An official website of the United States government

(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride

PubChem CID
16051971
Structure
(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride_small.png
(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride_3D_Structure.png
Molecular Formula
Synonyms
  • Ethambutol Hydrochloride
  • Ethambutol dihydrochloride
  • 1070-11-7
  • (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride
  • SCHEMBL3398
Molecular Weight
240.77 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Parent Compound
Dates
  • Create:
    2007-05-07
  • Modify:
    2024-12-14
Description

Ethambutol hydrochloride is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of active tuberculosis (TB) of the lungs. (Active TB is also called TB disease.)

TB can be an opportunistic infection (OI) of HIV.

Ethambutol Hydrochloride is the hydrochloride salt form of ethambutol, an ethylenediamine derivative with antibacterial activity, specifically effective against mycobacteria. Although the exact mechanism of action of ethambutol hydrochloride is unknown, ethambutol hydrochloride inhibits the transfer of mycolic acids into the cell wall of bacteria, which impedes bacterial cell growth. This agent may also interfere with RNA synthesis or inhibit other cell metabolism, thereby preventing cell multiplication and causing cell death.
An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)
See also: Ethambutol Hydrochloride (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;hydrochloride
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C10H24N2O2.ClH/c1-3-9(7-13)11-5-6-12-10(4-2)8-14;/h9-14H,3-8H2,1-2H3;1H/t9-,10-;/m0./s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

ZVRRAFGIXXGENK-IYPAPVHQSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CC[C@@H](CO)NCCN[C@@H](CC)CO.Cl
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

2.2 Molecular Formula

C10H25ClN2O2
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

1070-11-7

2.3.2 European Community (EC) Number

2.3.3 ChEMBL ID

2.3.4 KEGG ID

2.3.5 Metabolomics Workbench ID

2.3.6 NCI Thesaurus Code

2.3.7 NSC Number

2.3.8 RXCUI

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Dexambutol
  • EMB Fatol
  • EMB Hefa
  • EMB-Fatol
  • EMB-Hefa
  • Etambutol Llorente
  • Ethambutol
  • Ethambutol Hydrochloride
  • Etibi
  • Hydrochloride, Ethambutol
  • Llorente, Etambutol
  • Miambutol
  • Myambutol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
240.77 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
240.1604557 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
240.1604557 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
64.5Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
109
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
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 2019.01.04)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Human drug -> Prescription; Discontinued; Active ingredient (ETHAMBUTOL HYDROCHLORIDE)

5 Chemical Vendors

6 Drug and Medication Information

6.1 FDA Approved Drugs

6.2 FDA Orange Book

6.3 FDA National Drug Code Directory

6.4 Drug Labels

Drug and label
Active ingredient and drug

6.5 HIV / AIDS and Opportunistic Infection Drugs

What is Ethambutol Hydrochloride

Ethambutol hydrochloride is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of active tuberculosis (TB) of the lungs. (Active TB is also called TB disease.)

TB can be an opportunistic infection (OI) of HIV.

Drug Class
Antimycobacterials

6.6 Clinical Trials

6.6.1 ClinicalTrials.gov

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Antitubercular Agents
Drugs used in the treatment of tuberculosis. They are divided into two main classes: first-line agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and second-line drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)

7.2 FDA Pharmacological Classification

Non-Proprietary Name
ETHAMBUTOL HYDROCHLORIDE
Pharmacological Classes
Antimycobacterial [EPC]

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

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

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Health Hazard
Signal
Danger
GHS Hazard Statements
H360 (97.7%): May damage fertility or the unborn child [Danger Reproductive toxicity]
Precautionary Statement Codes

P203, P280, P318, 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 44 reports by companies from 5 notifications to the ECHA C&L Inventory.

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.

9.1.2 Hazard Classes and Categories

Repr. 1A (97.7%)

9.2 Other Safety Information

Chemical Assessment

IMAP assessments - 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, dihydrochloride, [S-(R*,R*)]-: Environment tier I assessment

IMAP assessments - 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, dihydrochloride, [S-(R*,R*)]-: Human health tier I assessment

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEMBL Target Tree

13.3 UN GHS Classification

13.4 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, dihydrochloride, [S-(R*,R*)]-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. DTP/NCI
    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
  4. 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
    [S-(R*,R*)]-2,2'-(ethylenediimino)dibutan-1-ol dihydrochloride
    https://echa.europa.eu/substance-information/-/substanceinfo/100.012.701
    [S-(R*,R*)]-2,2'-(ethylenediimino)dibutan-1-ol dihydrochloride (EC: 213-970-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/667
  5. ChEMBL
    LICENSE
    Access 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
  6. 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
  7. DailyMed
  8. Drug Database, Clinicalinfo.hiv.gov
    LICENSE
    Unless otherwise noted, material presented on the HIV.gov website is considered Federal government information and is in the public domain. That means this information may be freely copied and distributed. We request that you use appropriate attribution to HIV.gov.
    https://www.hiv.gov/about-us/mission-and-team
  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. 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
  11. 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
  12. 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
  13. Metabolomics Workbench
  14. 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
  15. 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
  16. Springer Nature
  17. 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
  18. PubChem
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS