DIMEPRANOL ACEDOBEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H9NO3.C5H13NO
Molecular Weight	282.3355
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FJFQBKRMSCKTSE-UHFFFAOYSA-N

InChI=1S/C9H9NO3.C5H13NO/c1-6(11)10-8-4-2-7(3-5-8)9(12)13;1-5(7)4-6(2)3/h2-5H,1H3,(H,10,11)(H,12,13);5,7H,4H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C5H13NO
Molecular Weight	103.1628
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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
Sources: https://www.medicines.org.uk/emc/medicine/27089
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

Primary Target	Pharmacology	Condition	Potency
immune response 6 Target ID: GO:0006955 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2431857	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Herpes simplex infection 28 Sources: https://www.medicines.org.uk/emc/medicine/27089	Primary	Approved 8583	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
Genital warts 9 Sources: https://www.medicines.org.uk/emc/medicine/27089	Primary	Approved 8583	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
Subacute sclerosing panencephalitis 4 Sources: https://www.medicines.org.uk/emc/medicine/27089	Primary	Approved 8583	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

Title	Date	PubMed
Immunomodulatory effects of inosine pranobex on cytokine production by human lymphocytes.	2015-06	26011933
Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P.	2010-05	20131080
Ambiguity aversion in rhesus macaques.	2010	20922060
Striatal BOLD Response Reflects the Impact of Herd Information on Financial Decisions.	2010	20589242
Following gaze: gaze-following behavior as a window into social cognition.	2010	20428494
Coordinated scaling of cortical and cerebellar numbers of neurons.	2010	20300467
Rhesus monkeys' valuation of vocalizations during a free-choice task.	2009-11-18	19924223
General intelligence in another primate: individual differences across cognitive task performance in a New World monkey (Saguinus oedipus).	2009-06-17	19536274
Prognostic value of N-terminal pro-brain natriuretic peptide in elderly people with acute myocardial infarction: prospective observational study.	2009-05-06	19420032
Individual differences in Scanpaths correspond with serotonin transporter genotype and behavioral phenotype in rhesus monkeys (Macaca mulatta).	2009	19949466
The human brain in numbers: a linearly scaled-up primate brain.	2009	19915731
Simultaneous determination of p-aminobenzoic acid and its metabolites in the urine of volunteers, treated with p-aminobenzoic acid sunscreen formulation.	2007-03-12	17118613
Separate coding of different gaze directions in the superior temporal sulcus and inferior parietal lobule.	2007-01-09	17208181
Ketoprofen-inhibited N-acetyltransferase activity and gene expression in human colon tumor cells.	2006-04-20	16619513
Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase.	2005-04-01	15755666
PCR and flow cytometric analysis of paclitaxel-inhibited arylamine N-acetyltransferase activity and gene expression in human osteogenic sarcoma cells (U-2 OS).	2004-03-16	15015580
Metabolites of a blocked chloramphenicol producer.	2003-01	12542347
Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies).	2002-05	12118261
Contribution of hydrogen bonding to protein stability estimated from isotope effects.	2002-02-19	11841202
Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamine N-acetyltransferase activity in human bladder tumour cells.	2002-01-25	11807928
[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].	2001-08	11602060
Effects of the butylated hydroxyanisole and butylated hydroxytoluene on the DNA adduct formation and arylamines N-acetyltransferase activity in human colon tumor cells.	2001-06-09	11396144
Ellagic acid inhibited 2-aminofluorene and p-aminobenzoic acid acetylation by mononuclear leucocytes from Sprague-Dawley rats.	2001	11258539
Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design.	1997-12-05	9406595
Quantification of benzocaine and its metabolites in channel catfish tissues and fluids by HPLC.	1997-09	9447553
Inhibition of Pneumocystis carinii dihydropteroate synthetase by para-acetamidobenzoic acid: possible mechanism of action of isoprinosine in human immunodeficiency virus infection.	1993-06	7687120
Inosine pranobex. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.	1986-11	2431857

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:18:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:55 GMT 2025`
Record UNII	1V339IMQ38
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMEPRANOL ACEDOBEN

Official Name

English

(±)-1-(DIMETHYLAMINO)-2-PROPANOL, P-ACETAMIDOBENZOATE (SALT)

Preferred Name

English

DIMEPRANOL ACEDOBEN [USAN]

Common Name

English

DIMEPRANOL-4-ACETAMIDOBENZOATE

Common Name

English

2-PROPANOL, 1-(DIMETHYLAMINO)-, (±)-, 4-(ACETYLAMINO)BENZOATE (SALT)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308