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Thienamycins

Description:

Beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Ancestors:

Organic compounds ⮕ Organoheterocyclic compounds ⮕ Lactams ⮕ Beta lactams ⮕ Carbapenems ⮕ Thienamycins
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Items 1-12 of 20

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  1. Tebipenem
      Grade & Purity: 
    • ≥98%
    Cas Number: 161715-21-5        Compound CID:  9800194
    Formula:  C16H21N3O4S2        Molecular Weight: 383.5
    IUPAC Name:  (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicshow more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)O)C(C)O
    InChIKey: GXXLUDOKHXEFBQ-YJFSRANCSA-N
    InChI:  InChI=1S/C16H21N3O4S2/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)25-9-5-18(6-9)16-17-3-4-24-16/h7-11,20H,3-6H2,1-2H3,(H,22,23)/t7-,8-,10-,11-/m1/sshow more
    Synonyms: 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1R)-1-hydroxy...
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  2. Meropenem-d6
    Cas Number: 1217976-95-8
    Formula:  C17H19D6N3O5S        Molecular Weight: 389.5
    IUPAC Name:  (4R,5S,6S)-3-[(3S,5S)-5-[bis(trideuteriomethyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-eneshow more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
    InChIKey: DMJNNHOOLUXYBV-ZSJYILIPSA-N
    InChI:  InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-show more
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  3. tomopenem
    Cas Number: 222400-20-6        Compound CID:  9809656
    IUPAC Name:  (4R,5S,6S)-3-[(3S,5S)-5-[(3S)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyetshow more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(N(C3)C)C(=O)N4CCC(C4)NC(=O)CN=C(N)N)C(=O)O)C(C)O
    InChIKey: KEDAXBWZURNCHS-GPODMPQUSA-N
    InChI:  InChI=1S/C23H35N7O6S/c1-10-17-16(11(2)31)21(34)30(17)18(22(35)36)19(10)37-13-6-14(28(3)9-13)20(33)29-5-4-12(8-29)27-15(32)7-26-23(24)25/h10-14,16-17,3show more
    Synonyms: 1654W9611T | R 1558 | CS 023 | BDBM50385714 | (1r,5s,6s)-6-[(1r)-1-hydroxyethyl]-1-methyl-2-[(2s,4s)-2-[(3s)-3-(2-gua...
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  4. tacapenem
    Cas Number: 193811-33-5        Compound CID:  73302
    IUPAC Name:  (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3R)-5-oxopyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
    SMILES:  O=C1NC[C@@H](C1)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C
    InChIKey: CTEFNVKDRWMZSL-CTNSIQBBSA-N
    InChI:  InChI=1S/C14H18N2O5S/c1-5-10-9(6(2)17)13(19)16(10)11(14(20)21)12(5)22-7-3-8(18)15-4-7/h5-7,9-10,17H,3-4H2,1-2H3,(H,15,18)(H,20,21)/t5-,6-,7-,9-,10-/m1show more
    Synonyms: 5216EI628Q | Q27260941 | (4R,5S,6S)-6-((R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((R)-5-oxopyrrolidin-3-yl)thio)-1-azabic...
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  5. panipenem
    Cas Number: 87726-17-8        EC Number: 841-739-6        Compound CID:  72015
    IUPAC Name:  (5R,6S)-3-[(3S)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
    SMILES:  CC(C1C2CC(=C(N2C1=O)C(=O)O)SC3CCN(C3)C(=N)C)O
    InChIKey: TYMABNNERDVXID-DLYFRVTGSA-N
    InChI:  InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1
    Synonyms: HY-111227 | PANIPENEM [INN] | PAPM | (5R,6S)-3-[(3S)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-7...
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  6. lenapenem
    Cas Number: 149951-16-6        Compound CID:  216262
    IUPAC Name:  (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-show more
    SMILES:  CNCC[C@H]([C@H]1NC[C@H](C1)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C)O
    InChIKey: PZLOCBSBEUDCPF-YJIVIRPOSA-N
    InChI:  InChI=1S/C18H29N3O5S/c1-8-14-13(9(2)22)17(24)21(14)15(18(25)26)16(8)27-10-6-11(20-7-10)12(23)4-5-19-3/h8-14,19-20,22-23H,4-7H2,1-3H3,(H,25,26)/t8-,9-,show more
    Synonyms: Lenapenem [INN] | Q27276182 | BO2727 | BO-2727 | (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(m...
