U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H22O4
Molecular Weight 302.3649
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MASOPROCOL

SMILES

C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC2=CC=C(O)C(O)=C2

InChI

InChIKey=HCZKYJDFEPMADG-TXEJJXNPSA-N
InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+

HIDE SMILES / InChI

Description

Misoprostol is an antineoplastic drug used to treat skin growths caused by sun exposure. Masoprocol is a novel antineoplastic agent was used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated). Masoprocol was withdrawn from the U.S. market in June 1996. It is not known exactly how Masoprocol works. Studies have shown that masoprocol is a potent 5-lipoxygenase inhibitor and has antiproliferative activity against keratinocytes in tissue culture, but the relationship between this activity and its effectiveness in actinic keratoses is unknown. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known. Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACTINEX
PubMed

PubMed

TitleDatePubMed
Low-density lipoprotein induced actin cytoskeleton reorganization in endothelial cells: mechanisms of action.
2001
Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2).
2001
Johns Hopkins embroiled in fresh misconduct allegations.
2001 Aug 2
Pharmacological modulation of allergic inflammation in the rat airways and association with mast cell heterogeneity.
2001 Aug 24
Nordihydroguaiaretic acid elevates osteoblastic intracellular Ca2+.
2001 Dec
Determination of binding constant of transcription factor AP-1 and DNA. Application of inhibitors.
2001 Feb
Fatty acids inhibit anion secretion in rat colon: apical and basolateral action sites.
2001 Jul
Biocompatibility of NDGA-polymerized collagen fibers. II. Attachment, proliferation, and migration of tendon fibroblasts in vitro.
2001 Jul
Baicalein protects cortical neurons from beta-amyloid (25-35) induced toxicity.
2001 Jul 20
Effect of nordihydroguaiaretic acid on behavioral impairment and neuronal cell death after forebrain ischemia.
2001 Jul-Aug
Arachidonic acid stimulates glucose uptake in 3T3-L1 adipocytes by increasing GLUT1 and GLUT4 levels at the plasma membrane. Evidence for involvement of lipoxygenase metabolites and peroxisome proliferator-activated receptor gamma.
2001 Mar 23
Mechanisms of cytokine-induced death of cultured bovine luteal cells.
2001 May
Arachidonic acid modulates the spatiotemporal characteristics of agonist-evoked Ca2+ waves in mouse pancreatic acinar cells.
2001 May 18
Intracellular signaling pathway of FGF-2-modulated corneal endothelial cell migration during wound healing in vitro.
2001 Nov
Lipoxygenase inhibitors inhibit heparin-releasable lipoprotein lipase activity in 3T3-L1 adipocytes and enhance body fat reduction in mice by conjugated linoleic acid.
2001 Nov 30
Elevating dietary salt exacerbates hyperpnea-induced airway obstruction in guinea pigs.
2001 Sep
Differential role of cytosolic phospholipase A2 in the invasion of brain microvascular endothelial cells by Escherichia coli and Listeria monocytogenes.
2001 Sep 15
tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo.
2001 Sep 28
[Features of lipoxygenase from cells of Mortierella species mushrooms].
2001 Sep-Oct
[Effect of exogenous leukotrienes and lipoxygenase inhibitors on apoptosis and necrosis in cultured rat hepatocytes].
2002
Mechanisms of nordihydroguaiaretic acid-induced growth inhibition and apoptosis in human cancer cells.
2002 Apr 8
Kinetics of inhibition of leukocyte 12-lipoxygenase by the isoform-specific inhibitor 4-(2-oxapentadeca-4-yne)phenylpropanoic acid.
2002 Aug 13
Neurons overexpressing mutant presenilin-1 are more sensitive to apoptosis induced by endoplasmic reticulum-Golgi stress.
2002 Aug 15
Native LDL induces proliferation of human vascular smooth muscle cells via redox-mediated activation of ERK 1/2 mitogen-activated protein kinases.
2002 Feb
Multiple biological effects of inhibitors of arachidonic acid metabolism on human keratinocytes.
2002 Feb
Differential effect of brefeldin A on the palmitoylation of surfactant protein C proprotein mutants.
2002 Jan 11
Evidence for the involvement of cyclooxygenase activity in the development of cocaine sensitization.
2002 Jan-Feb
Nordihydroguaiaretic acid-mediated inhibition of ultraviolet B-induced activator protein-1 activation in human keratinocytes.
2002 Jun
Structure-activity relationship studies of nordihydroguaiaretic acid inhibitors toward soybean, 12-human, and 15-human lipoxygenase.
2002 Jun 6
Effects of various reactive oxygen species on the guinea pig trachea and its epithelium.
2002 Mar
Expression and induction of the stress protein alpha-B-crystallin in vascular endothelial cells.
2002 Mar
Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols.
2002 Mar 15
Comparative quantitative structure toxicity relationships for flavonoids evaluated in isolated rat hepatocytes and HeLa tumor cells.
2002 Mar 20
Involvement of glycogen synthase kinase-3beta and tau phosphorylation in neuronal Golgi disassembly.
2002 May
Contractile response to a cannabimimetic eicosanoid, 2-arachidonoylglycerol, of longitudinal smooth muscle from the guinea-pig distal colon in vitro.
2002 May 31
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.
2002 May 31
Establishment of a first-order kinetic model of light chain-associated amyloid fibril extension in vitro.
2002 Nov 19
Investigation of the role of lipoxygenase in bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung.
2002 Oct
Contribution of different phospholipases and arachidonic acid metabolites in the response of gallbladder smooth muscle to cholecystokinin.
2002 Oct 1
Effect of nordihydroguaiaretic acid on the secretion of lipoprotein lipase.
2002 Sep 30
Patents

