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Phenytoin Sodium

PubChem CID
657302
Structure
Phenytoin Sodium_small.png
Phenytoin Sodium_3D_Structure.png
Molecular Formula
Synonyms
  • PHENYTOIN SODIUM
  • 630-93-3
  • 5,5-Diphenylhydantoin sodium salt
  • Dilantin sodium
  • Sodium phenytoin
Molecular Weight
274.25 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Dates
  • Create:
    2005-06-29
  • Modify:
    2025-01-11
Description
Diphenylhydantoin (Phenytoin), Sodium Salt can cause cancer according to an independent committee of scientific and health experts.
Phenytoin Sodium is the sodium salt form of phenytoin, a hydantoin derivate and non-sedative antiepileptic agent with anticonvulsant activity. Phenytoin sodium promotes sodium efflux from neurons located in the motor cortex, thereby stabilizing the neuron and inhibiting synaptic transmission. This leads to a reduction in posttetanic potentiation at synapses, an inhibition of repetitive firing of action potentials and ultimately inhibits the spread of seizure activity.
An anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Phenytoin Sodium.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;5,5-diphenylimidazolidin-3-ide-2,4-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H12N2O2.Na/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12;/h1-10H,(H2,16,17,18,19);/q;+1/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

FJPYVLNWWICYDW-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C(C=C1)C2(C(=O)[N-]C(=O)N2)C3=CC=CC=C3.[Na+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H11N2NaO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

630-93-3

2.3.2 Deprecated CAS

1421-15-4, 143-75-9, 8017-52-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 NCI Thesaurus Code

2.3.8 RXCUI

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,5-Diphenylhydantoin
  • 5,5-diphenylimidazolidine-2,4-dione
  • Antisacer
  • Difenin
  • Dihydan
  • Dilantin
  • Diphenylhydantoin
  • Diphenylhydantoinate, Sodium
  • Epamin
  • Epanutin
  • Fenitoin
  • Hydantol
  • Phenhydan
  • Phenytoin
  • Phenytoin Sodium
  • Sodium Diphenylhydantoinate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
274.25 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
274.07182188 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
274.07182188 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
47.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
356
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
0
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
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Collision Cross Section

158.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Prescription; Discontinued; Active ingredient (PHENYTOIN SODIUM)
Human drug -> Discontinued
Human drug -> Prescription; Discontinued
Human drug -> Prescription
3.3.1.2 Animal Drugs
Active Ingredients (Phenytoin Sodium) -> FDA Greenbook

4 Spectral Information

4.1 IR Spectra

4.1.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sun Pharmaceutical Industries Ltd.
Catalog Number
prescription
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA Medication Guides

Drug
Active Ingredient
PHENYTOIN SODIUM
Form;Route
CAPSULE;ORAL
Company
UPJOHN
Date
9/7/22
Drug
Active Ingredient
PHENYTOIN
Form;Route
TABLET, CHEWABLE;ORAL
Company
PHARMACIA
Date
10/22/21

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 FDA National Drug Code Directory

7.5 FDA Green Book

7.6 Drug Labels

Drug and label
Drug and label
Active ingredient and drug

7.7 Clinical Trials

7.7.1 ClinicalTrials.gov

7.7.2 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Anticonvulsants
Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)
Cytochrome P-450 CYP1A2 Inducers
Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inducers.)
Voltage-Gated Sodium Channel Blockers
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)

8.2 FDA Pharmacological Classification

1 of 2
Non-Proprietary Name
EXTENDED PHENYTOIN SODIUM
Pharmacological Classes
Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2C9 Inducers [MoA]; Anti-epileptic Agent [EPC]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2D6 Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]
2 of 2
Non-Proprietary Name
PHENYTOIN SODIUM
Pharmacological Classes
Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 2C8 Inducers [MoA]; Anti-epileptic Agent [EPC]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Cytochrome P450 2D6 Inducers [MoA]

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
2,4-Imidazolidinedione, 5,5-diphenyl-, sodium salt (1:1): ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H301 (18.8%): Toxic if swallowed [Danger Acute toxicity, oral]

H302 (81.2%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (82.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H351 (78.1%): Suspected of causing cancer [Warning Carcinogenicity]

H360 (15.6%): May damage fertility or the unborn child [Danger Reproductive toxicity]

H361 (83.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H372 (18.2%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Precautionary Statement Codes

P203, P260, P261, P264, P270, P272, P280, P301+P316, P301+P317, P302+P352, P318, P319, P321, P330, P333+P317, P362+P364, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 192 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (18.8%)

Acute Tox. 4 (81.2%)

Skin Sens. 1 (82.8%)

Carc. 2 (78.1%)

Repr. 1B (15.6%)

Repr. 2 (83.3%)

STOT RE 1 (18.2%)

10.2 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Carcinogenicity

Authoritative List - NTP RoC - reasonable; Prop 65

Report - regardless of intended function of ingredient in the product

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Phenytoin sodium: Does not have an individual approval but may be used under an appropriate group standard

10.3 Other Safety Information

Chemical Assessment

IMAP assessments - 2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt: Human health tier I assessment

IMAP assessments - 2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt: Environment tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 Chemical Co-Occurrences in Patents

13.3 Chemical-Disease Co-Occurrences in Patents

13.4 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 ChemIDplus

16.4 UN GHS Classification

16.5 CCSBase Classification

16.6 EPA DSSTox Classification

16.7 EPA TSCA and CDR Classification

16.8 FDA Drug Type and Pharmacologic Classification

16.9 EPA Substance Registry Services Tree

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt
    https://services.industrialchemicals.gov.au/search-assessments/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    2,4-Imidazolidinedione, 5,5-diphenyl-, sodium salt (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless 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
  7. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. California Office of Environmental Health Hazard Assessment (OEHHA)
  9. NCI Thesaurus (NCIt)
    LICENSE
    Unless 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-reuse
  10. California Safe Cosmetics Program (CSCP) Product Database
  11. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  12. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  13. DailyMed
  14. Drug Gene Interaction database (DGIdb)
    LICENSE
    The 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/downloads
  15. Drugs@FDA
    LICENSE
    Unless 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
  16. EU Clinical Trials Register
  17. FDA Approved Animal Drug Products (Green Book)
    LICENSE
    Unless 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
  18. FDA Orange Book
    LICENSE
    Unless 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
  19. FDA Medication Guides
    LICENSE
    Unless 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
  20. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  21. National Drug Code (NDC) Directory
    LICENSE
    Unless 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
  22. NLM RxNorm Terminology
    LICENSE
    The 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.html
  23. SpectraBase
  24. Springer Nature
  25. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  26. Wikidata
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works 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.html
    Cytochrome P-450 CYP1A2 Inducers
    https://www.ncbi.nlm.nih.gov/mesh/68065694
    Voltage-Gated Sodium Channel Blockers
    https://www.ncbi.nlm.nih.gov/mesh/68061567
  28. PubChem
  29. GHS Classification (UNECE)
  30. EPA Substance Registry Services
  31. NCBI
CONTENTS