Nafcillin sodium monohydrate
PubChem CID
23704143
Structure
Molecular Formula
Synonyms
- 7177-50-6
- Nafcillin sodium monohydrate
- Nafcillin sodium salt monohydrate
- NAFCILLIN SODIUM
- Unipen
Molecular Weight
454.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Component Compounds
Dates
- Create:2008-02-05
- Modify:2025-01-18
Description
Nafcillin sodium monohydrate is an organic sodium salt and a hydrate. It contains a nafcillin sodium.
Nafcillin Sodium is the sodium salt form of nafcillin, a semi-synthetic naphthalene, penicillin-related Nafcillin inhibits bacterial wall synthesis by a mechanism of action similar to penicillin. Penicillinase-resistant Nafcillin is used to treat infections caused by penicillin-resistant strains of Staphylococci. (NCI04)
NAFCILLIN SODIUM is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1965 and is indicated for infection and has 1 investigational indication.
Chemical Structure Depiction
3D Conformer of Parent
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;hydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C21H22N2O5S.Na.H2O/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);;1H2/q;+1;/p-1/t15-,16+,19-;;/m1../s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
OCXSDHJRMYFTMA-KMFBOIRUSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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-].O.[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C21H23N2NaO6S
Computed by PubChem 2.2 (PubChem release 2021.10.14)
7177-50-6
985-16-0
- Nafcil
- Nafcillin
- Nafcillin Sodium
- Nafcillin, Monosodium Salt, Anhydrous
- Nafcillin, Sodium
- Naphthamidopenicillin
- Sodium Nafcillin
- Sodium, Nafcillin
- 7177-50-6
- Nafcillin sodium monohydrate
- Nafcillin sodium salt monohydrate
- NAFCILLIN SODIUM
- Unipen
- Nafcillin sodium hydrate
- Nafcil
- Nallpen
- Sodium Nafcillin Monohydrate
- Nafcillin (sodium monohydrate)
- Wy 3277
- MFCD01941128
- WY-3277
- DTXSID7045570
- CHEBI:51919
- 49G3001BCK
- 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;hydrate
- NCGC00017070-01
- CAS-7177-50-6
- NSC-757108
- DTXCID5025570
- Nafcillin sodium salt anhydrous
- NAFCILLIN SODIUM [MART.]
- Monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrate
- NAFCILLIN SODIUM [USP-RS]
- SMR000653476
- NAFCILLIN SODIUM [USP MONOGRAPH]
- Nafcillin sodium [USAN]
- Nafcillin natrium-1-wasser
- NAFCILLIN SODIUM MONOHYDRATE [MART.]
- Naphthicillin
- UNII-49G3001BCK
- Nafcillin sodium [USAN:USP]
- Monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrate
- Unipen (TN)
- Nafcillin sodium (USP)
- 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, MONOHYDRATE, (2S,5R,6R)-
- 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, monohydrate, (2S-(2alpha,5alpha,6beta))
- SCHEMBL65687
- MLS001077264
- MLS002222166
- 985-16-0 (anhydrous)
- HY-B0555AR
- 147-52-4 (free acid)
- Nafcillin sodium salt monohydrat
- CHEMBL1568276
- NAFCILLIN SODIUM [VANDF]
- HY-B0555A
- HMS1570J07
- HMS2097J07
- HMS2233C12
- HMS3714J07
- 1ST5640A
- BCP17430
- Tox21_110767
- s4042
- AKOS025402388
- NAFCILLIN SODIUM [ORANGE BOOK]
- Tox21_110767_1
- AC-8800
- CCG-220843
- CCG-269279
- NSC 757108
- NCGC00273482-01
- DA-75972
- Nafcillin (sodium monohydrate) (Standard)
- Nafcillin sodium microg/mL in Acetonitrile
- NAFCILLIN SODIUM MONOHYDRATE [VANDF]
- NAFCILLIN SODIUM MONOHYDRATE [WHO-DD]
- NAFCILLIN SODIUM SALT MONOHYDRATE [MI]
- D00928
- D82069
- 6-(2-Ethoxy-1-naphthamido)penicillin monohydrate
- Q27122988
- Nafcillin sodium monohydrate 100 microg/mL in Acetonitrile
- monohydrate of sodium salt of 6-(2-ethoxy-1-naphthamido)penicillanic acid
- sodium 6beta-[(2-ethoxy-1-naphthoyl)amino]-2,2-dimethylpenam-3alpha-carboxylate hydrate
- (2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt
- 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, MONOHYDRATE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))
- 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, monohydrate, (2S-(2alpha,5alpha,6beta))-
- 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 hydrate
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
454.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
454.11745191 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
454.11745191 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
125 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
705
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Human drug -> Discontinued
Human drug -> Prescription; Discontinued; Active ingredient (NAFCILLIN SODIUM)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
- Nafcillin Sodium (annotation moved to)
- 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, sodium salt, hydrate (1:1:1), (2S,5R,6R)- (annotation moved to)
PubMed Count
Drug and label
Active ingredient and drug
Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
Non-Proprietary Name
NAFCILLIN SODIUM
Pharmacological Classes
Penicillin-class Antibacterial [EPC]; Penicillins [CS]
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
New Zealand EPA Inventory of Chemical Status
Nafcillin sodium: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
- ChEBINafcillin sodium monohydratehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51919
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licenceNAFCILLIN SODIUMhttps://platform.opentargets.org/drug/CHEMBL1568276
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- ChemIDplusNafcillin sodium [USAN:USP]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0007177506ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxNafcillin sodium monohydratehttps://comptox.epa.gov/dashboard/DTXSID7045570CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingNAFCILLIN SODIUMhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/49G3001BCK
- New Zealand Environmental Protection Authority (EPA)LICENSEThis work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.https://www.epa.govt.nz/about-this-site/general-copyright-statement/
- DailyMed
- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsNAFCILLIN SODIUMhttps://www.dgidb.org/drugs/rxcui:9893
- Drugs@FDALICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingNAFCILLIN SODIUMhttps://www.accessdata.fda.gov/scripts/cder/daf/
- FDA Orange BookLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlUSP drug classificationhttp://www.genome.jp/kegg-bin/get_htext?br08302.kegAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegAntiinfectiveshttp://www.genome.jp/kegg-bin/get_htext?br08307.keg
- National Drug Code (NDC) DirectoryLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- NLM RxNorm TerminologyLICENSEThe RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.htmlnafcillin sodiumhttps://rxnav.nlm.nih.gov/id/rxnorm/9893
- Wikidatanafcillin sodium hydratehttps://www.wikidata.org/wiki/Q27122988
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAnti-Bacterial Agentshttps://www.ncbi.nlm.nih.gov/mesh/68000900
- PubChem
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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