Sample Use Guides

In Vivo Use Guide
Apply to lesions b.i.d. for 14–28 d
Route of Administration: Topical
In Vitro Use Guide
Incubation of masoprocol (50 uM) with adipocytes from chow-fed rats significantly inhibited isoproterenol-induced lipolytic activity and HSL activity, associated with a decrease in the ability of isoproterenol to phosphorylate HSL. Masoprocol had no apparent effect on adipose tissue phosphatidylinositol 3-kinase activity, but okadaic acid, a serine/threonine phosphatase inhibitor, blocked the antilipolytic effect of masoprocol.
Name Type Language
MASOPROCOL
INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
INSM18
Common Name English
MESO-4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL
Common Name English
MASOPROCOL [MART.]
Common Name English
ACTINEX
Brand Name English
1,2-BENZENEDIOL, 4,4'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-, (R*,S*)-
Common Name English
NSC-4291
Code English
NORDIHYDROGUAIARETIC ACID [MI]
Common Name English
INSM-18
Common Name English
ORISTAR NHGA
Brand Name English
DIHYDRONORGUAIARETIC ACID
Common Name English
MESO-NDGA
Code English
NDGA
Common Name English
CHX-100
Code English
NSC-682984
Code English
MASOPROCOL [VANDF]
Common Name English
MASOPROCOL [USAN]
Common Name English
4-((2R,3S)-4-(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTYL)BENZENE-1,2-DIOL
Systematic Name English
NORDIHYDROGUAIARETIC ACID [INCI]
Common Name English
MASOPROCOL [INN]
Common Name English
MESO-NORDIHYDROGUAIARETIC ACID
Common Name English
NORDIHYDROGUAIARETIC ACID [WHO-DD]
Common Name English
MASOPROCOL [WHO-DD]
Common Name English
1,2-BENZENEDIOL, 4,4'-((2R,3S)-2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-, REL-
Systematic Name English
MASOPROCOL [ORANGE BOOK]
Common Name English
DINORGUAIARETIC ACID, DIHYDRO-
Common Name English
1,2-BENZENEDIOL, 4,4'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-
Systematic Name English
1,4-BIS(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTANE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
NCI_THESAURUS C1322
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
WHO-VATC QL01XX10
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
CFR 21 CFR 189.165
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
WHO-ATC L01XX10
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
Code System Code Type Description
WIKIPEDIA
NORDIHYDROGUAIARETIC ACID
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
RXCUI
227239
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY RxNorm
EVMPD
SUB08652MIG
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
CAS
500-38-9
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
NON-SPECIFIC STEREOCHEMISTRY
IUPHAR
4265
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
207-903-0
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
ALTERNATIVE
CAS
27686-84-6
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
248-606-6
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
MESH
D009637
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
NCI_THESAURUS
C701
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
PUBCHEM
71398
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
INN
6615
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
MERCK INDEX
M8052
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL3545025
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
EPA CompTox
500-38-9
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
DRUG BANK
DB00179
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY
ChEMBL
CHEMBL52
Created by admin on Tue Oct 22 00:15:55 UTC 2019 , Edited by admin on Tue Oct 22 00:15:55 UTC 2019
PRIMARY