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MedKoo Cat#: 540018 | Name: Ampicillin Trihydrate
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Description:

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

Ampicillin Trihydrate is a transpeptidase inhibitor that prevents bacterial cell wall formation. It is effective against gram negative and gram positive bacteria.

Chemical Structure

Ampicillin Trihydrate
Ampicillin Trihydrate
CAS#7177-48-2 (trihydrate)

Theoretical Analysis

MedKoo Cat#: 540018

Name: Ampicillin Trihydrate

CAS#: 7177-48-2 (trihydrate)

Chemical Formula: C16H25N3O7S

Exact Mass: 403.1413

Molecular Weight: 403.45

Elemental Analysis: C, 47.63; H, 6.25; N, 10.42; O, 27.76; S, 7.95

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
69-53-4 (free acid) 33276-75-4 (benzathine) 119229-01-5 (embonate) 7490-86-0 (hemisulfate) 40688-84-4 (HCl) 23277-71-6 (potassium) 69-52-3 (sodium) 7177-48-2 (trihydrate) 114977-84-3 (trimer trisodium)
Synonym
Amcill; Aminobenzyl Penicillin; KS-R1; KS R1; KSR1; Omnipen; Pentrexyl; Polycillin; Ukapen
IUPAC/Chemical Name
(2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
InChi Key
RXDALBZNGVATNY-CWLIKTDRSA-N
InChi Code
InChI=1S/C16H19N3O4S.3H2O/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;;;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);3*1H2/t9-,10-,11+,14-;;;/m1.../s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC([C@H](N)C3=CC=CC=C3)=O)N1C2=O)O.[H]O[H].[H]O[H].[H]O[H]
Appearance
White to light yellow 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

