Page last updated: 2024-11-04

phenazopyridine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Phenazopyridine is a medication used to relieve the pain, burning, and urgency associated with urinary tract infections. It is not an antibiotic and does not treat the infection itself. Phenazopyridine works by numbing the lining of the urinary tract. It is available over-the-counter (OTC) and by prescription. Phenazopyridine can be synthesized through a series of reactions starting with the condensation of 2-aminopyridine with a substituted benzaldehyde. The resulting Schiff base is then reduced to the corresponding amine, which is then cyclized with a suitable oxidizing agent. The resulting phenazopyridine can then be further functionalized as needed. Studies on phenazopyridine focus on its efficacy and safety, as well as potential interactions with other medications. Its importance lies in its ability to provide symptomatic relief for urinary tract infections, particularly in situations where immediate antibiotic therapy is not feasible or when the infection is mild and self-limiting. Research into phenazopyridine also explores its potential applications in other medical fields, such as its anti-inflammatory properties and its ability to modulate immune responses.'

lapachenole: photoaffinity label [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Phenazopyridine: A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phenazopyridine : A diaminopyridine that is 2,6-diaminopyridine substituted at position 3 by a phenylazo group. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID174859
CHEMBL ID461774
CHEBI ID6376
MeSH IDM0016493
PubMed CID4756
CHEMBL ID1242
CHEMBL ID1355537
CHEMBL ID1625467
CHEBI ID71416
SCHEMBL ID253232
SCHEMBL ID14340038
MeSH IDM0016493

Synonyms (145)

Synonym
lapachenole
573-13-7
C09950
CHEMBL461774 ,
lapachenol
chebi:6376 ,
AC1L5BOW ,
2h-naphtho(1,2-b)pyran, 6-methoxy-2,2-dimethyl-
CTK5A6658 ,
6-methoxy-2,2-dimethyl-2h-benzo[h]chromene
6-methoxy-2,2-dimethyl-benzo[h]chromene
DTXSID20205914
Q27107180
AC-13546
BRD-K76304753-003-05-4
2,6-pyridinediamine, 3-(phenylazo)-
nsc227115
pyridiate
3-[(e)-phenylazo]pyridine-2,6-diamine
2,6-diamino-3-phenylazopyridine, (3e)
2,6-pyridinediamine, 3-[(e)-phenylazo]-
KBIO1_000811
DIVK1C_000811
3-[(e)-phenyldiazenyl]pyridine-2,6-diamine
3-[(e)-phenyldiazenyl]pyridine-2,6-diamine hydrochloride
SPECTRUM_001013
viridium
brn 0184497
urogesic
hsdb 3153
phenazopyridine [inn:ban]
pyridine, 2,6-diamino-3-(phenylazo)-
geridium
nsc 145895
gastrotest
eridium
fenazopiridina [inn-spanish]
einecs 202-363-2
phenazopyridinum [inn-latin]
cas-136-40-3
NCGC00016402-01
BSPBIO_002187
PRESTWICK2_000752
BSPBIO_000764
BPBIO1_000842
SPECTRUM5_001403
IDI1_000811
PRESTWICK3_000752
baridium
94-78-0
phenazopyridine
3-(phenylazo)-2,6-pyridinediamine
C07429
pyridine,6-diamino-3-(phenylazo)-
2,6-diamino-3-(phenylazo)pyridine
wln: t6nj bz cnunr& fz
nsc145895
gastracid
uridinal
pyrazofen
nsc-145895
pyridacil
phenylazo tablet
2, 3-(phenylazo)-
2,6-diamino-3-phenylazopyridine
DB01438
KBIO2_001493
KBIO3_001687
KBIO2_006629
KBIOGR_000948
KBIOSS_001493
KBIO2_004061
SPBIO_000053
SPECTRUM2_000017
NINDS_000811
SPECTRUM3_000544
SPBIO_002703
SPECTRUM4_000474
PRESTWICK1_000752
PRESTWICK0_000752
NCGC00018130-01
CHEMBL1242
AKOS003343059
D08346
phenazopyridine (inn)
fenazopiridina (tn)
3-phenyldiazenylpyridine-2,6-diamine
NCGC00018130-04
NCGC00018130-06
NCGC00091334-04
NCGC00018130-03
NCGC00018130-02
NCGC00018130-05
3-(phenyldiazenyl)pyridine-2,6-diamine
bdbm50420356
FT-0673697
unii-k2j09emj52
5-22-14-00711 (beilstein handbook reference)
k2j09emj52 ,
fenazopiridina
phenazopyridinum
CHEBI:71416 ,
SCHEMBL253232
phenazopyridine [mi]
phenazopyridine [who-dd]
phenazopyridine [hsdb]
phenazopyridine [inn]
phenazopyridine [vandf]
gtpl7616
SCHEMBL14340038
CHEMBL1355537
CHEMBL1625467
urodine (salt/mix)
mallophene (salt/mix)
di-azo (salt/mix)
diridone (salt/mix)
w 1655 (salt/mix)
nc 150 (salt/mix)
pirid (salt/mix)
nefrecil (salt/mix)
mallofeen (salt/mix)
3-[phenyldiazenyl]-2,6-pyridinediamine #
phenazodine (salt/mix)
QPFYXYFORQJZEC-FOCLMDBBSA-N
pyrazodine (salt/mix)
pyridacil (salt/mix)
3-phenylazo-2,6-pyridinediamine
suladyne (salt/mix)
sedural (salt/mix)
uridinal (salt/mix)
HMS3604J12
AB00053519_06
AB00053519_07
DTXSID1023445 ,
AKOS028108443
SBI-0051479.P003
3-(2-phenyldiazen-1-yl)pyridine-2,6-diamine
Q3114549
gastracid;gastrotest;nsc 145895
BRD-K76304753-003-08-8
STARBLD0000241
bdbm430637
CS-0013734
HY-B0985A
EN300-7477352

