Cefotiam Hexetil

Synopsis, Chemistry

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Also known as: 95761-91-4, Cefotiam hexetil ester, Cefotiam hexetil hydrochloride, Pansporin t, Chebi:59211, J92a81y99t

Molecular Formula

C₂₇H₃₇N₉O₇S₃

Molecular Weight

695.8 g/mol

InChI Key

VVFDMWZLBPUKTD-ZKRNHDOASA-N

FDA UNII

J92A81Y99T

Cefotiam Hexetil Hydrochloride is the hydrochloride salt of cefotiam hexetil, an ester prodrug of cefotiam for parenteral use. Cefotiam is a semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. After administration of cefotiam hexetil hydrochloride the ester bond is cleaved, releasing active cefotiam.

1 2D Structure

Cefotiam Hexetil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-cyclohexyloxycarbonyloxyethyl (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-carboxylate

2.1.2 InChI

InChI=1S/C27H37N9O7S3/c1-15(42-27(40)43-18-7-5-4-6-8-18)41-24(39)21-16(13-46-26-31-32-33-35(26)10-9-34(2)3)12-44-23-20(22(38)36(21)23)30-19(37)11-17-14-45-25(28)29-17/h14-15,18,20,23H,4-13H2,1-3H3,(H2,28,29)(H,30,37)/t15?,20-,23-/m1/s1

2.1.3 InChI Key

VVFDMWZLBPUKTD-ZKRNHDOASA-N

2.1.4 Canonical SMILES

CC(OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)CC3=CSC(=N3)N)CSC4=NN=NN4CCN(C)C)OC(=O)OC5CCCCC5

2.1.5 Isomeric SMILES

CC(OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CSC(=N3)N)CSC4=NN=NN4CCN(C)C)OC(=O)OC5CCCCC5

2.2 Other Identifiers

2.2.1 UNII

J92A81Y99T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefotiam Hexetil Hydrochloride

2. Cefotiam Hexetil, (6r-(3(r*),6alpha,7beta))-isomer

3. Cefotiam Hexetil, (6r-(3(s*),6alpha,7beta))-isomer

4. Cefotiam Hexetil, (6r-(6alpha,7beta))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 95761-91-4

2. Cefotiam Hexetil Ester

3. Cefotiam Hexetil Hydrochloride

4. Pansporin T

5. Chebi:59211

6. J92a81y99t

7. Sce 2174

8. 95789-30-3

9. Cefotiam 1-(cyclohexyloxycarbonyloxy)ethyl Ester

10. 1-cyclohexyloxycarbonyloxyethyl (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-carboxylate

11. 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl (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-carboxylate

12. 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 7beta-(2-amino-1,3-thiazol-4-yl)acetamido-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-3,4-didehydrocepham-4-carboxylate

13. 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-, 1-[[(cyclohexyloxy)carbonyl]oxy]ethyl Ester, (6r,7r)-

14. Sce-2174

15. Unii-j92a81y99t

16. Cefotiam Cilexetil

17. Cefotiamhexetilester

18. 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-, 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester, (6r,7r)-

19. Schembl193201

20. Chembl3137675

21. Dtxsid20914817

22. Ncgc00483046-01

23. A900158

24. Q27126537

25. 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-, 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester, (6r-(6alpha,7beta))-

26. 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-,1-[[(cyclohexyloxy)carbonyl]oxy]ethyl Ester,dihydrochloride,(6r,7r)-

27. N-{2-[(1-{[(cyclohexyloxy)carbonyl]oxy}ethoxy)carbonyl]-3-[({1-[2-(dimethylamino)ethyl]-1h-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)ethanimidic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₇N₉O₇S₃
Molecular Weight	695.8 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	16
Exact Mass	695.19780807 g/mol
Monoisotopic Mass	695.19780807 g/mol
Topological Polar Surface Area	276 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1160
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1