Sulbactam free acid | CAS# 68373-14-8 (free acid) | β-lactamase inhibitor

MedKoo Cat#: 526371 | Name: Sulbactam

Description:

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

Sulbactam, also known as CP 45899, is a β-lactamase inhibitor. This drug is given in combination with β-lactam antibiotics to inhibit β-lactamase, an enzyme produced by bacteria that destroys the antibiotics. Sulbactam is an irreversible inhibitor of β-lactamase; it binds to the enzyme and does not allow it to degrade the antibiotic.Sulbactam is able to inhibit the most common forms of β-lactamase but is not able to interact with the AmpC cephalosporinase. Thus, it confers little protection against bacteria such as Pseudomonas aeruginosa, Citrobacter, Enterobacter, and Serratia, which often express this gene.

Chemical Structure

Sulbactam

CAS#68373-14-8 (free acid)

Theoretical Analysis

MedKoo Cat#: 526371

Name: Sulbactam

CAS#: 68373-14-8 (free acid)

Chemical Formula: C8H11NO5S

Exact Mass: 233.0358

Molecular Weight: 233.24

Elemental Analysis: C, 41.20; H, 4.75; N, 6.01; O, 34.30; S, 13.75

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
2g	USD 450.00	2 Weeks
5g	USD 750.00	2 Weeks
10g	USD 1,050.00	2 Weeks
20g	USD 1,650.00	2 Weeks

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Related CAS #

69388-84-7 (sodium) 69388-79-0 (pivoxil) 68373-14-8 (free acid)

Synonym

CP-45899; CP 45899; CP45899; CP-45,899; CP 45,899; CP45,899; Sulbactam

IUPAC/Chemical Name

(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxide

InChi Key

FKENQMMABCRJMK-RITPCOANSA-N

InChi Code

InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

SMILES Code

O=C([C@@H](C(C)(C)S([C@]1([H])C2)(=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

Related CAS# 68373-14-8 (Sulbactam) 69388-84-7 (Sulbactam sodium)

Product Data

Product Data

Instruction

View handling instruction

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 233.24 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:

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: Chu H, Zhao L, Wang M, Liu Y, Gui T, Zhang J. Sulbactam-based therapy for Acinetobacter baumannii infection: a systematic review and meta-analysis. Braz J Infect Dis. 2013 Jul-Aug;17(4):389-94. doi: 10.1016/j.bjid.2012.10.029. Review. PubMed PMID: 23602463. 2: Adnan S, Paterson DL, Lipman J, Roberts JA. Ampicillin/sulbactam: its potential use in treating infections in critically ill patients. Int J Antimicrob Agents. 2013 Nov;42(5):384-9. doi: 10.1016/j.ijantimicag.2013.07.012. Review. PubMed PMID: 24041466. 3: Betrosian AP, Douzinas EE. Ampicillin-sulbactam: an update on the use of parenteral and oral forms in bacterial infections. Expert Opin Drug Metab Toxicol. 2009 Sep;5(9):1099-112. doi: 10.1517/17425250903145251. Review. PubMed PMID: 19621991. 4: Akova M. Sulbactam-containing beta-lactamase inhibitor combinations. Clin Microbiol Infect. 2008 Jan;14 Suppl 1:185-8. Review. Erratum in: Clin Microbiol Infect. 2008 May;14 Suppl 5:21-4. PubMed PMID: 18154545. 5: Lode HM. Rational antibiotic therapy and the position of ampicillin/sulbactam. Int J Antimicrob Agents. 2008 Jul;32(1):10-28. doi: 10.1016/j.ijantimicag.2008.02.004. Review. PubMed PMID: 18539004. 6: Rafailidis PI, Ioannidou EN, Falagas ME. Ampicillin/sulbactam: current status in severe bacterial infections. Drugs. 2007;67(13):1829-49. Review. PubMed PMID: 17722953. 7: Herych ID, Vashchuk VV. [Modern possibilities of hepacef combi (cefoperazon/sulbactam) application for the treatment of surgical infection]. Klin Khir. 2011 Feb;(2):65-9. Review. Ukrainian. PubMed PMID: 21548334. 8: Barcelona L, Marín M, Stamboulian D. [Betalactam antibiotics combined with bectalactamases inhibitors. Amoxicillin-sulbactam]. Medicina (B Aires). 2008;68(1):65-74. Review. Spanish. PubMed PMID: 18416324. 9: Levin AS. Multiresistant Acinetobacter infections: a role for sulbactam combinations in overcoming an emerging worldwide problem. Clin Microbiol Infect. 2002 Mar;8(3):144-53. Review. PubMed PMID: 12010169. 10: Soutric J, Bantar C, Caruso N, Heguilén R, Casellas JM Jr, Casellas JM, Farinati A, Jasovich A, Arenoso H, Rodriguez M. Review of pharmacokinetic, pharmacodynamic and clinical studies with a modern combination of amoxicillin/sulbactam. Chemotherapy. 2006;52(4):200-4. Review. PubMed PMID: 16720984. 11: Kanra G. Experience with ampicillin/sulbactam in severe infections. J Int Med Res. 2002;30 Suppl 1:20A-30A. Review. PubMed PMID: 11921491. 12: 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. 13: Singh GS. Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam. Mini Rev Med Chem. 2004 Jan;4(1):93-109. Review. PubMed PMID: 14754446. 14: 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. 15: Williams JD. beta-Lactamase inhibition and in vitro activity of sulbactam and sulbactam/cefoperazone. Clin Infect Dis. 1997 Mar;24(3):494-7. Review. PubMed PMID: 9114205. 16: Garnacho-Montero J, Amaya-Villar R, Ferrándiz-Millón C, Díaz-Martín A, López-Sánchez JM, Gutiérrez-Pizarraya A. Optimum treatment strategies for carbapenem-resistant Acinetobacter baumannii bacteremia. Expert Rev Anti Infect Ther. 2015 Jun;13(6):769-77. doi: 10.1586/14787210.2015.1032254. Review. PubMed PMID: 25865094. 17: Chapman E, Reveiz L, Illanes E, Bonfill Cosp X. Antibiotic regimens for management of intra-amniotic infection. Cochrane Database Syst Rev. 2014 Dec 19;(12):CD010976. doi: 10.1002/14651858.CD010976.pub2. Review. PubMed PMID: 25526426. 18: Siriwachirachai T, Sangkomkamhang US, Lumbiganon P, Laopaiboon M. Antibiotics for meconium-stained amniotic fluid in labour for preventing maternal and neonatal infections. Cochrane Database Syst Rev. 2014 Nov 6;(11):CD007772. doi: 10.1002/14651858.CD007772.pub3. Review. PubMed PMID: 25374369. 19: Shakil S, Azhar EI, Tabrez S, Kamal MA, Jabir NR, Abuzenadah AM, Damanhouri GA, Alam Q. New Delhi metallo-β-lactamase (NDM-1): an update. J Chemother. 2011 Oct;23(5):263-5. Review. PubMed PMID: 22005056. 20: Alpuche-Aranda CM. Beta-lactamase production and the role of ampicillin/sulbactam. Pediatr Infect Dis J. 1998 Mar;17(3 Suppl):S8-11; discussion S20-1. Review. PubMed PMID: 9519908.