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Identification
NameMecamylamine
Accession NumberDB00657  (APRD00458)
TypeSmall Molecule
GroupsApproved
Description

A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool. [PubChem]

Structure
Thumb
Synonyms
Versamine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mecamylamine Hydrochloridetablet2.5 mg/1oralNexgen Pharma, Inc.2013-03-19Not applicableUs
Vecamyltablet2.5 mg/1oralTuring Pharmaceuticals2013-03-19Not applicableUs
Vecamyltablet2.5 mg/1oralManchester Pharmaceuticals2013-03-19Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
InversineTargacept
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mecamylamine hydrochloride
Thumb
  • InChI Key: PKVZBNCYEICAQP-UHFFFAOYNA-N
  • Monoisotopic Mass: 203.144077416
  • Average Mass: 203.752
DBSALT000652
Categories
UNII6EE945D3OK
CAS number60-40-2
WeightAverage: 167.2911
Monoisotopic: 167.167399677
Chemical FormulaC11H21N
InChI KeyInChIKey=IMYZQPCYWPFTAG-UHFFFAOYSA-N
InChI
InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
IUPAC Name
N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
SMILES
CNC1(C)C2CCC(C2)C1(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Cyclohexylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension
PharmacodynamicsMecamylamine is a potent, oral antihypertensive agent and ganglion blocker, and is a secondary amine. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine crosses the blood-brain and placental barriers.
Mechanism of actionMecamylamine is a ganglionic blocker which prevents stimulation of postsynaptic receptors by acetylcholine released from presynaptic nerve endings. The hypotensive effect of Mecamylamine is attributed to reduction in sympathetic tone, vasodilation, and reduced cardiac output, and is primarily postural.
Related Articles
AbsorptionMecamylamine is almost completely absorbed from the gastrointestinal tract
Volume of distributionNot Available
Protein binding40%
MetabolismNot Available
Route of eliminationMecamylamine is excreted slowly in the urine in the unchanged form. The rate of its renal elimination is influenced markedly by urinary pH. Alkalinization of the urine reduces, and acidification promotes, renal excretion of mecamylamine. Mecamylamine crosses the blood-brain and placental barriers.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9566
Blood Brain Barrier+0.9771
Caco-2 permeable+0.611
P-glycoprotein substrateNon-substrate0.6815
P-glycoprotein inhibitor INon-inhibitor0.8271
P-glycoprotein inhibitor IINon-inhibitor0.889
Renal organic cation transporterNon-inhibitor0.7727
CYP450 2C9 substrateNon-substrate0.7864
CYP450 2D6 substrateNon-substrate0.7207
CYP450 3A4 substrateSubstrate0.5884
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9054
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7435
Ames testNon AMES toxic0.9315
CarcinogenicityNon-carcinogens0.8757
BiodegradationNot ready biodegradable0.6954
Rat acute toxicity2.3843 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9676
hERG inhibition (predictor II)Non-inhibitor0.8756
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Targacept inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral2.5 mg/1
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point249 with decompositionU.S. Patent 2,831,027.
boiling point72 °C at 4.00E+00 mm HgPhysProp
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.124 mg/mLALOGPS
logP3.13ALOGPS
logP2.37ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.83 m3·mol-1ChemAxon
Polarizability20.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,831,027.

