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Lactams

Organic heterocyclic compounds that contain a cyclic amide; amide groups consist of a carbonyl carbon atom linked by a single bond to a nitrogen atom and either a hydrogen or a carbon atom. These compounds are the nitrogen analogs of lactones.
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1

7-Aminodesacetoxycephalosporanic Acid, British Pharmacopoeia (BP) Reference Standard, MilliporeSigma™ Supelco™

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets, has been developed and issued under the Authority of the issuing Pharmacopoeia.

2

7-Aminocephalosporanic acid, 95-102%

CAS: 957-68-6 Molecular Formula: C10H12N2O5S Molecular Weight (g/mol): 272.27 MDL Number: MFCD00005177 InChI Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N Synonym: 7-aminocephalosporanic acid,7-aca,7-aminocephalosporinic acid,7beta-aminocephalosporanic acid,7-acs,unii-9xi67897rg,7r-7-aminocephalosporanic acid,7r-7-aminocephalosporanate,cephalosporanic acid, 7-amino,6r,7r-3-acetoxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid PubChem CID: 441328 ChEBI: CHEBI:2255 IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid SMILES: CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O

PubChem CID 441328
CAS 957-68-6
Molecular Weight (g/mol) 272.27
ChEBI CHEBI:2255
MDL Number MFCD00005177
SMILES CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O
Synonym 7-aminocephalosporanic acid,7-aca,7-aminocephalosporinic acid,7beta-aminocephalosporanic acid,7-acs,unii-9xi67897rg,7r-7-aminocephalosporanic acid,7r-7-aminocephalosporanate,cephalosporanic acid, 7-amino,6r,7r-3-acetoxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid
IUPAC Name (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI Key HSHGZXNAXBPPDL-HZGVNTEJSA-N
Molecular Formula C10H12N2O5S
3

7-Aminocephalosporanic Acid 97.0+%, TCI America™

CAS: 957-68-6 Molecular Formula: C10H12N2O5S Molecular Weight (g/mol): 272.275 MDL Number: MFCD00005177 InChI Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N Synonym: 7-aminocephalosporanic acid,7-aca,7-aminocephalosporinic acid,7beta-aminocephalosporanic acid,7-acs,unii-9xi67897rg,7r-7-aminocephalosporanic acid,7r-7-aminocephalosporanate,cephalosporanic acid, 7-amino,6r,7r-3-acetoxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid PubChem CID: 441328 ChEBI: CHEBI:2255 IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid SMILES: CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O

PubChem CID 441328
CAS 957-68-6
Molecular Weight (g/mol) 272.275
ChEBI CHEBI:2255
MDL Number MFCD00005177
SMILES CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O
Synonym 7-aminocephalosporanic acid,7-aca,7-aminocephalosporinic acid,7beta-aminocephalosporanic acid,7-acs,unii-9xi67897rg,7r-7-aminocephalosporanic acid,7r-7-aminocephalosporanate,cephalosporanic acid, 7-amino,6r,7r-3-acetoxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid
IUPAC Name (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI Key HSHGZXNAXBPPDL-HZGVNTEJSA-N
Molecular Formula C10H12N2O5S
4

7-Aminodesacetoxycephalosporanic Acid 98.0+%, TCI America™

CAS: 22252-43-3 Molecular Formula: C8H10N2O3S Molecular Weight (g/mol): 214.239 MDL Number: MFCD00151456 InChI Key: NVIAYEIXYQCDAN-CLZZGJSISA-N Synonym: 7-aminodesacetoxycephalosporanic acid,6r,7r-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid,7-aminodeacetoxycephalosporanic acid,7-adca,unii-anm3msm8tn,anm3msm8tn,7beta-amino-3-methyl-3-cephem-4-carboxylic acid,7beta-amino-3-methylceph-3-em-4-carboxylic acid,7-amino desacetoxy cephalosporanic acid,7beta-aminodeacetoxycephalosporanic acid PubChem CID: 33498 ChEBI: CHEBI:64984 IUPAC Name: (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid SMILES: CC1=C(N2C(C(C2=O)N)SC1)C(=O)O

