Benzylpenicillin

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

MedKoo CAT#: 571333

CAS#: 61-33-6

Description: Benzylpenicillin is a penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on gamma-aminobutyric acid mediated synaptic transmission.


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Benzylpenicillin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571333
Name: Benzylpenicillin
CAS#: 61-33-6
Chemical Formula: C16H18N2O4S
Exact Mass: 334.0987
Molecular Weight: 334.4
Elemental Analysis: C, 57.47; H, 5.43; N, 8.38; O, 19.14; S, 9.59


Synonym: Benzylpenicillin; Galofak; Cilopen; Pradupen

IUPAC/Chemical Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

InChi Key: JGSARLDLIJGVTE-MBNYWOFBSA-N

InChi Code: InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

SMILES Code: O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(CC3=CC=CC=C3)=O)N1C2=O)O


Technical Data

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).

Harmonized System Code:
293490


References

1: Jain R, Bork O, Tucker IG. Stability of penethamate, a benzylpenicillin ester prodrug, in oily vehicles. Drug Dev Ind Pharm. 2015;41(11):1801-8. doi: 10.3109/03639045.2015.1009091. Epub 2015 Feb 12. PubMed PMID: 25673045.

2: Olsén L, Bremer H, Olofsson K, Bröjer J, Bondesson U, Bergh A, Nostell K, Broström H, Bengtsson B, Ingvast-Larsson C. Intramuscular administration of sodium benzylpenicillin in horses as an alternative to procaine benzylpenicillin. Res Vet Sci. 2013 Aug;95(1):212-8. doi: 10.1016/j.rvsc.2013.01.019. Epub 2013 Feb 15. PubMed PMID: 23419937.

3: Lacombe-Barrios J, Salas M, Gómez F, Doña I, Ariza A, Mayorga C, Blanca M, Montañez MI, Torres MJ. The Addition of Benzylpenicillin Does Not Increase the Skin Test Sensitivity Obtained With Classic β-Lactam Determinants. J Investig Allergol Clin Immunol. 2016;26(1):52-4. PubMed PMID: 27012018.

4: Jekl V, Hauptman K, Minarikova A, Kohutova S, Knotek Z, Gajdziok J, Muselik J, Sedlak L, Vetchy D. Pharmacokinetic study of benzylpenicillin potassium after intramuscular administration in rabbits. Vet Rec. 2016 Jul 2;179(1):18. doi: 10.1136/vr.103531. Epub 2016 May 31. PubMed PMID: 27246817.

5: Aldeek F, Rosana MR, Hamilton ZK, Crosswhite MR, Burrows CW, Singh S, Gerard G, Hammack W, Cook JM. LC-MS/MS Method for the Determination and Quantitation of Penicillin G and Its Metabolites in Citrus Fruits Affected by Huanglongbing. J Agric Food Chem. 2015 Jul 8;63(26):5993-6000. doi: 10.1021/acs.jafc.5b02030. Epub 2015 Jun 23. PubMed PMID: 26072945.

6: Deng S, Ma X, Su E, Wei D. Efficient cascade synthesis of ampicillin from penicillin G potassium salt using wild and mutant penicillin G acylase from Alcaligenes faecalis. J Biotechnol. 2016 Feb 10;219:142-8. doi: 10.1016/j.jbiotec.2015.12.034. Epub 2015 Dec 28. PubMed PMID: 26732414.

7: Aldeek F, Canzani D, Standland M, Crosswhite MR, Hammack W, Gerard G, Cook JM. Identification of Penicillin G Metabolites under Various Environmental Conditions Using UHPLC-MS/MS. J Agric Food Chem. 2016 Aug 10;64(31):6100-7. doi: 10.1021/acs.jafc.5b06150. Epub 2016 Mar 7. PubMed PMID: 26906275.

8: Nieto JE, Trela J, Stanley SD, Yamout S, Snyder JR. Pharmacokinetics of a combination of amikacin sulfate and penicillin G sodium for intravenous regional limb perfusion in adult horses. Can J Vet Res. 2016 Jul;80(3):230-5. PubMed PMID: 27408337; PubMed Central PMCID: PMC4924558.

9: Amarilyo G, Glatstein M, Alper A, Scolnik D, Lavie M, Schneebaum N, Grisaru-Soen G, Assia A, Ben-Sira L, Reif S. IV Penicillin G is as effective as IV cefuroxime in treating community-acquired pneumonia in children. Am J Ther. 2014 Mar-Apr;21(2):81-4. doi: 10.1097/MJT.0b013e3182459c28. PubMed PMID: 22407197.

10: Neely M, Kaplan EL, Blumer JL, Faix DJ, Broderick MP. A population pharmacokinetic modeling approach shows that serum penicillin G concentrations are below inhibitory concentrations by two weeks after benzathine penicillin G injection in the majority of young adults. Antimicrob Agents Chemother. 2014 Nov;58(11):6735-41. doi: 10.1128/AAC.02744-14. Epub 2014 Sep 2. PubMed PMID: 25182635; PubMed Central PMCID: PMC4249386.

11: Schliamser SE, Bolander H, Kourtopoulos H, Norrby SR. Neurotoxicity of benzylpenicillin: correlation to concentrations in serum, cerebrospinal fluid and brain tissue fluid in rabbits. J Antimicrob Chemother. 1988 Mar;21(3):365-72. PubMed PMID: 3360694.

12: Al-Hadramy MS, Aman H, Omer A, Khan MA. Benzylpenicillin-induced neutropenia. J Antimicrob Chemother. 1986 Feb;17(2):251-3. PubMed PMID: 3700289.

13: Schliamser SE, Bolander H, Kourtopoulos H, Sigaard J, Norrby SR. Neurotoxicity of benzylpenicillin in experimental Escherichia coli meningitis. J Antimicrob Chemother. 1988 Oct;22(4):521-8. PubMed PMID: 3060460.

14: Roets E, Rappe P, Heeren M, Hoebus J, Verbruggen A, Hoogmartens J. Investigation of the reaction mechanism of the mercurimetric determination of benzylpenicillin. J Pharm Biomed Anal. 1996 Jun;14(8-10):1141-9. PubMed PMID: 8818026.

15: Kelsey SM, Wood ME, Shaw E, Jenkins GC, Newland AC. A comparative study of intravenous ciprofloxacin and benzylpenicillin versus netilmicin and piperacillin for the empirical treatment of fever in neutropenic patients. J Antimicrob Chemother. 1990 Jan;25(1):149-57. PubMed PMID: 2180889.

16: Oukessou M. Influence of injection site on the absorption of benzylpenicillin sodium in the dromedary. Zentralbl Veterinarmed A. 1995 Sep;42(7):431-4. PubMed PMID: 8594836.

17: de Haan P, Kalsbeek GL. Humoral immune response to some benzylpenicillin preparations. Allergy. 1983 Jul;38(5):319-24. PubMed PMID: 6412583.

18: Agapitova IV, Iakovlev VP. [Effect of sulfalene and furosemide on benzylpenicillin kinetics in rats with aseptic inflammation]. Antibiot Khimioter. 1988 Dec;33(12):917-21. Russian. PubMed PMID: 3245708.

19: Ingold A. Conversion of benzylpenicillin to penicilloic acid in patients with chronic bronchial infections. Chemotherapy. 1976;22(2):88-96. PubMed PMID: 1253635.

20: Weihrauch TR, Schmidt W, Höffler D, Krieglstein J. The neurotoxic effect of benzylpenicillin and ampicillin studied in the rabbit. Arzneimittelforschung. 1974 Mar;24(3):317-21. PubMed PMID: 4407410.