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CHEMISTRY
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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 61622-34-2, Cefotiamum, Cefotiamum [inn-latin], Ceradon, Aspil, Ctm

Molecular Formula

C₁₈H₂₃N₉O₄S₃

Molecular Weight

525.6 g/mol

InChI Key

QYQDKDWGWDOFFU-IUODEOHRSA-N

FDA UNII

91W6Z2N718

One of the CEPHALOSPORINS that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms.

1 2D Structure

Cefotiam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1

2.1.3 InChI Key

QYQDKDWGWDOFFU-IUODEOHRSA-N

2.1.4 Canonical SMILES

CN(C)CCN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)CC4=CSC(=N4)N)SC2)C(=O)O

2.1.5 Isomeric SMILES

CN(C)CCN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CC4=CSC(=N4)N)SC2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

91W6Z2N718

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Abbott 48999

2. Abbott-48999

3. Abbott48999

4. Cefotiam Hydrochloride

5. Ceradolan

6. Cgp 14221 E

7. Cgp-14221-e

8. Cgp14221e

9. Haloapor

10. Halospor

11. Hydrochloride, Cefotiam

12. Sce 963

13. Sce-963

14. Sce963

2.3.2 Depositor-Supplied Synonyms

1. 61622-34-2

2. Cefotiamum

3. Cefotiamum [inn-latin]

4. Ceradon

5. Aspil

6. Ctm

7. Cefotiam (inn)

8. J01dc07

9. Chebi:355510

10. 91w6z2n718

11. Cefotiam [inn]

12. Cefotiam [inn:ban]

13. (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

14. (6r,7r)-7-[2-(2-amino-thiazol-4-yl)-acetylamino]-3-[1-(2-dimethylamino-ethyl)-1h-tetrazol-5-ylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. Cgp 14221e

16. 66309-69-1

17. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl]thio]methyl]-8-oxo-, (6r,7r)-

18. Aspil (tn)

19. Sr-01000841230

20. Unii-91w6z2n718

21. Cefotiam,(s)

22. (6r,7r)-7-(2-(2-aminothiazol-4-yl)acetamido)-3-((1-(2-(dimethylamino)ethyl)-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

23. Cefotiam [jan]

24. Cefotiam [mi]

25. Prestwick0_000482

26. Prestwick1_000482

27. Prestwick2_000482

28. Prestwick3_000482

29. Cefotiam [who-dd]

30. Chembl1296

31. Bspbio_000343

32. Schembl149538

33. Spbio_002264

34. Bpbio1_000379

35. Dtxsid6022763

36. Schembl11224134

37. Hy-b0734

38. Zinc3830445

39. Bdbm50485561

40. Db00229

41. Ncgc00179594-01

42. (6r,7r)-7-{[(2-amino-1,3-thiazol-4-yl)acetyl]amino}-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

43. (6r,7r)-7-{[(2-amino-1,3-thiazol-4-yl)acetyl]amino}-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

44. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)acetyl)amino)-3-(((1-(2-(dimethylamino)ethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-trans)-

45. 7beta-(2-amino-1,3-thiazol-4-yl)acetamido-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-3,4-didehydrocepham-4-carboxylic Acid

46. Ab00514684

47. Cs-0009630

48. C21544

49. D07648

50. 622c342

51. J-700162

52. Q3009984

53. Sr-01000841230-2

54. Brd-k02275692-003-03-4

55. (6r,7r)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1h-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

56. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl]thio]methyl]-8-oxo-,(6r,7r)-

57. 7beta-(2-imino-4-thiazolin-4-yl)acetamido-3-{1-[2-(n,n-dimethylamino)ethyl]-1h-tetrazol-5-yl}thiomethyl-3-cephem-4-carboxylic Acid

58. 7beta-[ 2-(2-aminothiazol-4-yl) Acetamido]-3-[1-(2-dimethylaminoethyl)-1h-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₃N₉O₄S₃
Molecular Weight	525.6 g/mol
XLogP3	-2.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	10
Exact Mass	525.10351377 g/mol
Monoisotopic Mass	525.10351377 g/mol
Topological Polar Surface Area	251 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	848
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For treatment of severe infections caused by susceptible bacteria.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cefotiam is a third generation beta-lactam cephalosporin antibiotic that works by inhibiting bacterial cell wall biosynthesis. It is a broad spectrum antibiotic that is effective against Gram positive and Gram negative bacteria.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DC - Second-generation cephalosporins

J01DC07 - Cefotiam

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.