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Identification
NameHistamine
Accession NumberDB05381  (APRD01015, DB05891, DB11320, DB00667)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA depressor amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.
Structure
Thumb
Synonyms
1H-Imidazole-4-ethanamine
2-(4-imidazolyl)ethylamine
4-imidazoleethylamine
5-imidazoleethylamine
beta-aminoethylglyoxaline
beta-aminoethylimidazole
External IDs NSC-33792
Product Ingredients
IngredientUNIICASInChI KeyDetails
Histamine dihydrochloride3POA0Q644U 56-92-8PPZMYIBUHIPZOS-UHFFFAOYSA-NDetails
Histamine phosphateQWB37T4WZZ 51-74-1ZHIBQGJKHVBLJJ-UHFFFAOYSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CepleneInjection, solution0.5 mg/0.5mlSubcutaneousMeda Ab2008-10-07Not applicableEu
Histamine Phosphate Injection USP Liq ScLiquid1 mgSubcutaneousBioniche Pharma (Canada) Ltd1994-12-312014-11-24Canada
Histamine Phosphate Injection USP, 1mg/mlLiquid1 mgSubcutaneousAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Histamine Positive Skin Test ControlSolution2.75 mg/mLPercutaneousAlk Abello, Inc.1989-10-23Not applicableUs
Histamine Positive Skin Test ControlInjection, solution.275 mg/mLIntradermalAlk Abello, Inc.1989-10-23Not applicableUs
HistatrolSolution2.75 mgPercutaneousAlk Abello, Inc.1984-12-31Not applicableCanada
HistatrolSolution0.275 mgIntradermalAlk Abello, Inc.1984-12-31Not applicableCanada
Positive Skin Test Control - HistamineInjection6 mg/mLPercutaneousJubilant Hollisterstier Llc1995-06-15Not applicableUs
Positive Skin Test Control-histamineLiquid6 mgPercutaneousJubilant Hollisterstier LlcNot applicableNot applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Australian Dream Back PainCream.05 g/100gTopicalNature's Health Connection2014-07-10Not applicableUs
Australian Dream Carpal Tunnel PainCream.025 g/100gTopicalNature's Health Connection2016-12-09Not applicableUs
Australian Dream Pain Relieving ArthritisCream.025 g/100gTopicalNature's Health Connection2011-02-09Not applicableUs
Cvs Arthritis Pain ReliefCream.025 g/100gTopicalCvs Health2016-05-30Not applicableUs
Dr. Freds Miracle RubCream.25 mg/mLTopicalPure Source, Llc2013-06-06Not applicableUs
Glucosamine Cream Extra StrengthCream.05 g/100gTopicalQ.A. Laboratories2017-04-01Not applicableUs
Mancore Muscle Mend Roll-ON Pain RelieverLotion.6 mg/mLTopicalR2 Distribution, LLC2014-08-27Not applicableUs
Pain Relieving ArthritisCream.025 g/100gTopicalVelocity Pharma Llc2017-03-01Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
CepleneNot Available
Brand mixtures
NameLabellerIngredients
Abee MedCrossover Telecom Llc
Activon Ultra Strength ArthritisFamily First Pharmaceuticals, Inc.
Alo Therapeutic MassageCmi Therapy Solutions
Alo Therapeutic Massage Pain RelievingTheraplex Solutions
Arthritis ReliefPure Source, Llc
Arthrocare LotionAvacare, Division Of Jeunique International Inc.
Camphomex1st Class Pharmaceuticals
Painmd MaxOmg Medical Group, Llc
Ponos Natural Pain ReliefDr. Mike's Vitamins, Llc
RematexHome Aide Diganostics, Inc.
SimanixHome Aide Diganostics, Inc.
Categories
UNII820484N8I3
CAS number51-45-6
WeightAverage: 111.1451
Monoisotopic: 111.079647303
Chemical FormulaC5H9N3
InChI KeyNTYJJOPFIAHURM-UHFFFAOYSA-N
InChI
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
IUPAC Name
2-(1H-imidazol-4-yl)ethan-1-amine
SMILES
NCCC1=CNC=N1
Pharmacology
IndicationHistamine phosphate is indicated as a diagnostic aid for evaluation of gastric acid secretory function.
Structured Indications Not Available
PharmacodynamicsHistamine stimulates gastric gland secretion, causing an increased secretion of gastric juice of high acidity. This action is probably due mainly to a direct action on parietal and chief gland cells.