Research Excerpts

Overview

Phenazopyridine is an azo dye, which exerts local anesthetic or analgesic action on urinary tract mucosa through an unknown mechanism. Phenazopy is a common, well-tolerated medication with minimal side effects. Common side-effects of this drug include, orange discoloration of urine, methemoglobinemia, yellowish skin discolration, hepatitis and acute renal failure.

ExcerptReferenceRelevance
"Phenazopyridine is an azo dye, which exerts local anesthetic or analgesic action on urinary tract mucosa through an unknown mechanism. "( Skin ulcers as a complication of short-term use of phenazopyridine in an old man: A case report.
Elyasi, S; Tavanaee Sani, A; Zarei, B, 2022
)
2.42
"Phenazopyridine is a common, well-tolerated medication with minimal side effects. "( Perioperative Hypoxia Secondary to Phenazopyridine-induced Methemoglobinemia in an Adolescent Patient Without Renal Insufficiency or Overdose: An Unusual Case.
Kraft, KH; Shah, PK, 2019
)
2.23
"Phenazopyridine is a urinary tract analgesic indicated for short-term treatment of irritation in the lower urinary tract. "( Safety analysis of long-term phenazopyridine use for radiation cystitis.
Britnell, SR; Brown, JN; Shore, SN, 2020
)
2.29
"Phenazopyridine is a urinary analgesic; commonly seen side-effects of this drug include, orange discoloration of urine, methemoglobinemia, yellowish skin discoloration, hepatitis and acute renal failure. "( Phenazopyridine associated acute interstitial nephritis and review of literature.
Malik, B; Shailesh, F; Sharma, SG; Singh, M; Tiwari, U, 2014
)
3.29
"Phenazopyridine hydrochloride is a strong analgesic used in the treatment of urinary tract infections."( Determination of phenazopyridine in human plasma via LC-MS and subsequent development of a pharmacokinetic model.
Liu, G; Lu, J; Shang, E; Wei, W; Xiang, B; Xie, S, 2005
)
1.39
"Phenazopyridine (Pyridium) is a commonly used urinary tract analgesic. "( Acute renal failure due to phenazopyridine (Pyridium) overdose: case report and review of the literature.
Abitbol, C; Berho, ME; Chandar, J; Espinoza, V; Onder, AM; Zilleruelo, G, 2006
)
2.07
"Phenazopyridine HCl is a bladder analgesic."( Use of phenazopyridine for reducing discomfort during embryo transfer.
Allsworth, JE; Frishman, GN; Gannon, JB; Wright, KP, 2007
)
1.52
"Phenazopyridine hydrochloride is a strong analgesic used in the treatment of urinary tract infections. "( Development and validation of a gas chromatography-mass spectrometry method for the determination of phenazopyridine in rat plasma: application to the pharmacokinetic study.
Chen, Q; Li, K; Li, P; Li, Q; Liu, J; Zhang, Z, 2007
)
2
"Phenazopyridine hydrochloride is an effective oral urinary analgesic commonly used for the treatment of irritative lower urinary tract conditions. "( Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones.
Crawford, ED; Mulvaney, WP, 1978
)
1.95
"Phenazopyridine is a commonly used urinary tract analgesic. "( Methemoglobinemia and hemolytic anemia after phenazopyridine hydrochloride (Pyridium) administration in end-stage renal disease.
Campbell, HT; Fincher, ME, 1989
)
1.98

Effects

Phenazopyridine has a pronounced analgesic effect and is proved to be an effective and safe drug in patients with acute uncomplicated cystitis. It has been used as a model soil contaminant.