General ReferencesNot Available
External Links
ATC CodesC02BB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Mecamylamine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Mecamylamine.
AlfuzosinAlfuzosin may increase the hypotensive activities of Mecamylamine.
AmifostineMecamylamine may increase the hypotensive activities of Amifostine.
AmikacinAmikacin may increase the neuromuscular blocking activities of Mecamylamine.
Ammonium chlorideThe serum concentration of Mecamylamine can be decreased when it is combined with Ammonium chloride.
ArbekacinArbekacin may increase the neuromuscular blocking activities of Mecamylamine.
BrimonidineBrimonidine may increase the antihypertensive activities of Mecamylamine.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Mecamylamine.
ButabarbitalButabarbital may increase the hypotensive activities of Mecamylamine.
ButethalButethal may increase the hypotensive activities of Mecamylamine.
Calcium AcetateThe serum concentration of Mecamylamine can be increased when it is combined with Calcium Acetate.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Mecamylamine.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Mecamylamine.
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Mecamylamine.
ChlorpropamideThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Mecamylamine.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Mecamylamine.
ClindamycinClindamycin may increase the neuromuscular blocking activities of Mecamylamine.
ColistimethateColistimethate may increase the neuromuscular blocking activities of Mecamylamine.
ColistinColistin may increase the neuromuscular blocking activities of Mecamylamine.
DemeclocyclineDemeclocycline may increase the neuromuscular blocking activities of Mecamylamine.
DiazoxideDiazoxide may increase the hypotensive activities of Mecamylamine.
DoxycyclineDoxycycline may increase the neuromuscular blocking activities of Mecamylamine.
DuloxetineMecamylamine may increase the orthostatic hypotensive activities of Duloxetine.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Mecamylamine.
FramycetinFramycetin may increase the neuromuscular blocking activities of Mecamylamine.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Mecamylamine.
GentamicinGentamicin may increase the neuromuscular blocking activities of Mecamylamine.
GliclazideThe risk or severity of adverse effects can be increased when Gliclazide is combined with Mecamylamine.
GlimepirideThe risk or severity of adverse effects can be increased when Glimepiride is combined with Mecamylamine.
GlipizideThe risk or severity of adverse effects can be increased when Glipizide is combined with Mecamylamine.
GlyburideThe risk or severity of adverse effects can be increased when Glyburide is combined with Mecamylamine.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Mecamylamine.
HexamethylenetetramineThe serum concentration of Mecamylamine can be decreased when it is combined with Hexamethylenetetramine.
HexobarbitalHexobarbital may increase the hypotensive activities of Mecamylamine.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Mecamylamine.
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Mecamylamine.
KanamycinKanamycin may increase the neuromuscular blocking activities of Mecamylamine.
Lactic AcidThe serum concentration of Mecamylamine can be increased when it is combined with Sodium lactate.
LevodopaMecamylamine may increase the orthostatic hypotensive activities of Levodopa.
LincomycinLincomycin may increase the neuromuscular blocking activities of Mecamylamine.
MethohexitalMethohexital may increase the hypotensive activities of Mecamylamine.
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Mecamylamine.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Mecamylamine.
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Mecamylamine.
MinocyclineMinocycline may increase the neuromuscular blocking activities of Mecamylamine.
MolsidomineMolsidomine may increase the hypotensive activities of Mecamylamine.
MoxonidineMoxonidine may increase the hypotensive activities of Mecamylamine.
NeomycinNeomycin may increase the neuromuscular blocking activities of Mecamylamine.
NetilmicinNetilmicin may increase the neuromuscular blocking activities of Mecamylamine.
NicorandilNicorandil may increase the hypotensive activities of Mecamylamine.
ObinutuzumabMecamylamine may increase the hypotensive activities of Obinutuzumab.
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Mecamylamine.
PentobarbitalPentobarbital may increase the hypotensive activities of Mecamylamine.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Mecamylamine.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Mecamylamine.
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Mecamylamine.
PrimidonePrimidone may increase the hypotensive activities of Mecamylamine.
QuinineQuinine may increase the hypotensive activities of Mecamylamine.
RibostamycinRibostamycin may increase the neuromuscular blocking activities of Mecamylamine.
RisperidoneMecamylamine may increase the hypotensive activities of Risperidone.
RituximabMecamylamine may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Mecamylamine.
Silver sulfadiazineThe risk or severity of adverse effects can be increased when Silver sulfadiazine is combined with Mecamylamine.
Sodium bicarbonateThe serum concentration of Mecamylamine can be increased when it is combined with Sodium bicarbonate.
SpectinomycinSpectinomycin may increase the neuromuscular blocking activities of Mecamylamine.
StreptomycinStreptomycin may increase the neuromuscular blocking activities of Mecamylamine.
SulfacetamideThe risk or severity of adverse effects can be increased when Sulfacetamide is combined with Mecamylamine.
SulfacytineThe risk or severity of adverse effects can be increased when Sulfacytine is combined with Mecamylamine.
SulfadiazineThe risk or severity of adverse effects can be increased when Sulfadiazine is combined with Mecamylamine.
SulfamerazineThe risk or severity of adverse effects can be increased when Sulfamerazine is combined with Mecamylamine.
SulfamethazineThe risk or severity of adverse effects can be increased when Sulfamethazine is combined with Mecamylamine.
SulfamethoxazoleThe risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Mecamylamine.
SulfanilamideThe risk or severity of adverse effects can be increased when Sulfanilamide is combined with Mecamylamine.
SulfaphenazoleThe risk or severity of adverse effects can be increased when Sulfaphenazole is combined with Mecamylamine.
SulfapyridineThe risk or severity of adverse effects can be increased when Sulfapyridine is combined with Mecamylamine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Mecamylamine.
SulfisoxazoleThe risk or severity of adverse effects can be increased when Sulfisoxazole is combined with Mecamylamine.
SulfoxoneThe risk or severity of adverse effects can be increased when Sulfoxone is combined with Mecamylamine.
TadalafilTadalafil may increase the antihypertensive activities of Mecamylamine.
TetracyclineTetracycline may increase the neuromuscular blocking activities of Mecamylamine.
TobramycinTobramycin may increase the neuromuscular blocking activities of Mecamylamine.
TolazamideThe risk or severity of adverse effects can be increased when Tolazamide is combined with Mecamylamine.
TolbutamideThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Mecamylamine.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Mecamylamine.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Mecamylamine.
TreprostinilTreprostinil may increase the hypotensive activities of Mecamylamine.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Mecamylamine.
VardenafilVardenafil may increase the antihypertensive activities of Mecamylamine.
YohimbineYohimbine may decrease the antihypertensive activities of Mecamylamine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Struthers AM, Wilkinson JL, Dwoskin LP, Crooks PA, Bevins RA: Mecamylamine, dihydro-beta-erythroidine, and dextromethorphan block conditioned responding evoked by the conditional stimulus effects of nicotine. Pharmacol Biochem Behav. 2009 Dec;94(2):319-28. doi: 10.1016/j.pbb.2009.09.012. Epub 2009 Sep 22. [PubMed:19778551 ]
  5. Shytle RD, Penny E, Silver AA, Goldman J, Sanberg PR: Mecamylamine (Inversine): an old antihypertensive with new research directions. J Hum Hypertens. 2002 Jul;16(7):453-7. [PubMed:12080428 ]
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Drug created on June 13, 2005 07:24 / Updated on May 23, 2014 15:20