Mechanism of actionHistamine acts directly on the blood vessels to dilate arteries and capillaries; this action is mediated by both H 1- and H 2-receptors. Capillary dilatation may produce flushing of the face, a decrease in systemic blood pressure, and gastric gland secretion, causing an increased secretion of gastric juice of high acidity. Increased capillary permeability accompanies capillary dilatation, producing an outward passage of plasma protein and fluid into the extracellular spaces, an increase in lymph flow and protein content, and the formation of edema. In addition, histamine has a direct stimulant action on smooth muscle, producing contraction if H 1-receptors are activated, or mostly relaxation if H 2-receptors are activated. Also in humans, the stimulant effect of histamine may cause contraction of the intestinal muscle. However, little effect is noticed on the uterus, bladder, or gallbladder. Histamine has some stimulant effect on duodenal, salivary, pancreatic, bronchial, and lacrimal glands. Histamine also can bind to H3 and H4 receptors which are involved in the CNS/PNS neurotransmitter release and immune system chemotaxis, respectively.
TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
agonist
HumanP35367 details
Histamine H2 receptorProteinyes
agonist
HumanP25021 details
Histamine H3 receptorProteinyes
agonist
HumanQ9Y5N1 details
Histamine H4 receptorProteinunknown
agonist
HumanQ9H3N8 details
Related Articles
AbsorptionReadily absorbed after parenteral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic. Histamine is rapidly metabolized by methylation and oxidation. Methylation involves ring methylation and catalyzation by the enzyme histamine-N-methyltransferase, producing N-methylhistamine, which is mostly converted to N-methyl imidazole acetic acid. 2 to 3% excreted as free histamine, 4 to 8% as N-methylhistamine, 42 to 47% as N-methyl imidazole acetic acid, 9 to 11% as imidazole acetic acid, and 16 to 23% as imidazole acetic acid riboside.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=807 mg/kg (mouse, oral). Side effects can lead to hypertension, hypotension, headache, dizziness, nervousness and tachycardia. Large overdoses can lead to seizures.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Histamine Phosphate can be decreased when combined with Abiraterone.Approved
AmiodaroneThe metabolism of Histamine Phosphate can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Histamine Phosphate can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Histamine Phosphate can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Histamine Phosphate can be decreased when combined with Atomoxetine.Approved
BexaroteneThe serum concentration of Histamine Phosphate can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Histamine Phosphate can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Histamine Phosphate can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Histamine Phosphate can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe serum concentration of Histamine Phosphate can be increased when it is combined with Bupropion.Approved
CapecitabineThe metabolism of Histamine Phosphate can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Histamine Phosphate can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Histamine Phosphate can be increased when it is combined with Ceritinib.Approved
CholecalciferolThe metabolism of Histamine Phosphate can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ClarithromycinThe metabolism of Histamine Phosphate can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Histamine Phosphate can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Histamine Phosphate can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Histamine Phosphate can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Histamine Phosphate can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Histamine Phosphate can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Histamine Phosphate can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Histamine Phosphate can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Histamine Phosphate can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Histamine Phosphate can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Histamine Phosphate can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Histamine Phosphate can be decreased when combined with Delavirdine.Approved
DexamethasoneThe serum concentration of Histamine Phosphate can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe metabolism of Histamine Phosphate can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Histamine Phosphate can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Histamine Phosphate can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Histamine Phosphate can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Histamine Phosphate can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Histamine Phosphate can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Histamine Phosphate can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Histamine Phosphate can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtravirineThe serum concentration of Histamine Phosphate can be decreased when it is combined with Etravirine.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Histamine Phosphate.Approved
FloxuridineThe metabolism of Histamine Phosphate can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Histamine Phosphate can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Histamine Phosphate can be decreased when combined with Fluorouracil.Approved
FluvastatinThe metabolism of Histamine Phosphate can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Histamine Phosphate can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Histamine Phosphate can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Histamine Phosphate can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Histamine Phosphate can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Histamine Phosphate can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Histamine Phosphate can be decreased when combined with Gemfibrozil.Approved
IdelalisibThe serum concentration of Histamine Phosphate can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Histamine Phosphate can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Histamine Phosphate can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Histamine Phosphate can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Histamine Phosphate can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Histamine Phosphate can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Histamine Phosphate can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Histamine Phosphate can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Histamine Phosphate can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe metabolism of Histamine Phosphate can be decreased when combined with Leflunomide.Approved, Investigational
LopinavirThe metabolism of Histamine Phosphate can be decreased when combined with Lopinavir.Approved
LosartanThe metabolism of Histamine Phosphate can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Histamine Phosphate can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Histamine Phosphate can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Histamine Phosphate can be decreased when it is combined with Lumacaftor.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Histamine Phosphate.Approved, Investigational
MifepristoneThe serum concentration of Histamine Phosphate can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Histamine Phosphate can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Histamine Phosphate can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Histamine Phosphate can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Histamine Phosphate can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Histamine Phosphate can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Histamine Phosphate can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Histamine Phosphate can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Histamine Phosphate can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Histamine Phosphate can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Histamine Phosphate can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Histamine Phosphate can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Histamine Phosphate can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Histamine Phosphate can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Histamine Phosphate can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Histamine Phosphate can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Histamine Phosphate can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Histamine Phosphate can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Histamine Phosphate can be increased when combined with Primidone.Approved, Vet Approved
PyrimethamineThe metabolism of Histamine Phosphate can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinineThe metabolism of Histamine Phosphate can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Histamine Phosphate can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Histamine Phosphate can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Histamine Phosphate can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Histamine Phosphate can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Histamine Phosphate can be decreased when combined with Ritonavir.Approved, Investigational
SaquinavirThe metabolism of Histamine Phosphate can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Histamine Phosphate can be increased when combined with Secobarbital.Approved, Vet Approved
SildenafilThe metabolism of Histamine Phosphate can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Histamine Phosphate can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Histamine Phosphate can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Histamine Phosphate can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Histamine Phosphate can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Histamine Phosphate can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Histamine Phosphate can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Histamine Phosphate can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Histamine Phosphate can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Histamine Phosphate can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Histamine Phosphate can be decreased when combined with Telithromycin.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Histamine Phosphate.Approved
TicagrelorThe metabolism of Histamine Phosphate can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Histamine Phosphate can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Histamine Phosphate can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Histamine Phosphate can be decreased when combined with Tolbutamide.Approved
TrimethoprimThe metabolism of Histamine Phosphate can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Histamine Phosphate can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Histamine Phosphate can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Histamine Phosphate can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Histamine Phosphate can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Histamine Phosphate can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Histamine Phosphate can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Histamine Phosphate can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Middleton M, Sarno M, Agarwala SS, Glaspy J, Laurent A, McMasters K, Naredi P, O'Day S, Whitman E, Danson S, Cosford R, Gehlsen K: Pharmacokinetics of histamine dihydrochloride in healthy volunteers and cancer patients: implications for combined immunotherapy with interleukin-2. J Clin Pharmacol. 2002 Jul;42(7):774-81. [PubMed:12092744 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 36:36.00
