Synonym
CP-47,904; CP47,904; CP 47,904; CP-47904; CP47904; CP 47904; Sulbactam pivoxil; Pivsulbactam.
IUPAC/Chemical Name
(pivaloyloxy)methyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide
InChi Key
OHPVYKXTRACOSQ-ZJUUUORDSA-N
InChi Code
InChI=1S/C14H21NO7S/c1-13(2,3)12(18)22-7-21-11(17)10-14(4,5)23(19,20)9-6-8(16)15(9)10/h9-10H,6-7H2,1-5H3/t9-,10+/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S([C@]1([H])C2)(=O)=O)N1C2=O)OCOC(C(C)(C)C)=O
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
To be determined
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
Biological target:
Sulbactam is a competitive, irreversible beta-lactamase inhibitor.
In vitro activity:
Sulbactam pre-incubation significantly and dose-dependently prevented neuronal death and decline in cell viability induced by OGD in neuron-astrocyte co-cultures, and upregulated GLT-1 expression in astrocyte cultures endured OGD, suggesting that sulbactam might protect neurons against OGD by up-regulating astrocytic GLT-1 expression. Phosphorylated-p38 MAPK expression in astrocytes was up-regulated after the sulbactam pre-incubation and this up-regulation was moderate in amplitude.
Reference: Front Mol Neurosci. 2018 Aug 15;11:281. https://pubmed.ncbi.nlm.nih.gov/11220688/
In vivo activity:
It was shown that administration of sulbactam protected CA1 hippocampal neurons against ischemic insult accompanied with significantly upregulation in the expressions of phosphorylated-p38 MAPK and GLT-1. The time course analysis showed that sulbactam activated p38 MAPK before the GLT-1 upregulation in either normal or global cerebral ischemic rats.
Reference: Sci Rep. 2020 Nov 26;10(1):20601. https://pubmed.ncbi.nlm.nih.gov/33244020/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
347.38
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 |
Formulation protocol:
1. Qi J, Xian XH, Li L, Zhang M, Hu YY, Zhang JG, Li WB. Sulbactam Protects Hippocampal Neurons Against Oxygen-Glucose Deprivation by Up-Regulating Astrocytic GLT-1 via p38 MAPK Signal Pathway. Front Mol Neurosci. 2018 Aug 15;11:281. doi: 10.3389/fnmol.2018.00281. PMID: 30158854; PMCID: PMC6104165.
2. Nakae T, Saito K, Nakajima A. Effect of sulbactam on anti-pseudomonal activity of beta-lactam antibiotics in cells producing various levels of the MexAB-OprM efflux pump and beta-lactamase. Microbiol Immunol. 2000;44(12):997-1001. doi: 10.1111/j.1348-0421.2000.tb02595.x. PMID: 11220688.
3. VanNatta M, Grier L, Khan MH, Pinargote Cornejo P, Alam M, Moussa SH, Smith JG, Aitken SL, Malek AE. In Vivo Emergence of Pandrug-Resistant Acinetobacter baumannii Strain: Comprehensive Resistance Characterization and Compassionate Use of Sulbactam-Durlobactam. Open Forum Infect Dis. 2023 Oct 6;10(10):ofad504. doi: 10.1093/ofid/ofad504. PMID: 37901122; PMCID: PMC10603586.
4. Xian XH, Gao JX, Qi J, Fan SJ, Zhang M, Li WB. Activation of p38 MAPK participates in the sulbactam-induced cerebral ischemic tolerance mediated by glial glutamate transporter-1 upregulation in rats. Sci Rep. 2020 Nov 26;10(1):20601. doi: 10.1038/s41598-020-77583-0. PMID: 33244020; PMCID: PMC7692545.
In vitro protocol:
1. Qi J, Xian XH, Li L, Zhang M, Hu YY, Zhang JG, Li WB. Sulbactam Protects Hippocampal Neurons Against Oxygen-Glucose Deprivation by Up-Regulating Astrocytic GLT-1 via p38 MAPK Signal Pathway. Front Mol Neurosci. 2018 Aug 15;11:281. doi: 10.3389/fnmol.2018.00281. PMID: 30158854; PMCID: PMC6104165.
2. Nakae T, Saito K, Nakajima A. Effect of sulbactam on anti-pseudomonal activity of beta-lactam antibiotics in cells producing various levels of the MexAB-OprM efflux pump and beta-lactamase. Microbiol Immunol. 2000;44(12):997-1001. doi: 10.1111/j.1348-0421.2000.tb02595.x. PMID: 11220688.
In vivo protocol:
1. VanNatta M, Grier L, Khan MH, Pinargote Cornejo P, Alam M, Moussa SH, Smith JG, Aitken SL, Malek AE. In Vivo Emergence of Pandrug-Resistant Acinetobacter baumannii Strain: Comprehensive Resistance Characterization and Compassionate Use of Sulbactam-Durlobactam. Open Forum Infect Dis. 2023 Oct 6;10(10):ofad504. doi: 10.1093/ofid/ofad504. PMID: 37901122; PMCID: PMC10603586.
2. Xian XH, Gao JX, Qi J, Fan SJ, Zhang M, Li WB. Activation of p38 MAPK participates in the sulbactam-induced cerebral ischemic tolerance mediated by glial glutamate transporter-1 upregulation in rats. Sci Rep. 2020 Nov 26;10(1):20601. doi: 10.1038/s41598-020-77583-0. PMID: 33244020; PMCID: PMC7692545.
1: Changov LS, Vassileva BK, Confino MN, Agapova NN. An efficient method for the synthesis of sulbactam pivoxil. Farmaco. 2000 Feb;55(2):134-5. PubMed PMID: 10782385.
2: Davies BI, Maesen FP, Jevons S, Brouwers J. Combination of sulbactam pivoxyl and bacampicillin in acute exacerbations of chronic bronchitis. J Antimicrob Chemother. 1982 Nov;10(5):445-52. PubMed PMID: 6294045.
3: Pei Q, Yang GP, Li ZJ, Peng XD, Fan JH, Liu ZQ. Simultaneous analysis of amoxicillin and sulbactam in human plasma by HPLC-DAD for assessment of bioequivalence. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jul 1;879(21):2000-4. doi: 10.1016/j.jchromb.2011.05.021. PubMed PMID: 21680260.
4: Abdenur JE, Chamoles NA, Guinle AE, Schenone AB, Fuertes AN. Diagnosis of isovaleric acidaemia by tandem mass spectrometry: false positive result due to pivaloylcarnitine in a newborn screening programme. J Inherit Metab Dis. 1998 Aug;21(6):624-30. PubMed PMID: 9762597.
5: Sjövall J, Huitfeldt B, Magni L, Nord CE. Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. Review. PubMed PMID: 3547627.
6: English AR, Girard D, Jasys VJ, Martingano RJ, Kellogg MS. Orally effective acid prodrugs of the beta-lactamase inhibitor sulbactam. J Med Chem. 1990 Jan;33(1):344-7. PubMed PMID: 2296030.
