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MedKoo Cat#: 318162 | Name: Loracarbef

Description:

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

Loracarbef is an antibiotic. It is a carbacephem, but it is sometimes grouped together with the second-generation cephalosporin antibiotics. Loracarbef is a synthetic "carba" analog of cefaclor, and is more stable chemically. Loracarbef received FDA approval in 1991 and it was marketed under the trade name Lorabid.

Chemical Structure

Loracarbef
Loracarbef
CAS#76470-66-1

Theoretical Analysis

MedKoo Cat#: 318162

Name: Loracarbef

CAS#: 76470-66-1

Chemical Formula: C16H16ClN3O4

Exact Mass: 349.0829

Molecular Weight: 349.77

Elemental Analysis: C, 54.94; H, 4.61; Cl, 10.14; N, 12.01; O, 18.30

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 #
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Synonym
Loracarbef; Lorabid; Lorafem; Loracarbefum; CHEBI:47544; loracarbef monohydrate; Lorafem; Lorax;
IUPAC/Chemical Name
(6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
JAPHQRWPEGVNBT-UTUOFQBUSA-N
InChi Code
InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1
SMILES Code
C1CC(=C(N2[C@H]1[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)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 349.77 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: Balatsouras DG, Korres S, Rallis E, Eliopoulos P, Ferekidis E. Twice-daily dosing of loracarbef 15 mg/kg versus 30 mg/kg in the treatment of children with acute sinusitis. Drugs Exp Clin Res. 2005;31 Suppl:1-5. PubMed PMID: 16444905. 2: Orrling A, Kamme C, Stjernquist-Desatnik A. Penicillin V, loracarbef and clindamycin in tonsillar surface fluid during acute group A streptococcal pharyngotonsillitis. Scand J Infect Dis. 2005;37(6-7):429-35. PubMed PMID: 16012002. 3: Paster RZ, McAdoo MA, Keyserling CH, Nemeth MA, Tack KJ, Griffin TJ. A comparison of a five-day regimen of cefdinir with a seven-day regimen of loracarbef for the treatment of acute exacerbations of chronic bronchitis. Int J Clin Pract. 2000 Jun;54(5):293-9. PubMed PMID: 10954955. 4: Gooch WM 3rd, Adelglass J, Kelsey DK, Masica D, Johns D Jr, Weinberg BC. Loracarbef versus clarithromycin in children with acute otitis media with effusion. Clin Ther. 1999 Apr;21(4):711-22. PubMed PMID: 10363736. 5: Björnsson E, Olsson R. Acute liver injury due to loracarbef. J Hepatol. 1997 Mar;26(3):739-40. PubMed PMID: 9075688. 6: Benn RA, Fernandes CJ, Nimmo GR. A national collaborative study of the in vitro activity of oral cephalosporins and loracarbef (LY 163892). Australian Group for the Study of Antimicrobial Resistance (AGAR). Pathology. 1997 Feb;29(1):79-83. PubMed PMID: 9094185. 7: Roos K, Larsson P. Loracarbef versus phenoxymethylpenicillin in the treatment of recurrent streptococcal pharyngotonsillitis. Scand J Infect Dis. 1997;29(2):141-5. PubMed PMID: 9181649. 8: Shandler L, Gonzales J, Overturf GD. Recurrence of pneumococcal sepsis caused by an intermediately penicillin-resistant organism treated with loracarbef. Pediatr Infect Dis J. 1996 Apr;15(4):379-80. PubMed PMID: 8866813. 9: Stenquist M, Olen L, Jannert M, Näslund L, Zeckel ML. Penetration of loracarbef into the maxillary sinus: a pharmacokinetic assessment. Clin Ther. 1996 Mar-Apr;18(2):273-84. PubMed PMID: 8733988. 10: Thieme RE, Caldwell SA, Lum GM. Acute interstitial nephritis associated with loracarbef therapy. J Pediatr. 1995 Dec;127(6):997-1000. PubMed PMID: 8523206. 11: Zeckel ML, Johns D Jr, Masica DN, Farlow D. Twice-daily dosing of loracarbef 200 mg versus 400 mg in the treatment of patients with acute maxillary sinusitis. Clin Ther. 1995 Mar-Apr;17(2):214-30. PubMed PMID: 7614522. 12: Dantzig AH, Duckworth DC, Tabas LB. Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta. 1994 Apr 20;1191(1):7-13. PubMed PMID: 8155686. 13: Floor M, van Akkeren F, Rozenberg-Arska M, Visser M, Kolsters A, Beumer H, Verhoef J. Effect of loracarbef and amoxicillin on the oropharyngeal and intestinal microflora of patients with bronchitis. Scand J Infect Dis. 1994;26(2):191-7. PubMed PMID: 8036475. 14: Lees AS, Andrews JM, Wise R. The pharmacokinetics, tissue penetration and in-vitro activity of loracarbef, a beta-lactam antibiotic of the carbacephem class. J Antimicrob Chemother. 1993 Dec;32(6):853-9. PubMed PMID: 8144425. 15: Loracarbef versus doxycycline in the treatment of acute bacterial maxillary sinusitis. Scandinavian Study Group. J Antimicrob Chemother. 1993 Jun;31(6):949-61. PubMed PMID: 8360132. 16: Brogden RN, McTavish D. Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May;45(5):716-36. Review. PubMed PMID: 7686466. 17: Shetler T, Bendele A, Buening M, Clemens J, Colbert W, Deldar A, Helton D, McGrath J, Shannon H, Turk J, et al. General pharmacology of loracarbef in animals. Arzneimittelforschung. 1993 Jan;43(1):60-70. PubMed PMID: 8447851. 18: Loracarbef. Med Lett Drugs Ther. 1992 Sep 18;34(879):87-8. PubMed PMID: 1518460. 19: Roller S, Lode H, Stelzer I, Deppermann KM, Boeckh M, Koeppe P. Pharmacokinetics of loracarbef and interaction with acetylcysteine. Eur J Clin Microbiol Infect Dis. 1992 Sep;11(9):851-5. PubMed PMID: 1468429. 20: Hanfling MJ, Hausinger SA, Squires J. Loracarbef vs. cefaclor in pediatric skin and skin structure infections. Pediatr Infect Dis J. 1992 Aug;11(8 Suppl):S27-30. PubMed PMID: 1513609.