ChemFOnt: Showing chemical card for Ethambutol (CFc000008856)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:48 UTC

Chemfont ID

CFc000008856

Molecule Identification

Common Name

Ethambutol

Definition

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)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-2,2'-(Ethylenediimino)di-1-butanol	ChEBI
(+)-Ethambutol	ChEBI
(+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamine	ChEBI
(+)-S,S-Ethambutol	ChEBI
(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol	ChEBI
(S,S)-Ethambutol	ChEBI
EMB	ChEBI
Etambutol	ChEBI
Ethambutolum	ChEBI
S,S-Ethambutol	ChEBI
Servambutol	Kegg
Aethambutolum	HMDB
D-Ethambutol	HMDB
Etambutolo	HMDB
Ethambutol, racemic mixture	HMDB
Fatol brand OF ethambutol hydrochloride	HMDB
Sanavita brand OF ethambutol hydrochloride	HMDB
Wyeth brand OF ethambutol hydrochloride	HMDB
AHP brand OF ethambutol hydrochloride	HMDB
Hydrochloride, ethambutol	HMDB
ICN brand OF ethambutol hydrochloride	HMDB
Lederle brand OF ethambutol hydrochloride	HMDB
Miambutol	HMDB
EMB hefa	HMDB
EMB-fatol	HMDB
EMB-hefa	HMDB
Etambutol llorente	HMDB
Etibi	HMDB
Genopharm brand OF ethambutol hydrochloride	HMDB
Llorente brand OF ethambutol hydrochloride	HMDB
Myambutol	HMDB
Riemser brand OF ethambutol hydrochloride	HMDB
Dexambutol	HMDB
EMB fatol	HMDB
Elan brand OF ethambutol hydrochloride	HMDB
Ethambutol hydrochloride	HMDB
Llorente, etambutol	HMDB
SERB brand OF ethambutol hydrochloride	HMDB
Wernigerode brand OF ethambutol hydrochloride	HMDB

Chemical Formula

C₁₀H₂₄N₂O₂

Average Molecular Weight

204.3098

Monoisotopic Molecular Weight

204.183778022

IUPAC Name

(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol

Traditional Name

ethambutol

CAS Registry Number

74-55-5

SMILES

CC[C@@H](CO)NCCN[C@@H](CC)CO

InChI Identifier

InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1

InChI Key

AEUTYOVWOVBAKS-UWVGGRQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

1,2-aminoalcohol
Secondary amine
Secondary aliphatic amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ethanolamines (CHEBI:4877 )
ethylenediamine derivative (CHEBI:4877 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014474)
Membrane (HMDB: HMDB0014474)

Source

Exogenous

Exogenous (HMDB: HMDB0014474)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.58 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	-0.059	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	64.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	57.89 m³·mol⁻¹	ChemAxon
Polarizability	24.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon