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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

Nafcillin Sodium
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 Weight 436.5 g/mol
Molecular Formula C21H21N2NaO5S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass436.10688723 g/mol
Monoisotopic Mass436.10688723 g/mol
Topological Polar Surface Area124 Ų
Heavy Atom Count30
Formal Charge0
Complexity705
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameNafcillin sodium
Drug LabelNafcillin 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 IngredientNafcillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyIstituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

2 of 4  
Drug NameNallpen in plastic container
Active IngredientNafcillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/100ml; eq 20mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

3 of 4  
Drug NameNafcillin sodium
Drug LabelNafcillin 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 IngredientNafcillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyIstituto Bio Ita Spa; Aurobindo Pharma; Sandoz; Antibiotice; Sagent Pharms; Agila Speclts

4 of 4  
Drug NameNallpen in plastic container
Active IngredientNafcillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/100ml; eq 20mg base/ml
Market StatusPrescription
CompanyBaxter Hlthcare

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]

API Reference Price

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09-Feb-2021
30-Oct-2024
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