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

Popular Products

Tebipenem
CAS: 161715-21-5 PubChem CID: 9800194 Formula: C₁₆H₂₁N₃O₄S₂ Molecular Weight: 383.5

≥98%

Out of Stock Item #: T648048

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Technical Identifiers

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

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/s1

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...
Meropenem-d6
CAS: 1217976-95-8 Formula: C₁₇H₁₉D₆N₃O₅S Molecular Weight: 389.5

Out of Stock Item #: M646345

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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

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-,12-/mshow more
tomopenem
CAS: 222400-20-6 PubChem CID: 9809656

Moligand™ ?

Out of Stock Item #: T614503

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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

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/h10-14,16-17,31H,4-9show 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...
tacapenem
CAS: 193811-33-5 PubChem CID: 73302

Moligand™ ?

Out of Stock Item #: T614301

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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

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-/m1/s1

Synonyms
5216EI628Q | Q27260941 | (4R,5S,6S)-6-((R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((R)-5-oxopyrrolidin-3-yl)thio)-1-azabic...
panipenem
CAS: 87726-17-8 EC Number: 841-739-6 PubChem CID: 72015

Moligand™ ?

Out of Stock Item #: P612622

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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

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...
lenapenem
CAS: 149951-16-6 PubChem CID: 216262

Moligand™ ?

Out of Stock Item #: L611484

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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

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-,10+,11show more

Synonyms
Lenapenem [INN] | Q27276182 | BO2727 | BO-2727 | (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(m...
E-1010 free base
Moligand™ ?

Out of Stock Item #: E610038

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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

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,26,27)/t8-,show 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...
Meropenem trihydrate
CAS: 119478-56-7 PubChem CID: 441129 Formula: C₁₇H₂₅N₃O₅S·3H₂O Molecular Weight: 437.51

10mM in DMSO

In Stock Item #: M420860

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Technical Identifiers

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

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-,8-,9+show more

Synonyms
s4846 | (4R,5S,6S)-3-(((3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza...
Meropenem
CAS: 96036-03-2 EC Number: 641-424-1 Formula: C₁₇H₂₅N₃O₅S Molecular Weight: 383.47

Moligand™ ? 10mM in DMSO

In Stock Item #: M427157

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Technical Identifiers

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

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-,12-/mshow more

Synonyms
Tox21_113794 | (1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-YLTHIO]-6-[(R)-1-HYDROXYETHYL]-1-METHYLCARBA...
Imipenem monohydrate
CAS: 74431-23-5 EC Number: 264-734-5 PubChem CID: 5282372 Formula: C₁₂H₁₇N₃O₄S · H₂O Molecular Weight: 317.36

10mM in Water

In Stock Item #: I425795

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Technical Identifiers

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

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
(5R,6S)-3-((2-Formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid h...
Doripenem Hydrate
CAS: 364622-82-2 EC Number: 680-392-3 PubChem CID: 636377 Formula: C₁₅H₂₄N₄O₆S₂·H₂O Molecular Weight: 438.52

10mM in DMSO

In Stock Item #: D423634

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Technical Identifiers

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

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)(H2,16,24,25show more

Synonyms
CCG-269113 | (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)t...
Doripenem
CAS: 148016-81-3 Formula: C₁₅H₂₄N₄O₆S₂ Molecular Weight: 420.5

Moligand™ ? 10mM in DMSO

In Stock Item #: D421732

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Technical Identifiers

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

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)(H2,16,24,25)/t6-show more

Synonyms
(+)-(4R,5S,6S)-6-((1R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)-3-pyrrolidinyl)thio)-1-a...

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