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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 460017669 |
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| Verifiedfields = changed |
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| IUPAC_name = (6''R'',7''R'')-3--<br />8-oxo-7--<br />5-thia-1-azabicyclooct-2-ene-<br />2-carboxylic acid |
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| verifiedrevid = 401029431 |
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| image = Nitrocefin.svg |
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| IUPAC_name = (2''S'',5''R'',6''R'')-6-{amino}-<br>3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<br>heptane-2-carboxylic acid |
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| image = Carbenicillin.svg |
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<!--Clinical data--> |
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| tradename = Geocillin |
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| Drugs.com = {{drugs.com|monograph|geocillin}} |
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| pregnancy_US = B |
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| pregnancy_category = Passes into ] |
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| legal_US = Rx-only |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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| bioavailability = 30 to 40% |
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| protein_bound = 30 to 60% |
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| metabolism = Minimal |
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| elimination_half-life = 1 hour |
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| excretion = ] (30 to 40%) |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 4697-36-3 |
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| CAS_number = 41906-86-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ATC_prefix = J01 |
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| UNII = EWP54G0J8F |
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| ATC_suffix = CA03 |
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| PubChem = 6436140 |
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| ATC_supplemental = |
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| PubChem = 20824 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00578 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 19599 |
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| ChemSpiderID = 4940809 |
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| ChEMBL = 480517 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = G42ZU72N5G |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 3393 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1214 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=17 | H=18 | N=2 | O=6 | S=1 |
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| C=21 | H=16 | N=4 | O=8 | S=2 |
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| smiles = O=C(Cc1cccs1)N1C(=O)N2C(C(=O)O)=C(/C=C/c3ccc((=O))cc3(=O))CS12 |
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| molecular_weight = 378.401 g/mol |
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| smiles = O=C(O)2N3C(=O)(NC(=O)C(c1ccccc1)C(=O)O)3SC2(C)C |
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| InChI = 1/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 |
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| InChIKey = FPPNZSSZRUTDAP-UWFZAAFLBI |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 |
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| StdInChI = 1S/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FPPNZSSZRUTDAP-UWFZAAFLSA-N |
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| StdInChIKey = LHNIIDJCEODSHA-OQRUQETBSA-N |
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}} |
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}} |
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'''Carbenicillin''' is a bacteriolytic ] belonging to the ] subgroup of the ]s. It was discovered by scientists at ] and marketed as Pyopen. It has ] coverage which includes '']'' but limited ] coverage. The carboxypenicillins are susceptible to degradation by ] enzymes, although they are more resistant than ] to degradation. Carbenicillin is also more stable at lower pH than ampicillin. |
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{{DISPLAYTITLE:Nitrocefin}} |
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The antibiotic is very soluble in water and is acid-labile. Aqueous solutions are short-lived. Working concentration in the lab: up to 100 µg per ml. |
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'''Nitrocefin''' is a ] ] substrate routinely used to detect the presence of ] enzymes produced by various microbes. ] mediated resistance to ] antibiotics such as ] is a widespread mechanism of resistance for a number of ] including members of the family ], a major group of enteric ]. Other methods for ] detection exist including ]; however, nitrocefin allows for rapid ] detection using few materials and inexpensive equipment.<ref name="O'Callaghan_1972">{{cite journal | vauthors = O'Callaghan CH, Morris A, Kirby SM, Shingler AH | title = Novel method for detection of beta-lactamases by using a chromogenic cephalosporin substrate | journal = Antimicrobial Agents and Chemotherapy | volume = 1 | issue = 4 | pages = 283–8 | date = April 1972 | pmid = 4208895 | pmc = 444209 | doi = 10.1128/AAC.1.4.283 }}</ref><ref name="pmid9316913">{{cite journal | vauthors = Coudron PE, Moland ES, Sanders CC | title = Occurrence and detection of extended-spectrum beta-lactamases in members of the family Enterobacteriaceae at a veterans medical center: seek and you may find | journal = Journal of Clinical Microbiology | volume = 35 | issue = 10 | pages = 2593–7 | date = October 1997 | pmid = 9316913 | pmc = 230016 | doi = 10.1128/jcm.35.10.2593-2597.1997 }}</ref> |
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== Structure == |
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As a ], nitrocefin contains a ] ring which is susceptible to ] mediated ]. Once hydrolyzed, the degraded nitrocefin compound rapidly changes color from yellow to red. Although nitrocefin is considered a ], it does not appear to have antimicrobial properties.<ref name="O'Callaghan_1972" /> |
