Nafcillin Sodium

Synopsis, Chemistry

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Also known as: 985-16-0, Sodium nafcillin, Nafcillin sodium salt, Nafcillin sodium anhydrous, Nafcillin sodium, Nafcillin (sodium)

Molecular Formula

C₂₁H₂₁N₂NaO₅S

Molecular Weight

436.5 g/mol

InChI Key

AYAPZOUDXCDGIF-FRFVDRIFSA-M

FDA UNII

SY07234TTS

A semi-synthetic antibiotic related to penicillin.

1 2D Structure

Nafcillin Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C21H22N2O5S.Na/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);/q;+1/p-1/t15-,16+,19-;/m1./s1

2.1.3 InChI Key

AYAPZOUDXCDGIF-FRFVDRIFSA-M

2.1.4 Canonical SMILES

CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]

2.1.5 Isomeric SMILES

CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

SY07234TTS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Nafcil

2. Nafcillin

3. Nafcillin, Monosodium Salt, Anhydrous

4. Nafcillin, Sodium

5. Naphthamidopenicillin

6. Sodium Nafcillin

7. Sodium, Nafcillin

2.3.2 Depositor-Supplied Synonyms

1. 985-16-0

2. Sodium Nafcillin

3. Nafcillin Sodium Salt

4. Nafcillin Sodium Anhydrous

5. Nafcillin Sodium

6. Nafcillin (sodium)

7. 6-(2-ethoxy-1-naphthamido)penicillin Sodium

8. Sodium 6-(2-ethoxy-1-naphthamido)penicillanate

9. Mls000069582

10. Chebi:7448

11. Sy07234tts

12. 6-[2-ethoxy-1-naphthamido]-penicillin Sodium Salt

13. Naftopen

14. Smr000058840

15. Sodium;(2s,5r,6r)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

16. Anhydrous Nafcillin Sodium

17. Brl 1383

18. Einecs 213-574-4

19. Unii-sy07234tts

20. Nallpen In Plastic Container

21. Unipen In Plastic Container

22. Sodium (2s,5r,6r)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

23. Opera_id_510

24. Schembl34125

25. Chembl1200344

26. Hy-b0555b

27. Dtxsid00904716

28. Nafcillin Sodium [who-dd]

29. Hms2236l03

30. Hms3259o22

31. Str11060

32. Mfcd00056863

33. Nc00606

34. Ncgc00386250-01

35. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amido)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s,5r,6r)-

36. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-, Monosodium Salt

37. Sodium (2s-(2alpha,5alpha,6beta))-6-(((2-ethoxy-1-naphthyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

38. Anhydrous Nafcillin Sodium [mart.]

39. Cs-0129337

40. Nafcillin Sodium Salt Anhydrous [mi]

41. C08124

42. Ab01566906_01

43. 6-(2-ethoxy-1-naphthamido)penicillin Sodium Salt

44. W-100077

45. Q27107495

46. Sodium 6beta-(2-ethoxynaphthalene-1-carboxamido)-2,2-dimethylpenam-3alpha-carboxylate

47. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s,5r,6r)-

48. Sodium (2s,5r,6r)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

49. Sodium (2s,5r,6r)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₁N₂NaO₅S
Molecular Weight	436.5 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	436.10688723 g/mol
Monoisotopic Mass	436.10688723 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	705
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Nafcillin sodium
Drug Label	Nafcillin for Injection, USP is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. It is the sodium salt in a parenteral dosage form. The chemical name of nafcillin sodium is monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-...
Active Ingredient	Nafcillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Istituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

2 of 4
Drug Name	Nallpen in plastic container
Active Ingredient	Nafcillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/100ml; eq 20mg base/ml
Market Status	Prescription
Company	Baxter Hlthcare

3 of 4
Drug Name	Nafcillin sodium
Drug Label	Nafcillin for Injection, USP is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. It is the sodium salt in a parenteral dosage form. The chemical name of nafcillin sodium is monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-...
Active Ingredient	Nafcillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Istituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

4 of 4
Drug Name	Nallpen in plastic container
Active Ingredient	Nafcillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/100ml; eq 20mg base/ml
Market Status	Prescription
Company	Baxter Hlthcare