Synonym
Penethamate Free Base; BRN0062929; BRN-0062929; BRN 0062929
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-, 2-(diethylamino)ethyl ester
InChi Key
AFKRZUUZFWTBCC-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H31N3O4S/c1-5-24(6-2)12-13-29-21(28)18-22(3,4)30-20-17(19(27)25(18)20)23-16(26)14-15-10-8-7-9-11-15/h7-11,17-18,20H,5-6,12-14H2,1-4H3,(H,23,26)
SMILES Code
O=C(C(C(C)(C)SC1C2NC(CC3=CC=CC=C3)=O)N1C2=O)OCCN(CC)CC
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
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
433.57
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 |
1: Tucker IG, Jain R, Alawi F, Nanjan K, Bork O. Translational studies on a ready-to-use intramuscular injection of penethamate for bovine mastitis. Drug Deliv Transl Res. 2018 Apr;8(2):317-328. doi: 10.1007/s13346-017-0388-1. PMID: 28512690.
2: 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. PMID: 25673045.
3: McDougall S, Agnew KE, Cursons R, Hou XX, Compton CR. Parenteral treatment of clinical mastitis with tylosin base or penethamate hydriodide in dairy cattle. J Dairy Sci. 2007 Feb;90(2):779-89. doi: 10.3168/jds.S0022-0302(07)71562-X. PMID: 17235155.
4: Salat O, Sérieys F, Poutrel B, Durel L, Goby L. Systemic treatment of subclinical mastitis in lactating cows with penethamate hydriodide. J Dairy Sci. 2008 Feb;91(2):632-40. doi: 10.3168/jds.2007-0174. PMID: 18218750.
5: Almeida RA, Patel D, Friton GM, Oliver SP. Intracellular killing of mastitis pathogens by penethamate hydriodide following internalization into mammary epithelial cells. J Vet Pharmacol Ther. 2007 Apr;30(2):151-6. doi: 10.1111/j.1365-2885.2007.00830.x. PMID: 17348901.
6: Steele N, McDougall S. Effect of prolonged duration therapy of subclinical mastitis in lactating dairy cows using penethamate hydriodide. N Z Vet J. 2014 Jan;62(1):38-46. doi: 10.1080/00480169.2013.830350. Epub 2013 Sep 20. PMID: 24053165.
7: St Rose SG, Swinkels JM, Kremer WD, Kruitwagen CL, Zadoks RN. Effect of penethamate hydriodide treatment on bacteriological cure, somatic cell count and milk production of cows and quarters with chronic subclinical Streptococcus uberis or Streptococcus dysgalactiae infection. J Dairy Res. 2003 Nov;70(4):387-94. doi: 10.1017/s0022029903006460. PMID: 14649409.
8: SOBEK V, HAVA M, NECINA J. K MECHANISMU PUSOBEN'I PENETHAMATU HYDROJODIDU (PENESTERU) [ON THE MECHANISM OF ACTION OF PENETHAMATE HYDROIODIDE (PENESTER)]. Acta Univ Carol Med (Praha). 1963;9:665-72. Czech. PMID: 14167157.
9: RASMUSSEN F. Mammary excretion of benzylpenicillin, erythromycin, and penethamate hydroiodide. Acta Pharmacol Toxicol (Copenh). 1959;16:194-200. doi: 10.1111/j.1600-0773.1959.tb01201.x. PMID: 14436357.
10: Passchyn P, Piepers S, De Vliegher S. Systemic prepartum treatment of end- term dairy heifers with penethamate hydriodide: effect on udder health, milk yield, and culling until 120 days in milk. J Dairy Sci. 2013 Oct;96(10):6324-35. doi: 10.3168/jds.2013-6626. Epub 2013 Aug 9. PMID: 23932138.