  • 36:89.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedScreeningAllergic Rhinitis (AR)1
1, 2WithdrawnTreatmentMyelodysplastic Syndromes1
2CompletedScreeningAllergic Skin Reaction1
2CompletedTreatmentRhinitis, Allergic, Seasonal1
2Unknown StatusPreventionProphylaxis of migraine headaches1
2Unknown StatusTreatmentKidney Cancer1
3CompletedTreatmentLeukemias1
3CompletedTreatmentOsteoarthritis of the Knees1
3Unknown StatusTreatmentMelanoma (Skin) / Metastatic Cancers1
4CompletedTreatmentAcute Myeloid Leukaemias (AML)1
Not AvailableCompletedDiagnosticAllergic Rhinitis (AR) / Asthma1
Not AvailableRecruitingBasic ScienceMiddle Ear Disease / Nasal Allergies1
Not AvailableRecruitingBasic ScienceNormal Skin / Photoaged Skin1
Not AvailableTerminatedBasic ScienceHouse Dust Mite Allergy1
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
Packagers
Dosage forms
FormRouteStrength
StickTopical
LiquidTopical
CreamTopical.05 g/100g
SprayTopical
Injection, solutionSubcutaneous0.5 mg/0.5ml
CreamTopical.025 g/100g
CreamTopical.25 mg/mL
LiquidSubcutaneous1 mg
Injection, solutionIntradermal.275 mg/mL
SolutionPercutaneous2.75 mg/mL
SolutionIntradermal0.275 mg
SolutionPercutaneous2.75 mg
LotionTopical.6 mg/mL
CreamTopical
InjectionPercutaneous6 mg/mL
LiquidPercutaneous6 mg
Prices
Unit descriptionCostUnit
Histamine phosphate 100% cryst14.38USD g
Histatrol 1:10000 vial13.18USD ml
Histamine di-hcl powder12.6USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point139 °C (phosphate salt)Not Available
Predicted Properties
PropertyValueSource
Water Solubility169.0 mg/mLALOGPS
logP-0.69ALOGPS
logP-0.7ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)14.46ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.66 m3·mol-1ChemAxon
Polarizability12.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9931
Blood Brain Barrier+0.8784
Caco-2 permeable-0.5409
P-glycoprotein substrateNon-substrate0.6136
P-glycoprotein inhibitor INon-inhibitor0.9639
P-glycoprotein inhibitor IINon-inhibitor0.9013
Renal organic cation transporterNon-inhibitor0.529
CYP450 2C9 substrateNon-substrate0.8735
CYP450 2D6 substrateNon-substrate0.7217
CYP450 3A4 substrateNon-substrate0.7528
CYP450 1A2 substrateNon-inhibitor0.8045
CYP450 2C9 inhibitorNon-inhibitor0.8396
CYP450 2D6 inhibitorNon-inhibitor0.8574
CYP450 2C19 inhibitorNon-inhibitor0.9187
CYP450 3A4 inhibitorNon-inhibitor0.7351
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8404
Ames testNon AMES toxic0.7103
CarcinogenicityNon-carcinogens0.8747
BiodegradationNot ready biodegradable0.9377
Rat acute toxicity2.4808 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9413
hERG inhibition (predictor II)Non-inhibitor0.8061
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0f79-5910000000-9946e1707fcaf5562f88View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-2910000000-8c243055df15d6ce8116View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9710000000-bf79b524c104e1cc94baView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-2900000000-a40a3d0aed04ccfe9365View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00dr-3910000000-44d8fb649d4e75eba66cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ot-9600000000-06c58d75770dfd76aeabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-0135b8f0628e592abc22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-6fccc177582b320a48aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-1900000000-6cda8885da689473fb42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-9100000000-37450d9969c24ad44ad7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9000000000-e9e368926d3146437e13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-015a-9000000000-f51ad8a8259595600938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00lu-9000000000-3e02d5b58a7c9f77ec53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-046407320168835599f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-b06ddb1eb7ed3ddf4f69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-a93565f24c40eddb6cf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-71d70766bb4f9d3b13a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-2705dc2d177edbc4faa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6900000000-9e9ebaae6f68b4c2d89dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9d4fe74f18b21423615dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-9d57c893be8c75ce8178View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Miyoshi K, Das AK, Fujimoto K, Horio S, Fukui H: Recent advances in molecular pharmacology of the histamine systems: regulation of histamine H1 receptor signaling by changing its expression level. J Pharmacol Sci. 2006 May;101(1):3-6. Epub 2006 Apr 28. [PubMed:16648669 ]
  2. Han SK, Mancino V, Simon MI: Phospholipase Cbeta 3 mediates the scratching response activated by the histamine H1 receptor on C-fiber nociceptive neurons. Neuron. 2006 Nov 22;52(4):691-703. [PubMed:17114052 ]
  3. Spahr L, Coeytaux A, Giostra E, Hadengue A, Annoni JM: Histamine H1 blocker hydroxyzine improves sleep in patients with cirrhosis and minimal hepatic encephalopathy: a randomized controlled pilot trial. Am J Gastroenterol. 2007 Apr;102(4):744-53. Epub 2007 Jan 11. [PubMed:17222324 ]
  4. Suzuki K, Morokata T, Morihira K, Sato I, Takizawa S, Kaneko M, Takahashi K, Shimizu Y: A dual antagonist for chemokine CCR3 receptor and histamine H1 receptor. Eur J Pharmacol. 2007 Jun 1;563(1-3):224-32. Epub 2007 Feb 8. [PubMed:17336292 ]
  5. Tanimoto A, Wang KY, Murata Y, Kimura S, Nomaguchi M, Nakata S, Tsutsui M, Sasaguri Y: Histamine upregulates the expression of inducible nitric oxide synthase in human intimal smooth muscle cells via histamine H1 receptor and NF-kappaB signaling pathway. Arterioscler Thromb Vasc Biol. 2007 Jul;27(7):1556-61. Epub 2007 May 3. [PubMed:17478759 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Histamine receptor activity
Specific Function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) si...
