Penethamate Free Base

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

MedKoo CAT#: 414038

CAS#: 3689-73-4 (free base)

Description: Penethamate Free Base is used in intramammary products for treatment of mastitis in cows and as an injectable solution for treatment of bacterial infections in swine and cattle.

Chemical Structure

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Penethamate Free Base
CAS# 3689-73-4 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 414038
Name: Penethamate Free Base
CAS#: 3689-73-4 (free base)
Chemical Formula: C22H31N3O4S
Exact Mass: 433.20
Molecular Weight: 433.570
Elemental Analysis: C, 60.95; H, 7.21; N, 9.69; O, 14.76; S, 7.39

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 3689-73-4 (free base)   808-71-9 (hydriodide)  

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

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: 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.