PubChem CID 33498
CAS 22252-43-3
Molecular Weight (g/mol) 214.239
ChEBI CHEBI:64984
MDL Number MFCD00151456
SMILES CC1=C(N2C(C(C2=O)N)SC1)C(=O)O
Synonym 7-aminodesacetoxycephalosporanic acid,6r,7r-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid,7-aminodeacetoxycephalosporanic acid,7-adca,unii-anm3msm8tn,anm3msm8tn,7beta-amino-3-methyl-3-cephem-4-carboxylic acid,7beta-amino-3-methylceph-3-em-4-carboxylic acid,7-amino desacetoxy cephalosporanic acid,7beta-aminodeacetoxycephalosporanic acid
IUPAC Name (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI Key NVIAYEIXYQCDAN-CLZZGJSISA-N
Molecular Formula C8H10N2O3S
5

Sulbactam 98.0+%, TCI America™

CAS: 68373-14-8 Molecular Formula: C8H11NO5S Molecular Weight (g/mol): 233.24 MDL Number: MFCD00867005 InChI Key: FKENQMMABCRJMK-RITPCOANSA-N Synonym: sulbactam,sulbactam acid,penicillanic acid sulfone,sulbactamum,betamaze,2s,5r-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide,penicillanic acid 1,1-dioxide,unii-s4tf6i2330,penicillanic acid dioxide,chembl403 PubChem CID: 130313 ChEBI: CHEBI:9321 IUPAC Name: (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid SMILES: CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O

PubChem CID 130313
CAS 68373-14-8
Molecular Weight (g/mol) 233.24
ChEBI CHEBI:9321
MDL Number MFCD00867005
SMILES CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O
Synonym sulbactam,sulbactam acid,penicillanic acid sulfone,sulbactamum,betamaze,2s,5r-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide,penicillanic acid 1,1-dioxide,unii-s4tf6i2330,penicillanic acid dioxide,chembl403
IUPAC Name (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI Key FKENQMMABCRJMK-RITPCOANSA-N
Molecular Formula C8H11NO5S
6

Sulbactam, 98%

CAS: 68373-14-8 Molecular Formula: C8H11NO5S Molecular Weight (g/mol): 233.24 MDL Number: MFCD00867005 InChI Key: FKENQMMABCRJMK-RITPCOANSA-N Synonym: sulbactam,sulbactam acid,penicillanic acid sulfone,sulbactamum,betamaze,2s,5r-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide,penicillanic acid 1,1-dioxide,unii-s4tf6i2330,penicillanic acid dioxide,chembl403 PubChem CID: 130313 ChEBI: CHEBI:9321 IUPAC Name: (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid SMILES: CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O

PubChem CID 130313
CAS 68373-14-8
Molecular Weight (g/mol) 233.24
ChEBI CHEBI:9321
MDL Number MFCD00867005
SMILES CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O
Synonym sulbactam,sulbactam acid,penicillanic acid sulfone,sulbactamum,betamaze,2s,5r-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide,penicillanic acid 1,1-dioxide,unii-s4tf6i2330,penicillanic acid dioxide,chembl403
IUPAC Name (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI Key FKENQMMABCRJMK-RITPCOANSA-N
Molecular Formula C8H11NO5S
7

Aztreonam 98.0+%, TCI America™

CAS: 78110-38-0 Molecular Formula: C13H17N5O8S2 Molecular Weight (g/mol): 435.426 MDL Number: MFCD00072145 InChI Key: WZPBZJONDBGPKJ-PSGLRMFWSA-N Synonym: trans-2-1-2-aminothiazol-4-yl-2-2-methyl-4-oxo-1-sulphoazetidin-3-yl amino-2-oxoethylidene amino oxy-2-methylpropionic acid,2-1-2-amino-4-thiazolyl-2-2r-2alpha-methyl-4-oxo-1-sulfo-3beta-azetidinyl amino-2-oxoethylidene amino oxy-2-methylpropanoic acid PubChem CID: 56842327 IUPAC Name: 2-[(E)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2R,3R)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid SMILES: CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N

PubChem CID 56842327
CAS 78110-38-0
Molecular Weight (g/mol) 435.426
MDL Number MFCD00072145
SMILES CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N
Synonym trans-2-1-2-aminothiazol-4-yl-2-2-methyl-4-oxo-1-sulphoazetidin-3-yl amino-2-oxoethylidene amino oxy-2-methylpropionic acid,2-1-2-amino-4-thiazolyl-2-2r-2alpha-methyl-4-oxo-1-sulfo-3beta-azetidinyl amino-2-oxoethylidene amino oxy-2-methylpropanoic acid
IUPAC Name 2-[(E)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2R,3R)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
InChI Key WZPBZJONDBGPKJ-PSGLRMFWSA-N
Molecular Formula C13H17N5O8S2
8

