Sultamicillin

Synopsis, Chemistry

PRICE INFORMATION

API Reference Price, API Exports, API Imports, FDF Imports

DOSSIERs // Finished Dosage Formulations

7 Dossiers, 2 Europe, 5 Listed Dossiers

GLOBAL SALES INFORMATION

2 Finished Drug Prices

2 Finished Drug Prices

MARKET PLACE

5 APIs

5 APIs

REF. STANDARDS & IMPURITIES

1 Others

1 Others

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

EU WC

Listed Suppliers

API REF. PRICE (USD / KG)

205

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: 76497-13-7, Sultamicilina, Sultamicillinum, Sultamicillin tosylate, Vd 1827, Cp-49,952

Molecular Formula

C₂₅H₃₀N₄O₉S₂

Molecular Weight

594.7 g/mol

InChI Key

OPYGFNJSCUDTBT-PMLPCWDUSA-N

FDA UNII

65DT0ML581

Sultamicillin is a combination formulation of the sodium salts of the antibiotic ampicillin and the beta-lactamase inhibitor sulbactam with antibacterial activity. Ampicillin, a broad-spectrum, semisynthetic penicillin, binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall, thereby interfering with the cross-linking of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. As a result, the cell wall is weakened and the cell lyses. The sulbactam component irreversibly binds to bacterial beta-lactamase at or near its active site, thereby interfering with substrate binding and inhibiting bacterial metabolism of penicillin and cephalosporin beta-lactam antibiotics, effectively extending their antibiotic spectrum to include many beta-lactam-resistant bacteria.

1 2D Structure

Sultamicillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-46-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1

2.1.3 InChI Key

OPYGFNJSCUDTBT-PMLPCWDUSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OCOC(=O)C4C(S(=O)(=O)C5N4C(=O)C5)(C)C)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)[C@H]4C(S(=O)(=O)[C@H]5N4C(=O)C5)(C)C)C

2.2 Other Identifiers

2.2.1 UNII

65DT0ML581

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ampicillin-sulbactam

2. Combisid

3. Cp 49,952

4. Cp 49952

5. Unasyn

2.3.2 Depositor-Supplied Synonyms

1. 76497-13-7

2. Sultamicilina

3. Sultamicillinum

4. Sultamicillin Tosylate

5. Vd 1827

6. Cp-49,952

7. Chebi:51770

8. 65dt0ml581

9. 76497-13-7 (free)

10. Unacid

11. Vd-1827

12. Cp-49952

13. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,[[[(2s,5r)-3,3-dimethyl-4,4-dioxido-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]oxy]methylester, (2s,5r,6r)-

14. Hydroxymethyl (2s,5r,6r)-6-((r)-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate, (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate (ester) S,s-dioxide

15. (((2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl)oxy)methyl (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

16. ({6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carbonyl}oxy)methyl 2,2-dimethylpenam-3alpha-carboxylate 1,1-dioxide

17. [(2,2-dimethyl-1,1-dioxidopenam-3alpha-carbonyl)oxy]methyl 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate

18. Sultamicilina [spanish]

19. Sultamicillinum [latin]

20. Cp 49952

21. Unii-65dt0ml581

22. Sultamicillin [usan:inn:ban]

23. Sultamicillin [mi]

24. Sultamicillin [inn]

25. Sultamicillin (usan/inn)

26. Sultamicillin [usan]

27. Schembl34392

28. Sultamicillin [mart.]

29. Sultamicillin [who-dd]

30. Chembl506110

31. Dtxsid501010077

32. Hy-n7115

33. Sultamicillin [ep Monograph]

34. Sultamicillin For Peak Identification

35. S5411

36. Zinc42834847

37. Akos015963376

38. Ccg-270182

39. Db12127

40. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonyloxymethyl (2s,5r,6r)-6-((r)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat

41. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (((3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-2-yl)carbonyl)oxy)methyl Ester, S,s-dioxide, (2s-(2alpha(2r*,5s*),5alpha,6beta(s*)))-

42. As-14087

43. Cs-0082687

44. D05972

45. 497s137

46. 6'-(2-amino-2-phenylacetamido)penicillanoyloxymethyl Penicillanate 1,1-dioxide

47. [(2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

48. 1,1-dioxopenicillanoyloxymethyl 6-(d-.alpha.-amino-.alpha.-phenylacetamido)penicillanate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₀N₄O₉S₂
Molecular Weight	594.7 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	594.14542089 g/mol
Monoisotopic Mass	594.14542089 g/mol
Topological Polar Surface Area	216 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1240
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1