ExcerptReferenceRelevance
"Phenazopyridine has a pronounced analgesic effect and is proved to be an effective and safe drug in patients with acute uncomplicated cystitis."( [Phenazopyridine and fosfomycin for the acute cystitis treatment: results of multicenter randomized study].
Bunova, NE; Davidov, MI; Lunev, AA; Meltsina, MN; Metelkin, AM; O, PR, 2021
)
2.97
"Phenazopyridine has been known for a long time."( [Influence of phenazopyridine on the well-being of patients during and after cystoscopy].
Makushin, DG; Mirzakadiev, AA; Tsukanov, AY; Zolotov, IA, 2020
)
1.64
"Phenazopyridine has a pronounced analgesic effect and is proved to be an effective and safe drug in patients with acute uncomplicated cystitis."( [Phenazopyridine and fosfomycin for the acute cystitis treatment: results of multicenter randomized study].
Bunova, NE; Davidov, MI; Lunev, AA; Meltsina, MN; Metelkin, AM; O, PR, 2021
)
2.97
"Phenazopyridine has been used as a model soil contaminant."( Photocatalytic degradation of phenazopyridine contaminant in soil with direct solar light.
Ateeq, M; Helal, MH; Hilal, HS; Zyoud, A; Zyoud, SH, 2019
)
1.52
"Phenazopyridine has been associated with methemoglobinemia in patients who have received an overdose, have decreased renal function, or are discovered to be unusually susceptible to the drug (ie, they may have an undetected NADH methemoglobin reductase deficiency). "( Acquired methemoglobinemia from multiple oxidants.
Bailey, MK; Baker, JD; Conroy, JM; Dorman, BH; Martin, WJ, 1993
)
1.73

Toxicity

There was no difference in adverse drug reactions among patients receiving phenazopyridine for >14 days compared to a matched comparator group.

ExcerptReferenceRelevance
" The effect of these drugs was also examined in mice challenged with toxic doses of acetaminophen."( Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice.
Battaglia, G; Freitas, I; Griffini, P; Ngomba, RT; Nicoletti, F; Richelmi, P; Storto, M; Vairetti, M, 2003
)
0.32
") substantially reduced liver necrosis and the production of ROS, although it did not affect the conversion of acetaminophen into the toxic metabolite, N-acetylbenzoquinoneimine."( Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice.
Battaglia, G; Freitas, I; Griffini, P; Ngomba, RT; Nicoletti, F; Richelmi, P; Storto, M; Vairetti, M, 2003
)
0.32
" Pyridium toxicity has been previously reported, however, most cases result in a single adverse effect."( Multiple adverse effects of pyridium: a case report.
Dewar, JC; Haigh, C, 2006
)
0.33
" The objective of this study was to compare the incidence of adverse drug reactions in patients with radiation cystitis receiving long-term phenazopyridine (>14-day supply) compared to a matched comparator group."( Safety analysis of long-term phenazopyridine use for radiation cystitis.
Britnell, SR; Brown, JN; Shore, SN, 2020
)
1.05
"This retrospective cohort study compared adverse events among cancer patients with and without phenazopyridine exposure."( Safety analysis of long-term phenazopyridine use for radiation cystitis.
Britnell, SR; Brown, JN; Shore, SN, 2020
)
1.07
"There was no difference in adverse drug reactions among patients receiving phenazopyridine for >14 days compared to a matched comparator group."( Safety analysis of long-term phenazopyridine use for radiation cystitis.
Britnell, SR; Brown, JN; Shore, SN, 2020
)
1.08
" The tolerance of therapy was evaluated by the presence of adverse events."( [Efficiency and safety of phenazopyridine for treatment of uncomplicated urinary tract infection: results of multi-center, randomized, placebo-controlled, clinical study].
Chibirov, KH; Kagan, OF; Petrov, SB; Slesarevskaya, MN; Topuzov, ME; Voronova, EN, 2020
)
0.86
" There were no serious adverse events while taking phenazopyridine."( [Efficiency and safety of phenazopyridine for treatment of uncomplicated urinary tract infection: results of multi-center, randomized, placebo-controlled, clinical study].
Chibirov, KH; Kagan, OF; Petrov, SB; Slesarevskaya, MN; Topuzov, ME; Voronova, EN, 2020
)
1.11

Pharmacokinetics

This paper describes a new LC-MS method for the determination of phenazopyridine. It also describes the subsequent development of a pharmacokinetic model for phenazobyridine in vivo.