Tazobactam, 94%

CAS: 89786-04-9 Molecular Formula: C10H12N4O5S Molecular Weight (g/mol): 300.29 MDL Number: MFCD00917472 MFCD00867002 InChI Key: LPQZKKCYTLCDGQ-WEDXCCLWSA-N Synonym: tazobactam,tazobactam acid,tazobactamum,zosyn,unii-se10g96m8w,ytr-830h,ytr 830h,chembl404,ytr830h,2s,3s,5r-3-methyl-7-oxo-3-1h-1,2,3-triazol-1-ylmethyl-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide PubChem CID: 123630 ChEBI: CHEBI:9421 IUPAC Name: (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid SMILES: C[C@]1(CN2C=CN=N2)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O

PubChem CID 123630
CAS 89786-04-9
Molecular Weight (g/mol) 300.29
ChEBI CHEBI:9421
MDL Number MFCD00917472 MFCD00867002
SMILES C[C@]1(CN2C=CN=N2)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O
Synonym tazobactam,tazobactam acid,tazobactamum,zosyn,unii-se10g96m8w,ytr-830h,ytr 830h,chembl404,ytr830h,2s,3s,5r-3-methyl-7-oxo-3-1h-1,2,3-triazol-1-ylmethyl-4-thia-1-azabicyclo 3.2.0 heptane-2-carboxylic acid 4,4-dioxide
IUPAC Name (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI Key LPQZKKCYTLCDGQ-WEDXCCLWSA-N
Molecular Formula C10H12N4O5S
9

Tazobactam sodium

CAS: 89785-84-2 Molecular Formula: C10H12N4NaO5S Molecular Weight (g/mol): 323.279 MDL Number: MFCD00917472 InChI Key: ZUNWFYFXHGWFRA-QVUDESDKSA-N Synonym: tazobactam sodium salt PubChem CID: 66636300 IUPAC Name: (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;sodium SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na]

PubChem CID 66636300
CAS 89785-84-2
Molecular Weight (g/mol) 323.279
MDL Number MFCD00917472
SMILES CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na]
Synonym tazobactam sodium salt
IUPAC Name (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;sodium
InChI Key ZUNWFYFXHGWFRA-QVUDESDKSA-N
Molecular Formula C10H12N4NaO5S
10

Strychnine Sulfate Pentahydrate 97.0+%, TCI America™

CAS: 60491-10-3 Molecular Formula: C42H56N4O13S Molecular Weight (g/mol): 856.985 MDL Number: MFCD00068328 InChI Key: FDQUTDUZMOOVST-ZKOSLKCXSA-N PubChem CID: 76965789 IUPAC Name: (4aR,5aS,8aR,13aS,15aS,15bR)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid;pentahydrate SMILES: C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75.C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75.O.O.O.O.O.OS(=O)(=O)O

PubChem CID 76965789
CAS 60491-10-3
Molecular Weight (g/mol) 856.985
MDL Number MFCD00068328
SMILES C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75.C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75.O.O.O.O.O.OS(=O)(=O)O
IUPAC Name (4aR,5aS,8aR,13aS,15aS,15bR)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid;pentahydrate
InChI Key FDQUTDUZMOOVST-ZKOSLKCXSA-N
Molecular Formula C42H56N4O13S
11

Brucine sulfate hydrate, 98% (dry wt.), water <13%

CAS: 652154-10-4 Molecular Formula: C46H54N4O12S Molecular Weight (g/mol): 887.01 MDL Number: MFCD00013472 InChI Key: HCMSIGALSOEZRW-MDQLRNFDSA-N Synonym: brucine sulfate salt PubChem CID: 118797651 IUPAC Name: 10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid;hydrate SMILES: OS(O)(=O)=O.[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C([C@@]35[H])[C@]1(CCN2C4)C1=C6C=C(OC)C(OC)=C1.[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C([C@@]35[H])[C@]1(CCN2C4)C1=C6C=C(OC)C(OC)=C1

PubChem CID 118797651
CAS 652154-10-4
Molecular Weight (g/mol) 887.01
MDL Number MFCD00013472
SMILES OS(O)(=O)=O.[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C([C@@]35[H])[C@]1(CCN2C4)C1=C6C=C(OC)C(OC)=C1.[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C([C@@]35[H])[C@]1(CCN2C4)C1=C6C=C(OC)C(OC)=C1
Synonym brucine sulfate salt
IUPAC Name 10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid;hydrate
InChI Key HCMSIGALSOEZRW-MDQLRNFDSA-N
Molecular Formula C46H54N4O12S