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular Weight:
40097.65 Da
References
  1. Francis H, Franchitto A, Ueno Y, Glaser S, DeMorrow S, Venter J, Gaudio E, Alvaro D, Fava G, Marzioni M, Vaculin B, Alpini G: H3 histamine receptor agonist inhibits biliary growth of BDL rats by downregulation of the cAMP-dependent PKA/ERK1/2/ELK-1 pathway. Lab Invest. 2007 May;87(5):473-87. Epub 2007 Mar 5. [PubMed:17334413 ]
  2. Soga F, Katoh N, Kishimoto S: Histamine prevents apoptosis in human monocytes. Clin Exp Allergy. 2007 Mar;37(3):323-30. [PubMed:17359382 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Histamine receptor activity
Specific Function:
The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive activity (spontaneous activity in the absence of agonist). Agonist stimulation of isoform 3 neither modified adenylate cyclase activity nor induced intracellular calcium mobilization.
Gene Name:
HRH3
Uniprot ID:
Q9Y5N1
Molecular Weight:
48670.81 Da
References
  1. Petroianu G, Arafat K, Sasse BC, Stark H: Multiple enzyme inhibitions by histamine H3 receptor antagonists as potential procognitive agents. Pharmazie. 2006 Mar;61(3):179-82. [PubMed:16599255 ]
  2. Garduno-Torres B, Arias-Montano JA: Homologous down-regulation of histamine H3 receptors in rat striatal slices. Synapse. 2006 Aug;60(2):165-71. [PubMed:16715497 ]
  3. Minick DJ, Copley RC, Szewczyk JR, Rutkowske RD, Miller LA: An investigation of the absolute configuration of the potent histamine H3 receptor antagonist GT-2331 using vibrational circular dichroism. Chirality. 2007 Sep;19(9):731-40. [PubMed:17575572 ]
  4. Arrang JM: [The histamine H3 receptor: a new target for the treatment of arousal and cognitive disorders]. Ann Pharm Fr. 2007 Jul;65(4):275-84. [PubMed:17652997 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Histamine receptor activity
Specific Function:
The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist).
Gene Name:
HRH4
Uniprot ID:
Q9H3N8
Molecular Weight:
44495.375 Da
References
  1. Blaya B, Nicolau-Galmes F, Jangi SM, Ortega-Martinez I, Alonso-Tejerina E, Burgos-Bretones J, Perez-Yarza G, Asumendi A, Boyano MD: Histamine and histamine receptor antagonists in cancer biology. Inflamm Allergy Drug Targets. 2010 Jul;9(3):146-57. [PubMed:20632959 ]
  2. Yu B, Shao Y, Li P, Zhang J, Zhong Q, Yang H, Hu X, Chen B, Peng X, Wu Q, Chen Y, Guan M, Wan J, Zhang W: Copy number variations of the human histamine H4 receptor gene are associated with systemic lupus erythematosus. Br J Dermatol. 2010 Nov;163(5):935-40. doi: 10.1111/j.1365-2133.2010.09928.x. [PubMed:20618322 ]
  3. Cowden JM, Riley JP, Ma JY, Thurmond RL, Dunford PJ: Histamine H4 receptor antagonism diminishes existing airway inflammation and dysfunction via modulation of Th2 cytokines. Respir Res. 2010 Jun 24;11:86. doi: 10.1186/1465-9921-11-86. [PubMed:20573261 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Histamine n-methyltransferase activity
Specific Function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular Weight:
33294.765 Da
References
  1. Garcia-Martin E, Ayuso P, Martinez C, Blanca M, Agundez JA: Histamine pharmacogenomics. Pharmacogenomics. 2009 May;10(5):867-83. doi: 10.2217/pgs.09.26. [PubMed:19450133 ]
  2. Okinaga S, Ohrui T, Nakazawa H, Yamauchi K, Sakurai E, Watanabe T, Sekizawa K, Sasaki H: The role of HMT (histamine N-methyltransferase) in airways: a review. Methods Find Exp Clin Pharmacol. 1995 Nov;17 Suppl C:16-20. [PubMed:8750789 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  2. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]
  3. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  4. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576 ]
  5. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
  2. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]
  3. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  4. Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084 ]
  5. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
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Drug created on November 18, 2007 11:24 / Updated on February 01, 2017 08:25