Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01266)
Name
Nafcillin
Synonyms    Click to Show/Hide the Synonyms of This API
nafcillin; Naphcillin; Nallpen; Nafcilina; Nafcilline; Nafcillinum; Unipen; 147-52-4; (2-Ethoxy-1-naphthyl)penicillin; Nafcilina [INN-Spanish]; Nafcilline [INN-French]; Nafcillinum [INN-Latin]; Nafcillin sodium salt; (2-ethoxy-1-naphthalenyl)penicillin; CHEBI:7447; UNII-4CNZ27M7RV; (2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Penicillin, (2-ethoxy-1-naphthalenyl)-; 6-(2-ethoxy-1-naphthamido)penicillanic acid; 4CNZ27M7RV; Nafcilin-1; Nafcillin [INN:BAN]; (2s,5r,6r)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Nafcillin (INN); 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-; HSDB 3133; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-; 7177-50-6; EINECS 205-690-9; Penicillin, (2-ethoxy-1-naphthyl)-; BRN 0862393; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-; Nafcillin, Antibiotic for Culture Media Use Only; Prestwick0_000843; Prestwick1_000843; Prestwick2_000843; Prestwick3_000843; Epitope ID:141583; CHEMBL1443; SCHEMBL47797; BSPBio_000825; SPBio_002746; BPBio1_000909; DTXSID8023343; GTPL10942; Ethoxynaphthamido Penicillin Sodium; BCP17447; ZINC3875980; BDBM50103525; DB00607; 6beta-(2-ethoxynaphthalene-1-carboxamido)-2,2-dimethylpenam-3alpha-carboxylic acid; (2S,5R,6R)-6-({[2-(ethyloxy)naphthalen-1-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; C07250; D08242; 177N506; Q1638852; W-108115; BRD-K18574842-323-03-3; (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical Status
Approved
PubChem CID
8982
Formula
C21H22N2O5S
Canonical 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
InChI
1S/C21H22N2O5S/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)/t15-,16+,19-/m1/s1
InChIKey
GPXLMGHLHQJAGZ-JTDSTZFVSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=8982"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 414.5 Topological Polar Surface Area 121
XlogP 2.9 Complexity 699
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Nafcillin 2g/100ml solution Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Dextrose Monohydrate; Trisodium Citrate Dihydrate; Hydrochloric Acid; Sodium Hydroxide; Water
                   Dosage Form Solution
                   Company Baxter Healthcare Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [1]
          Nafcillin 1g powder Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium Citrate
                   Dosage Form Powder
                   Company Sagent Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [2]
References
1 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
2 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.

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