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== Degradation and chromogenic properties == |
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It is a semi-synthetic analogue of the naturally occurring benzyl-penicillin. |
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Intact ] antibiotics act by binding to ] (PBPs) involved in ] synthesis. ] hydrolyze the ] bond between the ] ] and the ] in the ] ring of susceptible beta-lactams and members of ] subclasses (including certain cephalosporins). After hydrolysis of the amide bond, the antibiotic lacks the ability to bind bacterial PBPs and is rendered useless. Visual detection of this process is essentially impossible with most ]s because the shift of ] absorption from the intact versus hydrolyzed product occurs outside of the ]. Hydrolysis of nitrocefin however, produces a shift of ] absorption inside the visible light spectrum from intact (yellow) nitrocefin (~380 nm) to degraded (red) nitrocefin (~500 nm) allowing visual detection of ] activity on a macroscopic level.<ref name="O'Callaghan_1972" /> |
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== Detection assays == |
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In ], carbenicillin may be preferred as a selecting agent (see ]) because its breakdown results in byproducts with a lower toxicity than analogous antibiotics like ]. Carbenicillin is more stable than ampicillin and results in less satellite colonies on selection plates.<!-- citation: <ref>{{cite web|last=Promega|title=Can carbenicillin be substituted for ampicillin when selecting for the pGEM® Vectors?|url=http://www.promega.com/resources/articles/pubhub/enotes/can-carbenicillin-be-substituted-for-ampicillin-when-selecting-for-the-pgem-vectors/|accessdate=23 August 2011}}</ref> --> However, in most situations this is not a significant problem so ] is sometimes used due to its lower cost. |
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The following assays describe methods in which nitrocefin can be used to detect ] enzymes using inexpensive materials and equipment.<ref name="Parr_1984">{{cite journal | vauthors = Parr TR, Pai CH, Bryan LE | title = Simple screening method for beta-lactamase-positive and -negative ampicillin-resistant Haemophilus influenzae isolates | journal = Journal of Clinical Microbiology | volume = 20 | issue = 1 | pages = 131–2 | date = July 1984 | pmid = 6378964 | pmc = 271264 | doi = 10.1128/jcm.20.1.131-132.1984 }}</ref> Working solutions of nitrocefin lie within 0.5 mg/mL to 1.0 mg/mL. |
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Slide Surface Assay |
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# Add one drop of 0.5 mg/ml Nitrocefin to the surface of a clean glass slide. |
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# Select a ] from an agar surface using a sterile loop and mix with the drop. |
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# Appearance of red color within 20-30 min. indicates ] activity. |
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Direct Contact Assay |
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# Place one drop of 0.5 mg/ml Nitrocefin directly on the surface of an isolated ]. |
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# Appearance of red color within 20-30 min. indicates ] activity. |
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Broth Suspension Assay |
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# Add 3-5 drops of 0.5 mg/ml Nitrocefin to 1 ml of broth suspension. |
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# Appearance of red color within 20-30 min. indicates ] activity. |
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Lysed Cell Assay |
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==Additional reading== |
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# Lyse 1ml of cell suspension by sonication. |
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* {{cite journal |author=Basker MJ, Comber KR, Sutherland R, Valler GH |title=Carfecillin: antibacterial activity in vitro and in vivo |journal=Chemotherapy |volume=23 |issue=6 |pages=424–35 |year=1977 |pmid=21771 |doi= 10.1159/000222012|url=}} |
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# Add 3-5 drops of 0.5 mg/ml Nitrocefin to lysed cell suspension. |
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# Appearance of red color within 20-30 min. indicates ] activity. |
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Filter Paper Assay |
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* {{cite journal |author=Pawełczyk E, Zajac M, Knitter B, Mikołajczak P |title=Kinetics of drug decomposition. Part 66. Kinetics of the hydrolysis of carphecillin in aqueous solution |journal=Polish journal of pharmacology and pharmacy |volume=33 |issue=3 |pages=373–86 |year=1981 |month=October |pmid=7322950 |doi= |url=}} |
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# Place a small piece of filter paper (~3 x 3 cm) in a clean petri dish or another clean isolated surface and saturate (3-5 ml) with 0.5 mg/ml Nitrocefin |
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# Select an isolated ] and smear over the surface of the impregnated filter paper. |
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# Appearance of red color within 20-30 min. indicates ] activity |
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<ref>{{cite web | title = Nitrocefin Protocol | url = http://www.toku-e.com/Assets/Protocols/Nitrocefin_Protocol.pdf | archive-url = https://web.archive.org/web/20160417193102/http://www.toku-e.com/Assets/Protocols/Nitrocefin_Protocol.pdf | archive-date = 17 April 2016 | work = TOKU-E.com }}</ref> |
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==See also== |
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{{antibiotic-stub}} |
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* ] |
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{{PenicillinAntiBiotics}} |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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