ExcerptReferenceRelevance
"This paper describes a new LC-MS method for the determination of phenazopyridine and the subsequent development of a pharmacokinetic model for phenazopyridine in vivo."( Determination of phenazopyridine in human plasma via LC-MS and subsequent development of a pharmacokinetic model.
Liu, G; Lu, J; Shang, E; Wei, W; Xiang, B; Xie, S, 2005
)
0.91
" DRUG-KNT--a pharmacokinetic software developed previously for fitting one and two compartment kinetics using the iterative curve stripping method--was modified and a revised subroutine was incorporated to solve double-peak models."( A simple pharmacokinetics subroutine for modeling double peak phenomenon.
Mahmoudian, M; Mirfazaelian, A, 2006
)
0.33
" Thus, the present study was designed to compare the pharmacokinetic behaviour of ciprofloxacin administered alone versus ciprofloxacin combined with phenazopyridine."( Ciprofloxacin bioavailability is enhanced by oral co-administration with phenazopyridine: a pharmacokinetic study in a Mexican population.
Angeles, AP; Fernández S, A; Marcelín-Jiménez, G; Martínez-Rossier, L, 2006
)
0.76
" The area under the concentration-time curve to last measurable concentration (AUC(t)), area under the concentration-time curve extrapolated to infinity (AUC(infinity)), peak plasma concentration (C(max)), time to reach C(max) (t(max)), mean residence time (MRT), elimination constant (k(e)) and elimination half-life (t(1/2)) were determined from plasma concentrations of both treatments and considered as primary variables for statistical analysis."( Ciprofloxacin bioavailability is enhanced by oral co-administration with phenazopyridine: a pharmacokinetic study in a Mexican population.
Angeles, AP; Fernández S, A; Marcelín-Jiménez, G; Martínez-Rossier, L, 2006
)
0.57
" The main pharmacokinetic parameters obtained were T(max) = (0."( Development and validation of a gas chromatography-mass spectrometry method for the determination of phenazopyridine in rat plasma: application to the pharmacokinetic study.
Chen, Q; Li, K; Li, P; Li, Q; Liu, J; Zhang, Z, 2007
)
0.56

Bioavailability

Oral co-administration of phenazopyridine increases ciprofloxacin bioavailability with regard to the amount absorbed (AUC) and permanence in the body (MRT) The aim of this study is to develop a nano-sized cocrystal of PAP with phthalimide.

ExcerptReferenceRelevance
" On the other hand, the bioavailability of PNHCl in humans was the same when lactose was used with either gelatin, syrup or methylcellulose, but higher than that obtained with a combination of calcium carbonate and Eudragit E 15%."( Effect of some additives on the properties of phenazopyridine hydrochloride granules and their corresponding tablets.
Abdel-Aleem, H; el-Sabbagh, HM; Ghanem, A; Meshali, M, 1984
)
0.53
" Bioavailability studies proved that bentonite decreased the rate as well as extent of absorption of PN ."( Adsorption of phenazopyridine hydrochloride on pharmaceutical adjuvants.
Meshali, MM, 1982
)
0.62
"Oral co-administration of phenazopyridine increases ciprofloxacin bioavailability with regard to the amount absorbed (AUC) and permanence in the body (MRT), which could be useful during treatment."( Ciprofloxacin bioavailability is enhanced by oral co-administration with phenazopyridine: a pharmacokinetic study in a Mexican population.
Angeles, AP; Fernández S, A; Marcelín-Jiménez, G; Martínez-Rossier, L, 2006
)
0.87
" The aim of this study is to develop a nano-sized cocrystal of phenazopyridine (PAP) with phthalimide (PI) to enhance the release rate and oral bioavailability of PAP."( Phenazopyridine-phthalimide nano-cocrystal: Release rate and oral bioavailability enhancement.
Chen, JM; Huang, Y; Lai, ZH; Li, JM; Lu, TB; Wu, J, 2017
)
2.14

Dosage Studied

The suggested method is highly specific and can be used to determine phenazopyridine HCl in the presence of most drugs commonly found in pharmaceutical dosage forms or administered therapeutically. Such products should be avoided in cats unless a safe, effective dosage for phenazopsyridine is established.

