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

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 828

Conditions

Condition	Modality	Highest Phase	Product
Herpes simplex infection 28 Sources: https://www.medicines.org.uk/emc/medicine/27089	Primary	Approved 8429	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 14 Sources: https://www.medicines.org.uk/emc/medicine/27089	Primary	Approved 8429	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 8429	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
Inosine pranobex. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.	1986 Nov	2431857
Inhibition of Pneumocystis carinii dihydropteroate synthetase by para-acetamidobenzoic acid: possible mechanism of action of isoprinosine in human immunodeficiency virus infection.	1993 Jun	7687120
Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design.	1997 Dec 5	9406595
Quantification of benzocaine and its metabolites in channel catfish tissues and fluids by HPLC.	1997 Sep	9447553
Effects of the butylated hydroxyanisole and butylated hydroxytoluene on the DNA adduct formation and arylamines N-acetyltransferase activity in human colon tumor cells.	2001 Mar-Apr	11396144
Contribution of hydrogen bonding to protein stability estimated from isotope effects.	2002 Feb 19	11841202
Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamine N-acetyltransferase activity in human bladder tumour cells.	2002 Jan-Feb	11807928
Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies).	2002 May	12118261
Metabolites of a blocked chloramphenicol producer.	2003 Jan	12542347
PCR and flow cytometric analysis of paclitaxel-inhibited arylamine N-acetyltransferase activity and gene expression in human osteogenic sarcoma cells (U-2 OS).	2004 Jan-Feb	15015580
Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase.	2005 Apr 1	15755666
Ketoprofen-inhibited N-acetyltransferase activity and gene expression in human colon tumor cells.	2006 Mar-Apr	16619513
Separate coding of different gaze directions in the superior temporal sulcus and inferior parietal lobule.	2007 Jan 9	17208181
Simultaneous determination of p-aminobenzoic acid and its metabolites in the urine of volunteers, treated with p-aminobenzoic acid sunscreen formulation.	2007 Mar 12	17118613
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
General intelligence in another primate: individual differences across cognitive task performance in a New World monkey (Saguinus oedipus).	2009 Jun 17	19536274
Prognostic value of N-terminal pro-brain natriuretic peptide in elderly people with acute myocardial infarction: prospective observational study.	2009 May 6	19420032
Rhesus monkeys' valuation of vocalizations during a free-choice task.	2009 Nov 18	19924223
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
Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P.	2010 May	20131080
Immunomodulatory effects of inosine pranobex on cytokine production by human lymphocytes.	2015 Jun	26011933

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.

Name

Type

Language

DIMEPRANOL ACEDOBEN

Official Name

English

DIMEPRANOL ACEDOBEN [USAN]

Common Name

English

DIMEPRANOL-4-ACETAMIDOBENZOATE

Common Name

English

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

Common Name

English

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308