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Details

Stereochemistry ACHIRAL
Molecular Formula C9H9NO3
Molecular Weight 179.1727
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACEDOBEN

SMILES

CC(=O)NC1=CC=C(C=C1)C(O)=O

InChI

InChIKey=QCXJEYYXVJIFCE-UHFFFAOYSA-N
InChI=1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)

HIDE SMILES / InChI

Molecular Formula C9H9NO3
Molecular Weight 179.1727
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2431857

Acedoben (4-acetamidobenzoic acid) is a benzoic acid derivative and a metabolite of benzocaine. It is a component of immunomodulatory drug inosine pranobex, which is used to treat mucocutaneous infections due to herpes simplex virus (type 1 and/or type II), genital warts as adjunctive therapy to podophyllin or carbon dioxide laser, and subacute sclerosing panencephalitis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
IMUNOVIR

Approved Use

Imunovir tablets are indicated in the management of mucocutaneous infections due to herpes simplex virus (type 1 and/or type II), genital warts as adjunctive therapy to podophyllin or carbon dioxide laser, and subacute sclerosing panencephalitis.

Launch Date

1983
Primary
IMUNOVIR

Approved Use

Imunovir tablets are indicated in the management of mucocutaneous infections due to herpes simplex virus (type 1 and/or type II), genital warts as adjunctive therapy to podophyllin or carbon dioxide laser, and subacute sclerosing panencephalitis.

Launch Date

1983
Primary
IMUNOVIR

Approved Use

Imunovir tablets are indicated in the management of mucocutaneous infections due to herpes simplex virus (type 1 and/or type II), genital warts as adjunctive therapy to podophyllin or carbon dioxide laser, and subacute sclerosing panencephalitis.

Launch Date

1983
PubMed

PubMed

TitleDatePubMed
Inosine pranobex. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.
1986 Nov
Inhibition of Pneumocystis carinii dihydropteroate synthetase by para-acetamidobenzoic acid: possible mechanism of action of isoprinosine in human immunodeficiency virus infection.
1993 Jun
Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design.
1997 Dec 5
Quantification of benzocaine and its metabolites in channel catfish tissues and fluids by HPLC.
1997 Sep
Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies).
2002 May
Metabolites of a blocked chloramphenicol producer.
2003 Jan
Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase.
2005 Apr 1
Separate coding of different gaze directions in the superior temporal sulcus and inferior parietal lobule.
2007 Jan 9
Simultaneous determination of p-aminobenzoic acid and its metabolites in the urine of volunteers, treated with p-aminobenzoic acid sunscreen formulation.
2007 Mar 12
Individual differences in Scanpaths correspond with serotonin transporter genotype and behavioral phenotype in rhesus monkeys (Macaca mulatta).
2009
The human brain in numbers: a linearly scaled-up primate brain.
2009
General intelligence in another primate: individual differences across cognitive task performance in a New World monkey (Saguinus oedipus).
2009 Jun 17
Prognostic value of N-terminal pro-brain natriuretic peptide in elderly people with acute myocardial infarction: prospective observational study.
2009 May 6
Rhesus monkeys' valuation of vocalizations during a free-choice task.
2009 Nov 18
Ambiguity aversion in rhesus macaques.
2010
Striatal BOLD Response Reflects the Impact of Herd Information on Financial Decisions.
2010
Following gaze: gaze-following behavior as a window into social cognition.
2010
Coordinated scaling of cortical and cerebellar numbers of neurons.
2010
Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P.
2010 May
Immunomodulatory effects of inosine pranobex on cytokine production by human lymphocytes.
2015 Jun
Patents

Sample Use Guides

Mucocutaneous herpes simplex: 1 g q.d.s. (4g daily), for 7 -14 days. Genital warts: 1g t.d.s. (3g daily), for 14-28 days as adjunctive therapy to podophyllin or carbon dioxide laser. Subacute sclerosing panencephalitis (SSPE): 50-100mg/kg daily, in divided does every 4 hours.
Route of Administration: Oral
In Vitro Use Guide
Inosine pranobex has been shown to stimulate various indices of metabolic activity of macrophages and monocytes. In vitro exposure to inosine pranobex or to 24-hour supernatants obtained from mononuclear cells pretreated with the drug restored chemotaxis to normal or near normal levels. Incubation with inosine pranobex in vitro stimulated the production of interleukin-l (lymphocyte activating factor) in human monocytes.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:50:37 GMT 2023
Edited
by admin
on Sat Dec 16 17:50:37 GMT 2023
Record UNII
04Z20NMK31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACEDOBEN
INN   MART.   WHO-DD  
INN  
Official Name English
NSC-4002
Code English
acedoben [INN]
Common Name English
P-ACETAMIDOBENZOIC ACID
Common Name English
Acedoben [WHO-DD]
Common Name English
ACEDOBEN [MART.]
Common Name English
4-ACETAMIDOBENZOIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C73539
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
209-114-7
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL112687
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
NSC
4002
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
WIKIPEDIA
ACEDOBEN
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
EVMPD
SUB05203MIG
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
NCI_THESAURUS
C74109
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID5024392
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
DRUG BANK
DB04500
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
CAS
556-08-1
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
PUBCHEM
19266
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
FDA UNII
04Z20NMK31
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
CHEBI
46171
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
SMS_ID
100000087909
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
INN
4688
Created by admin on Sat Dec 16 17:50:38 GMT 2023 , Edited by admin on Sat Dec 16 17:50:38 GMT 2023
PRIMARY
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ACTIVE MOIETY