ExcerptRelevanceReference
" Such products should be avoided in cats unless a safe, effective dosage for phenazopyridine can be established."( Phenazopyridine toxicosis in the cat.
Harvey, JW; Kornick, HP, 1976
)
1.93
" The suggested method is highly specific and can be used to determine phenazopyridine HCl in the presence of most drugs commonly found in pharmaceutical dosage forms or administered therapeutically."( Amperometric determination of phenazopyridine hydrochloride in a flowing stream at the glassy carbon electrode.
Belal, F,
)
0.65
" SIB-1757 produced a partial reversal of tactile allodynia with a shallow dose-response curve ranging over three-orders of magnitude; SIB-1757 was inactive against allodynia when given systemically."( Peripheral and spinal antihyperalgesic activity of SIB-1757, a metabotropic glutamate receptor (mGLUR(5)) antagonist, in experimental neuropathic pain in rats.
Dogrul, A; Lai, J; Malan, TP; Ossipov, MH; Porreca, F, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
local anaestheticAny member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
anticoronaviral agentAny antiviral agent which inhibits the activity of coronaviruses.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
benzochromene
diaminopyridineCompounds containing a pyridine skeleton substituted by two amino groups.
monoazo compoundCompounds containing single -N=N- group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (36)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency11.22020.004023.8416100.0000AID485290
Chain A, Ferritin light chainEquus caballus (horse)Potency11.22025.623417.292931.6228AID485281
LuciferasePhotinus pyralis (common eastern firefly)Potency11.38540.007215.758889.3584AID411; AID624030
USP1 protein, partialHomo sapiens (human)Potency35.17970.031637.5844354.8130AID504865
GLS proteinHomo sapiens (human)Potency17.78280.35487.935539.8107AID624170
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency0.63100.00137.762544.6684AID914; AID915
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency11.22020.035520.977089.1251AID504332
hemoglobin subunit betaHomo sapiens (human)Potency12.58930.31629.086131.6228AID925
cytochrome P450 2C19 precursorHomo sapiens (human)Potency7.94330.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency15.84890.00636.904339.8107AID883
mitogen-activated protein kinase 1Homo sapiens (human)Potency15.84890.039816.784239.8107AID995
ubiquitin carboxyl-terminal hydrolase 2 isoform aHomo sapiens (human)Potency3.98110.65619.452025.1189AID927
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency0.63100.00798.23321,122.0200AID2546
gemininHomo sapiens (human)Potency29.85540.004611.374133.4983AID624296
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency14.38180.005612.367736.1254AID624032
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
lamin isoform A-delta10Homo sapiens (human)Potency1.00000.891312.067628.1838AID1487
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency15.84890.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Disintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)Potency3.98111.584913.004325.1189AID927
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)28.00000.00022.45859.9600AID1804171
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of epidermal growth factor receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to hypoxiaDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
neutrophil mediated immunityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
germinal center formationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of leukocyte chemotaxisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
proteolysisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membrane protein ectodomain proteolysisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell adhesionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch receptor processingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell population proliferationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to xenobiotic stimulusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of T cell chemotaxisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
protein processingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
signal releaseDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
B cell differentiationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell growthDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cell migrationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
response to lipopolysaccharideDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of chemokine productionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of tumor necrosis factor productionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
regulation of mast cell apoptotic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
T cell differentiation in thymusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell adhesion mediated by integrinDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
wound healing, spreading of epidermal cellsDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
amyloid precursor protein catabolic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of blood vessel endothelial cell migrationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of cyclin-dependent protein serine/threonine kinase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of epidermal growth factor-activated receptor activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
spleen developmentDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell motilityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
defense response to Gram-positive bacteriumDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cellular response to high density lipoprotein particle stimulusDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
commissural neuron axon guidanceDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
negative regulation of cold-induced thermogenesisDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycleDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of tumor necrosis factor-mediated signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
positive regulation of vascular endothelial cell proliferationDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch signaling pathwayDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
endopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metalloendopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Notch bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