Preparing Stock Solutions

The following data is based on the product molecular weight 403.45 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
1: Credille BC, Giguère S, Vickroy TW, Fishman HJ, Jones AL, Mason ME, DiPietro RO, Ensley DT. Disposition of ampicillin trihydrate in plasma, uterine tissue, lochial fluid, and milk of postpartum dairy cattle. J Vet Pharmacol Ther. 2015 Aug;38(4):330-5. doi: 10.1111/jvp.12178. Epub 2014 Nov 5. PubMed PMID: 25376083. 2: Lima FS, Vieira-Neto A, Vasconcellos GS, Mingoti RD, Karakaya E, Solé E, Bisinotto RS, Martinez N, Risco CA, Galvão KN, Santos JE. Efficacy of ampicillin trihydrate or ceftiofur hydrochloride for treatment of metritis and subsequent fertility in dairy cows. J Dairy Sci. 2014 Sep;97(9):5401-14. doi: 10.3168/jds.2013-7569. Epub 2014 Jun 18. PubMed PMID: 24952780. 3: McNamee JP, Bellier PV. Use of a standardized JaCVAM in vivo rat comet assay protocol to assess the genotoxicity of three coded test compounds; ampicillin trihydrate, 1,2-dimethylhydrazine dihydrochloride, and N-nitrosodimethylamine. Mutat Res Genet Toxicol Environ Mutagen. 2015 Jul;786-788:158-64. doi: 10.1016/j.mrgentox.2015.02.005. Epub 2015 Feb 26. PubMed PMID: 26212307. 4: Baraldi C, Tinti A, Ottani S, Gamberini MC. Characterization of polymorphic ampicillin forms. J Pharm Biomed Anal. 2014 Nov;100:329-40. doi: 10.1016/j.jpba.2014.08.021. Epub 2014 Aug 26. PubMed PMID: 25194347. 5: Ensink JM, Moi A, Vulto AG, Tukker JJ. Bioavailability of pivampicillin and ampicillin trihydrate administered as an oral paste in horses. Vet Q. 1996;18 Suppl 2:S117-20. PubMed PMID: 8933688. 6: Gehring R, van der Merwe D, Pierce AN, Baynes RE, Craigmill AL, Riviere JE. Multivariate meta-analysis of pharmacokinetic studies of ampicillin trihydrate in cattle. Am J Vet Res. 2005 Jan;66(1):108-12. PubMed PMID: 15691044. 7: Dunnick JK, Eustis SL, Huff JE, Haseman JK. Two-year toxicity and carcinogenicity studies of ampicillin trihydrate and penicillin VK in rodents. Fundam Appl Toxicol. 1989 Feb;12(2):252-7. PubMed PMID: 2497039. 8: Brittain HG. Solid-state fluorescence of the trihydrate phases of ampicillin and amoxicillin. AAPS PharmSciTech. 2005 Oct 22;6(3):E444-8. PubMed PMID: 16354003; PubMed Central PMCID: PMC2750389. 9: Sylvestri MF, Makoid MC. Stability of ampicillin trihydrate suspension in amber plastic oral syringes. Am J Hosp Pharm. 1986 Jun;43(6):1496-8. PubMed PMID: 3728487. 10: Ertan M, Tayhan AB, Yulug N. Synthesis and antimicrobial activities of some new tetrahydro-2H-1,3,5-thiadiazine-2-thione derivatives of ampicillin. Arch Pharm (Weinheim). 1990 Sep;323(9):605-9. PubMed PMID: 2288482. 11: Traver DS, Riviere JE. Ampicillin in mares: a comparison of intramuscular sodium ampicillin or sodium ampicillin-ampicillin trihydrate injection. Am J Vet Res. 1982 Mar;43(3):402-4. PubMed PMID: 7073056. 12: Doluisio JT, LaPiana JC, Dittert LW. Pharmacokinetics of ampicillin trihydrate, sodium ampicillin, and sodium dicloxacillin following intramuscular injection. J Pharm Sci. 1971 May;60(5):715-9. PubMed PMID: 5125769. 13: Wise R. Substituted ampicillins. J Antimicrob Chemother. 1977 Jul;3(4):289-90. PubMed PMID: 893236. 14: Brown MP, Stover SM, Kelly RH, Farver TB. Body fluid concentrations of ampicillin trihydrate in 6 horses after a single intramuscular dose. Equine Vet J. 1982 Jan;14(1):83-5. PubMed PMID: 7084185. 15: Kaptsov VA, Karpenko LZ, Solovarov VP. [Hygienic assessment of protective effects of overalls and individual protective devices used in the production of ampicillin trihydrate and its dosage form, ampicillin sodium salt]. Gig Tr Prof Zabol. 1991;(1):23-5. Russian. PubMed PMID: 2060812. 16: Nojavan S, Ghassempour A, Bashour Y, Darbandi MK, Ahmadi SH. Determination of residual solvents and investigation of their effect on ampicillin trihydrate crystal structure. J Pharm Biomed Anal. 2005 Jan 4;36(5):983-8. PubMed PMID: 15620523. 17: Frański R, Czerniel J, Kowalska M, Frańska M. Electrospray ionization collision-induced dissociation tandem mass spectrometry of amoxicillin and ampicillin and their degradation products. Rapid Commun Mass Spectrom. 2014 Apr 15;28(7):713-22. doi: 10.1002/rcm.6834. PubMed PMID: 24573802. 18: Winther L, Baptiste KE, Friis C. Pharmacokinetics in pulmonary epithelial lining fluid and plasma of ampicillin and pivampicillin administered to horses. Res Vet Sci. 2012 Feb;92(1):111-5. doi: 10.1016/j.rvsc.2010.11.001. Epub 2010 Dec 7. PubMed PMID: 21144541. 19: Hitzenberger G, Jaschek I. Comparative studies on the absorption of ampicillin trihydrate and potassium ampicillin. Int J Clin Pharmacol. 1974 Mar;9(2):114-9. PubMed PMID: 4827555. 20: Elsheikh HA, Osman Intisar AM, Abdullah AS. Pharmacokinetics of ampicillin trihydrate following intravenous administration to water deprived Nubian goats. Res Vet Sci. 1998 Sep-Oct;65(2):111-4. PubMed PMID: 9839887.

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