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  7. E-1010 free base
    IUPAC Name:  (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(R)-hydroxy-[(3R)-pyrrolidin-3-yl]methyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hshow more
    SMILES:  C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)[C@@H]([C@H]1CNCC1)O)O
    InChIKey: QYOLGBCSUXWEKY-ANTKKXPTSA-N
    InChI:  InChI=1S/C19H29N3O5S/c1-8-14-13(9(2)23)18(25)22(14)15(19(26)27)17(8)28-11-5-12(21-7-11)16(24)10-3-4-20-6-10/h8-14,16,20-21,23-24H,3-7H2,1-2H3,(H,26,27show more
    Synonyms: ER-35786 free base | 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 6-((1R)-1-hydroxyethyl)-3-(((3S,5S)-5-((R)-hydr...
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  8. Meropenem trihydrate
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 119478-56-7        Compound CID:  441129
    Formula:  C17H25N3O5S·3H2O        Molecular Weight: 437.51
    IUPAC Name:  (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic show more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O.O.O.O
    InChIKey: CTUAQTBUVLKNDJ-OBZXMJSBSA-N
    InChI:  InChI=1S/C17H25N3O5S.3H2O/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4;;;/h7-12,18,21H,5-6H2,1-4H3,(H,24,25);3*1H2/t7-show more
    Synonyms: Meropenem trihydrate|119478-56-7|Meropenem (trihydrate)|FV9J3JU8B1|UNII-FV9J3JU8B1|(4R,5S,6S)-3-{[(3S,5S)-5-(dimethyl...
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  9. Meropenem
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 96036-03-2
    Formula:  C17H25N3O5S        Molecular Weight: 383.47
    IUPAC Name:  (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic show more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
    InChIKey: DMJNNHOOLUXYBV-PQTSNVLCSA-N
    InChI:  InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-show more
    Synonyms: meropenem|96036-03-2|Merrem|Meropenem anhydrous|Meropenemum|Antibiotic SM 7338|MERONEM|Merrem I.V.|MEPM|119478-56-7|M...
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  10. Imipenem monohydrate
      Grade & Purity: 
    • 10mM in Water
    Cas Number: 74431-23-5        EC Number: 264-734-5        Compound CID:  5282372
    Formula:  C12H17N3O4S · H2O        Molecular Weight: 317.36
    IUPAC Name:  (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;hydrate
    SMILES:  CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O.O
    InChIKey: GSOSVVULSKVSLQ-JJVRHELESA-N
    InChI:  InChI=1S/C12H17N3O4S.H2O/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17;/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19);1H2/t6-,7-,9-;/m1./s1
    Synonyms: Imipenem monohydrate|74431-23-5|Imipenem hydrate|(5R,6S)-3-((2-Formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-...
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  11. Doripenem Hydrate
      Grade & Purity: 
    • 10mM in DMSO
    Cas Number: 364622-82-2        Compound CID:  636377
    Formula:  C15H24N4O6S2·H2O        Molecular Weight: 438.52
    IUPAC Name:  (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxshow more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(NC3)CNS(=O)(=O)N)C(=O)O)C(C)O.O
    InChIKey: NTUBEBXBDGKBTJ-WGLOMNHJSA-N
    InChI:  InChI=1S/C15H24N4O6S2.H2O/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25;/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16show more
    Synonyms: CCG-269113 | CS-2076 | (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrroli...
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  12. Doripenem
    Cas Number: 148016-81-3
    Formula:  C15H24N4O6S2        Molecular Weight: 420.5
    IUPAC Name:  (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxshow more
    SMILES:  CC1C2C(C(=O)N2C(=C1SC3CC(NC3)CNS(=O)(=O)N)C(=O)O)C(C)O
    InChIKey: AVAACINZEOAHHE-VFZPANTDSA-N
    InChI:  InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,2show more
    Synonyms: Doripenem|148016-81-3|Doribax|Finibax|S-4661|UNII-BHV525JOBH|BHV525JOBH|DTXSID2046678|(4R,5S,6S)-6-[(1R)-1-hydroxyeth...
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