interleukin-6 receptor bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
integrin bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
protein bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
peptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metallopeptidase activityDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
SH3 domain bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytokine bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
PDZ domain bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
tumor necrosis factor bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metal ion bindingDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
metalloendopeptidase activity involved in amyloid precursor protein catabolic processDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
cell-cell junctionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
focal adhesionDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
ruffle membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
Golgi membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytoplasmDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
endoplasmic reticulum lumenDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cytosolDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
cell surfaceDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
actin cytoskeletonDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
apical plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
membrane raftDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
plasma membraneDisintegrin and metalloproteinase domain-containing protein 17Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID361173Cytotoxicity against human HL60 cells after 3 days by MTT assay2001Journal of natural products, Jun, Volume: 64, Issue:6
Chemical constituents from Lippia sidoides and cytotoxic activity.
AID361175Cytotoxicity against human CEM cells after 3 days by MTT assay2001Journal of natural products, Jun, Volume: 64, Issue:6
Chemical constituents from Lippia sidoides and cytotoxic activity.
AID361174Cytotoxicity against human SW1573 cells after 3 days by MTT assay2001Journal of natural products, Jun, Volume: 64, Issue:6
Chemical constituents from Lippia sidoides and cytotoxic activity.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1804171DRC analysis by immunofluorescence from Article 10.1128/AAC.00819-20: \\Identification of Antiviral Drug Candidates against SARS-CoV-2 from FDA-Approved Drugs.\\2020Antimicrobial agents and chemotherapy, 06-23, Volume: 64, Issue:7
Identification of Antiviral Drug Candidates against SARS-CoV-2 from FDA-Approved Drugs.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID106806Inhibition of malate dehydrogenase (MDH) at 400 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1717771Selectivity ratio of CC50 for Rhesus macaque LLC-MK2 cells to EC50 for HCoV-NL63 infected in Rhesus macaque LLC-MK2 cells2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID52790Inhibition of chymotrypsin at 250 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID43581Inhibition of beta-lactamase at 100 uM2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID127482Ability to bind to monoclonal antibody IgE (Lb4), expressed as association constant (LogKA)1996Journal of medicinal chemistry, Sep-27, Volume: 39, Issue:20
Comparative molecular field analysis of haptens docked to the multispecific antibody IgE(Lb4)
AID1717752cytotoxicity against golden hamster BHK-21 cells incubated for 72 hrs by MTT assay2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1717770Cytotoxicity against Rhesus macaque LLC-MK2 cells incubated for 72 hrs by MTT assay2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID515780Intrinsic solubility of the compound in water2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
QSAR-based solubility model for drug-like compounds.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1717753Selectivity index, ratio of CC50 for golden hamster BHK-21 cells to EC50 for wild type HCoV-OC43 infected in BHK-21 cells2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID384955Intrinsic aqueous solubility at pH 10 by shake-flask method2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Molecular characteristics for solid-state limited solubility.
AID1717769Antiviral activity against HCoV-NL63 infected in Rhesus macaque LLC-MK2 cells incubated for 72 hrs by RT-PCR method2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1053268Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Experimental confirmation of new drug-target interactions predicted by Drug Profile Matching.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1717751Antiviral activity against wild type HCoV-OC43 infected in BHK-21 cells incubated for 72 hrs by RT-PCR method2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2).
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1053269Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Experimental confirmation of new drug-target interactions predicted by Drug Profile Matching.
AID237685Lipophilicity determined as logarithm of the partition coefficient in the alkane/water system2005Journal of medicinal chemistry, May-05, Volume: 48, Issue:9
Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).
AID1745854NCATS anti-infectives library activity on HEK293 viability as a counter-qHTS vs the C. elegans viability qHTS2023Disease models & mechanisms, 03-01, Volume: 16, Issue:3
In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1745855NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay2023Disease models & mechanisms, 03-01, Volume: 16, Issue:3
In vivo quantitative high-throughput screening for drug discovery and comparative toxicology.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (272)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990110 (40.44)18.7374
1990's24 (8.82)18.2507
2000's51 (18.75)29.6817
2010's59 (21.69)24.3611
2020's28 (10.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 104.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index104.51 (24.57)
Research Supply Index5.73 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index232.14 (26.88)
Search Engine Supply Index2.44 (0.95)

This Compound (104.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials24 (8.51%)5.53%
Reviews0 (0.00%)6.00%
Reviews14 (4.96%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies79 (28.01%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other165 (58.51%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]