43(9):1711-1719. doi: 10.1007/s10096-024-04889-6. Epub 2024 Jul 6. PMID: 38970691. 4: Shoulders BR, Santevecchi BA, Venugopalan V, Alexander KM. Ampicillin- Sulbactam for Carbapenem-Susceptible Acinetobacter baumannii Pneumonia: A Case for High-Dose, Continuous Infusion Dosing Strategy in the Trauma ICU. Surg Infect (Larchmt). 2024 Sep;25(7):553-557. doi: 10.1089/sur.2024.135. Epub 2024 Jul 3. PMID: 38958001. 5: Russo A, Gullì SP, D'Avino A, Borrazzo C, Carannante N, Dezza FC, Covino S, Polistina G, Fiorentino G, Trecarichi EM, Mastroianni CM, Torti C, Oliva A. Intravenous fosfomycin for treatment of severe infections caused by carbapenem- resistant Acinetobacter baumannii: A multi-centre clinical experience. Int J Antimicrob Agents. 2024 Jul;64(1):107190. doi: 10.1016/j.ijantimicag.2024.107190. Epub 2024 Apr 30. PMID: 38697579. 6: Zhang Q, Wang P, Shen M, Shan C. Clinical characteristics and risk factors for Klebsiella pneumoniae bloodstream infection in 152 immunocompetent patients. J Infect Dev Ctries. 2024 Feb 29;18(2):219-226. doi: 10.3855/jidc.18204. PMID: 38484340. 7: Matsubayashi Y, Mizuno K, Yamashita T, Asai K. A Case of Thoracic Empyema Caused by Actinomyces naeslundii. Am J Case Rep. 2024 Feb 18;25:e943030. doi: 10.12659/AJCR.943030. PMID: 38368503; PMCID: PMC10883391. 8: Wiesner A, Zagrodzki P, Paśko P. Do dietary interventions exert clinically important effects on the bioavailability of β-lactam antibiotics? A systematic review with meta-analyses. J Antimicrob Chemother. 2024 Apr 2;79(4):722-757. doi: 10.1093/jac/dkae028. PMID: 38334389. 9: Chmelař D, Rozložník M, Hájek M, Pospíšilová N, Kuzma J. Effect of hyperbaric oxygen on the growth and susceptibility of facultatively anaerobic bacteria and bacteria with oxidative metabolism to selected antibiotics. Folia Microbiol (Praha). 2024 Feb;69(1):101-108. doi: 10.1007/s12223-023-01120-5. Epub 2023 Dec 15. PMID: 38100018; PMCID: PMC10876729. 10: Hirano Y, Konishi T, Kaneko H, Itoh H, Matsuda S, Kawakubo H, Uda K, Matsui H, Fushimi K, Daiko H, Itano O, Yasunaga H, Kitagawa Y. Antimicrobial Prophylaxis With Ampicillin-sulbactam Compared With Cefazolin for Esophagectomy: Nationwide Inpatient Database Study in Japan. Ann Surg. 2024 Apr 1;279(4):640-647. doi: 10.1097/SLA.0000000000006182. Epub 2023 Dec 15. PMID: 38099477. 11: Straub A, Utz C, Stapf M, Vollmer A, Breitenbuecher N, Kübler AC, Brands RC, Hartmann S, Lâm TT. Impact of aminopenicillin administration routes on antimicrobial effects of platelet-rich fibrin: An in-vitro investigation. J Stomatol Oral Maxillofac Surg. 2024 Jun;125(3):101725. doi: 10.1016/j.jormas.2023.101725. Epub 2023 Dec 2. PMID: 38048907. 12: Dong YH, Wang JL, Chang CH, Lin JW, Chen YA, Chen CY, Toh S. Association Between Use of Fluoroquinolones and Risk of Mitral or Aortic Valve Regurgitation: A Nationwide Cohort Study. Clin Pharmacol Ther. 2024 Jan;115(1):147-157. doi: 10.1002/cpt.3084. Epub 2023 Nov 13. PMID: 37926942. 13: Shi X, Wu Y, Ni H, Guo M, Cheng Q, Xu Y. Efficacy and Safety of Different Antibiotic Therapies for Bone and Joint Infections: A Network Meta-analysis of Randomized Controlled Trials. Curr Pharm Des. 2023;29(29):2313-2322. doi: 10.2174/0113816128236536231010051130. PMID: 37861039. 14: Kim C, Choi YH, Choi JY, Choi HJ, Park RW, Rhie SJ. Translation of Machine Learning-Based Prediction Algorithms to Personalised Empiric Antibiotic Selection: A Population-Based Cohort Study. Int J Antimicrob Agents. 2023 Nov;62(5):106966. doi: 10.1016/j.ijantimicag.2023.106966. Epub 2023 Sep 15. Erratum in: Int J Antimicrob Agents. 2024 Jun;63(6):107174. doi: 10.1016/j.ijantimicag.2024.107174. PMID: 37716574. 15: Zha S, Niu J, He Z, Fu W, Huang Q, Guan L, Zhou L, Chen R. Prophylactic antibiotics for preventing ventilator-associated pneumonia: a pairwise and Bayesian network meta-analysis. Eur J Med Res. 2023 Sep 15;28(1):348. doi: 10.1186/s40001-023-01323-z. PMID: 37715208; PMCID: PMC10503075. 16: Straub A, Utz C, Stapf M, Vollmer A, Kasper S, Kübler AC, Brands RC, Hartmann S, Lâm TT. Investigation of three common centrifugation protocols for platelet-rich fibrin (PRF) as a bio-carrier for ampicillin/sulbactam: a prospective trial. Clin Oral Investig. 2023 Oct;27(10):5991-5998. doi: 10.1007/s00784-023-05212-x. Epub 2023 Aug 21. PMID: 37603167; PMCID: PMC10560174. 17: Tunay H, Tun AA, Boyac EO, Kesli R, Demırturk N. Evaluation of active microorganisms and antibiotic susceptibility in community-acquired intraabdominal infections in children. Ann Ital Chir. 2023;94:289-294. PMID: 37530061. 18: Wang CH, Huang ML, Zhuo ZQ, Wang ZX, Chen L, Song YQ, Yu H. [Clinical features and antimicrobial resistance of invasive non-typhoid Salmonella infection in children at Xiamen]. Zhonghua Er Ke Za Zhi. 2023 Aug 2;61(8):685-689. Chinese. doi: 10.3760/cma.j.cn112140-20230227-00135. PMID: 37528007. 19: Hu Y, Yan A, Jiang F. Effect of Clindamycin compared with Ampicillin- Sulbactam as prophylactic antibiotics for wound infections following major surgery for head and neck cancer: A meta-analysis. Int Wound J. 2023 Dec;20(10):4151-4158. doi: 10.1111/iwj.14312. Epub 2023 Jul 22. PMID: 37483017; PMCID: PMC10681415. 20: Tobudic S, Bahrs C, Schneider L, Paulussen E, Bartonickova L, Hagel S, Starzengruber P, Burgmann H, Pletz MW. Early treatment response to piperacillin/tazobactam in patients with bloodstream infections caused by non- ESBL ampicillin/sulbactam-resistant Escherichia coli: a binational cohort study. Infection. 2023 Dec;51(6):1749-1758. doi: 10.1007/s15010-023-02074-z. Epub 2023 Jul 18. PMID: 37462895; PMCID: PMC10665230.