MedKoo Cat#: 317306 | Name: Bacampicillin hydrochloride

Description:

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

Bacampicillin Hydrochloride is the hydrochloride salt of bacampicillin, a prodrug of ampicillin, a broad-spectrum, semisynthetic, beta-lactam aminopenicillin antibiotic with bactericidal activity. Bacampicillin is hydrolyzed in vivo by esterases to its active metabolite ampicillin. Ampicillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall.

Chemical Structure

Bacampicillin hydrochloride
Bacampicillin hydrochloride
CAS#37661-08-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 317306

Name: Bacampicillin hydrochloride

CAS#: 37661-08-8 (HCl)

Chemical Formula: C21H28ClN3O7S

Exact Mass:

Molecular Weight: 501.98

Elemental Analysis: C, 50.25; H, 5.62; Cl, 7.06; N, 8.37; O, 22.31; S, 6.39

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
37661-08-8 (HCl) 50972-17-3 (free base)
Synonym
Bacampicillin hydrochloride; Bacampicillin HCl; Spectrobid; Ambaxin; BAPC; Velbacil; Ambacamp
IUPAC/Chemical Name
1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride
InChi Key
IWVTXAGTHUECPN-ANBBSHPLSA-N
InChi Code
InChI=1S/C21H27N3O7S.ClH/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12;/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25);1H/t11?,13-,14-,15+,18-;/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)OC(OC(OCC)=O)C.[H]Cl
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, not in water
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 501.98 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: Buonomo A, Nucera E, De Pasquale T, Pecora V, Lombardo C, Sabato V, Colagiovanni A, Rizzi A, Aruanno A, Pascolini L, Patriarca G, Schiavino D. Tolerability of aztreonam in patients with cell-mediated allergy to β-lactams. Int Arch Allergy Immunol. 2011;155(2):155-9. doi: 10.1159/000318844. Epub 2010 Dec 22. PubMed PMID: 21196760. 2: Oda M, Fujimoto K, Kobayashi M, Saitoh H. Bacampicillin uptake is shared with thiamine in Caco-2 cells. Biol Pharm Bull. 2007 Jul;30(7):1344-9. PubMed PMID: 17603179. 3: Tucci E, Della Rocca C, Santilli F. Localized bacillary angiomatosis in the oral cavity: observations about a neoplasm with atypical behavior. Description of a case and review of the literature. Minerva Stomatol. 2006 Jan-Feb;55(1-2):67-75. English, Italian. PubMed PMID: 16495874. 4: Béchade D, Desramé J, Raynaud JJ, Algayres JP. [Oesophageal ulcer associated with the use of bacampicillin]. Presse Med. 2005 Feb 26;34(4):299-300. French. PubMed PMID: 15798551. 5: Uchida T, Tanigake A, Miyanaga Y, Matsuyama K, Kunitomo M, Kobayashi Y, Ikezaki H, Taniguchi A. Evaluation of the bitterness of antibiotics using a taste sensor. J Pharm Pharmacol. 2003 Nov;55(11):1479-85. PubMed PMID: 14713358. 6: Heinisch L, Wittmann S, Stoiber T, Scherlitz-Hofmann I, Ankel-Fuchs D, Möllmann U. Synthesis and biological activity of tris- and tetrakiscatecholate siderophores based on poly-aza alkanoic acids or alkylbenzoic acids and their conjugates with beta-lactam antibiotics. Arzneimittelforschung. 2003;53(3):188-95. PubMed PMID: 12705174. 7: Liccardi G, Gilder J, D'Amato M, D'Amato G. Drug allergy transmitted by passionate kissing. Lancet. 2002 May 11;359(9318):1700. PubMed PMID: 12020564. 8: Laurent J, Mégraud F, Fléjou JF, Caekaert A, Barthélemy P. A randomized comparison of four omeprazole-based triple therapy regimens for the eradication of Helicobacter pylori in patients with non-ulcer dyspepsia. Aliment Pharmacol Ther. 2001 Nov;15(11):1787-93. PubMed PMID: 11683693. 9: Takagi K, Iwasaki H, Kishi S, Nakamura T, Takada N, Ueda T. [Murine typhus infected in Oku-etsu area, Fukui Prefecture]. Kansenshogaku Zasshi. 2001 Apr;75(4):341-4. Japanese. PubMed PMID: 11357325. 10: Høiby N. Ecological antibiotic policy. J Antimicrob Chemother. 2000 Sep;46 Suppl 1:59-62; discussion 63-5. PubMed PMID: 11051626. 11: Cederbrant K, Marcusson-Stâhl M, Hultman P. Characterization of primary recall in vitro lymphocyte responses to bacampicillin in allergic subjects. Clin Exp Allergy. 2000 Oct;30(10):1450-9. PubMed PMID: 10998023. 12: Høiby N. Ecological antibiotic policy. J Antimicrob Chemother. 2000 Aug;46 Suppl A:59-62. PubMed PMID: 10969054. 13: Samskog J, Wetterhall M, Jacobsson S, Markides K. Optimization of capillary electrophoresis conditions for coupling to a mass spectrometer via a sheathless interface. J Mass Spectrom. 2000 Jul;35(7):919-24. PubMed PMID: 10934447. 14: Wright AJ. The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. Review. Erratum in: Mayo Clin Proc 1999 Nov;74(11):1184. PubMed PMID: 10090000. 15: Cederbrant K, Stejskal V, Broman P, Lindkvist L, Sundell K. In vitro lymphocyte proliferation in the diagnosis of allergy to phenoxymethylpenicillin. Allergy. 1998 Dec;53(12):1155-61. PubMed PMID: 9930591. 16: Isogai Z, Sunohara A, Tsuji T. Pustular drug eruption due to bacampicilin hydrochloride in a patient with psoriasis. J Dermatol. 1998 Sep;25(9):612-5. PubMed PMID: 9798349. 17: Płotkowiak Z, Popielarz-Brzezińska M, Karolewska J, Mikołajczak A. Study of bacampicillin hydrochloride durability in tablets. Pharmazie. 1998 Sep;53(9):645-6. PubMed PMID: 9770215. 18: Lisi P, Lapomarda V, Stingeni L, Assalve D, Hansel K, Caraffini S, Agostinelli D. Skin tests in the diagnosis of eruptions caused by betalactams. Contact Dermatitis. 1997 Oct;37(4):151-4. PubMed PMID: 9385509. 19: Romano A, Torres MJ, Fernandez J, Vega JM, Mayorga C, Garcia J, Blanca M. Allergic reactions to ampicillin. Studies on the specificity and selectivity in subjects with immediate reactions. Clin Exp Allergy. 1997 Dec;27(12):1425-31. PubMed PMID: 9433938. 20: Ensink JM, Vulto AG, van Miert AS, Tukker JJ, Winkel MB, Fluitman MA. Oral bioavailability and in vitro stability of pivampicillin, bacampicillin, talampicillin, and ampicillin in horses. Am J Vet Res. 1996 Jul;57(7):1021-4. PubMed PMID: 8807014.