Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:51:59 UTC |
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HMDB ID | HMDB0015426 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cefoxitin |
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Description | Cefoxitin is only found in individuals that have used or taken this drug. It is a semi-synthetic, broad-spectrum cepha antibiotic for intravenous administration. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans.The bactericidal action of cefoxitin results from inhibition of cell wall synthesis. |
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Structure | [H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)CC1=CC=CS1)OC)C(O)=O InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1 |
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Synonyms | Value | Source |
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(6R,7S)-3-[(Carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | ChEBI | Cefoxitina | ChEBI | Cefoxitine | ChEBI | Cefoxitinum | ChEBI | Ceftoxitin | ChEBI | Cephoxitin | ChEBI | CFX | ChEBI | Rephoxitin | ChEBI | (6R,7S)-3-[(Carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | Generator | MSD Brand OF cefoxitin sodium | HMDB | Sodium, cefoxitin | HMDB | Merck brand OF cefoxitin sodium | HMDB | Cefoxitin sodium | HMDB | Mefoxitin | HMDB | Mefoxin | HMDB | Merck frosst brand OF cefoxitin sodium | HMDB | Merck sharp and dohme brand OF cefoxitin sodium | HMDB | Méfoxin | HMDB |
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Chemical Formula | C16H17N3O7S2 |
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Average Molecular Weight | 427.452 |
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Monoisotopic Molecular Weight | 427.050791293 |
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IUPAC Name | (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
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Traditional Name | cefoxitin |
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CAS Registry Number | 35607-66-0 |
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SMILES | [H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)CC1=CC=CS1)OC)C(O)=O |
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InChI Identifier | InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1 |
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InChI Key | WZOZEZRFJCJXNZ-ZBFHGGJFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid esters |
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Direct Parent | Steroid esters |
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Alternative Parents | |
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Substituents | - Steroid ester
- Androstane-skeleton
- N-methylpiperazine
- N-alkylpiperazine
- 1,4-diazinane
- Dicarboxylic acid or derivatives
- Piperazine
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Amino acid or derivatives
- Carboxylic acid ester
- Tertiary amine
- Tertiary aliphatic amine
- Azacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Carbonyl group
- Organic nitrogen compound
- Organic salt
- Organic cation
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 149.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.2 g/L | Not Available | LogP | -0.02 | SANGSTER (1993) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Cefoxitin,1TMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3379.0 | Semi standard non polar | 33892256 | Cefoxitin,1TMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3416.2 | Semi standard non polar | 33892256 | Cefoxitin,1TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21 | 3311.4 | Semi standard non polar | 33892256 | Cefoxitin,2TMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3368.3 | Semi standard non polar | 33892256 | Cefoxitin,2TMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3098.9 | Standard non polar | 33892256 | Cefoxitin,2TMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 5340.3 | Standard polar | 33892256 | Cefoxitin,2TMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3242.6 | Semi standard non polar | 33892256 | Cefoxitin,2TMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3063.5 | Standard non polar | 33892256 | Cefoxitin,2TMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 5577.6 | Standard polar | 33892256 | Cefoxitin,2TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3310.2 | Semi standard non polar | 33892256 | Cefoxitin,2TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3173.3 | Standard non polar | 33892256 | Cefoxitin,2TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 5038.9 | Standard polar | 33892256 | Cefoxitin,2TMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3317.9 | Semi standard non polar | 33892256 | Cefoxitin,2TMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3194.1 | Standard non polar | 33892256 | Cefoxitin,2TMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 5169.3 | Standard polar | 33892256 | Cefoxitin,3TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3248.6 | Semi standard non polar | 33892256 | Cefoxitin,3TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 3189.4 | Standard non polar | 33892256 | Cefoxitin,3TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N[Si](C)(C)C)CS[C@@H]21 | 4697.1 | Standard polar | 33892256 | Cefoxitin,3TMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3289.4 | Semi standard non polar | 33892256 | Cefoxitin,3TMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3207.4 | Standard non polar | 33892256 | Cefoxitin,3TMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 4944.6 | Standard polar | 33892256 | Cefoxitin,3TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3260.7 | Semi standard non polar | 33892256 | Cefoxitin,3TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3287.0 | Standard non polar | 33892256 | Cefoxitin,3TMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 4635.9 | Standard polar | 33892256 | Cefoxitin,4TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3249.3 | Semi standard non polar | 33892256 | Cefoxitin,4TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 3298.8 | Standard non polar | 33892256 | Cefoxitin,4TMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)CS[C@@H]21 | 4332.6 | Standard polar | 33892256 | Cefoxitin,1TBDMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3574.4 | Semi standard non polar | 33892256 | Cefoxitin,1TBDMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3624.6 | Semi standard non polar | 33892256 | Cefoxitin,1TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21 | 3531.5 | Semi standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3741.6 | Semi standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3455.0 | Standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #1 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 5201.8 | Standard polar | 33892256 | Cefoxitin,2TBDMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3648.6 | Semi standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 3447.9 | Standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #2 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(N)=O)CS[C@@H]21 | 5405.0 | Standard polar | 33892256 | Cefoxitin,2TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3712.8 | Semi standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3528.5 | Standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4902.2 | Standard polar | 33892256 | Cefoxitin,2TBDMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3751.3 | Semi standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3548.6 | Standard non polar | 33892256 | Cefoxitin,2TBDMS,isomer #4 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 5031.9 | Standard polar | 33892256 | Cefoxitin,3TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3824.7 | Semi standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3714.4 | Standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4674.6 | Standard polar | 33892256 | Cefoxitin,3TBDMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3894.4 | Semi standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3722.4 | Standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #2 | CO[C@@]1(NC(=O)CC2=CC=CS2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4863.6 | Standard polar | 33892256 | Cefoxitin,3TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3893.1 | Semi standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3807.6 | Standard non polar | 33892256 | Cefoxitin,3TBDMS,isomer #3 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4612.4 | Standard polar | 33892256 | Cefoxitin,4TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4014.7 | Semi standard non polar | 33892256 | Cefoxitin,4TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 3975.5 | Standard non polar | 33892256 | Cefoxitin,4TBDMS,isomer #1 | CO[C@@]1(N(C(=O)CC2=CC=CS2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CS[C@@H]21 | 4414.1 | Standard polar | 33892256 |
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