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Chemistry

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Also known as: 66148-78-5, Temocillinum, Temocillina, Temocilline, Negaban, Brl 17421

Molecular Formula

C₁₆H₁₈N₂O₇S₂

Molecular Weight

414.5 g/mol

InChI Key

BVCKFLJARNKCSS-DWPRYXJFSA-N

FDA UNII

03QB156W6I

Temocillin is a semisynthetic, narrow-spectrum, beta-lactamase-resistant penicillin with antibacterial activity. Temocillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.

1 2D Structure

Temocillin Disodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1

2.1.3 InChI Key

BVCKFLJARNKCSS-DWPRYXJFSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@](C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

03QB156W6I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Brl 17421

2. Disodium 6beta-(2-carboxy-2-thien-3-ylacetamido)-6alpha-methoxypenicillanate

3. Temocillin, (2s-(2alpha,5alpha,6alpha))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 66148-78-5

2. Temocillinum

3. Temocillina

4. Temocilline

5. Negaban

6. Brl 17421

7. Brl-17421

8. N-((2s,5r,6s)-2-carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-3-thiophenemalonamic Acid

9. Brl 17421 [as Sodium]

10. (2s,5r,6s)-6-[(3-hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

11. Brl 17421 Free Acid

12. Brl-17421 Free Acid

13. Chebi:51817

14. 03qb156w6i

15. Temocillin (usan)

16. (2s,5r,6s)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

17. Temocillin [usan]

18. Temocilline [inn-french]

19. Temocillinum [inn-latin]

20. Temocillina [inn-spanish]

21. 6beta-[carboxy(thiophen-3-yl)acetamido]-6-methoxy-2,2-dimethylpenam-3alpha-carboxylic Acid

22. (2s,5r,6s)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

23. (2s,5r,6s)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

24. Einecs 266-184-1

25. Temocillin [usan:inn:ban]

26. Unii-03qb156w6i

27. Temocillin [mi]

28. Temocillin [inn]

29. Temocillin [mart.]

30. Temocillin [who-dd]

31. Schembl34084

32. Chembl1276310

33. Gtpl10926

34. Dtxsid201009398

35. Brl17421

36. Db12343

37. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6alpha))-

38. Hy-145158

39. Cs-0356857

40. D06064

41. 148t785

42. A900942

43. Q3983108

44. (2s,5r,6s)-6-(2-carboxy-2-(thiophen-3-yl)acetamido)-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

45. (2s,5r,6s)-6-[2-carboxy(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

46. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.alpha.))-

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈N₂O₇S₂
Molecular Weight	414.5 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	414.05554326 g/mol
Monoisotopic Mass	414.05554326 g/mol
Topological Polar Surface Area	187 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	700
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

4.2 ATC Code

J01CA17

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA17 - Temocillin

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