Details of the Drug

General Information of Drug (ID: DMGQFYB)

Drug Name

Mecamylamine

Synonyms

Mecamilamina; Mecamine; Mecamylaminum; Mekamine; Mevasine; Revertina; Versamine; Inversine hydrochloride; Mecamilamina [DCIT]; Mecamilamina [Italian]; Mevasin hydrochloride; Inversine (TN); Mecamylamine [INN:BAN]; Mecamylaminum [INN-Latin]; N-Methyl-2-isocamphanamine; N,2,3,3-Tetramethyl-2-norbornamine; N,2,3,3-Tetramethyl-2-norcamphanamine; N,2,2,3-tetramethylbicyclo[2.2.1]heptan-3-amine; N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine; 2-Methylamino-2,3,3-trimethylnorbornane; 2-Methylaminoisocamphane; 3-Methylaminoisocamphane; 3-Methylaminoisokamfan; 3-Methylaminoisokamfan [Czech]; 3-beta-Methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane

Indication

Disease Entry	ICD 11	Status	REF
Essential hypertension	BA00	Approved	[1]

Therapeutic Class

Antihypertensive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

167.29

Topological Polar Surface Area (xlogp)

2.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [2]
Elimination: 50% of drug is excreted from urine in the unchanged form [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.75245 micromolar/kg/day [4]
Water Solubility: The ability of drug to dissolve in water is measured as 212 mg/mL [3]

Chemical Identifiers

Formula: C11H21N
IUPAC Name: N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
Canonical SMILES: CC1(C2CCC(C2)C1(C)NC)C
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
InChIKey: IMYZQPCYWPFTAG-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4032
ChEBI ID: CHEBI:6706
CAS Number: 60-40-2
DrugBank ID: DB00657
TTD ID: D0V8HA
ACDINA ID: D00386

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Nicotinic acetylcholine receptor (nAChR)	TTJSZTB	NOUNIPROTAC	Antagonist	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Mecamylamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Mecamylamine caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[15]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Mecamylamine caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[15]
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Cariprazine.	Bipolar disorder [6A60]	[16]
Selegiline	DM6034S	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Selegiline.	Depression [6A70-6A7Z]	[17]
Isocarboxazid	DMAF1NB	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Isocarboxazid.	Depression [6A70-6A7Z]	[17]
Tranylcypromine	DMGB5RE	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Tranylcypromine.	Depression [6A70-6A7Z]	[17]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Mecamylamine and OPC-34712.	Depression [6A70-6A7Z]	[16]
Phenelzine	DMHIDUE	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Phenelzine.	Depression [6A70-6A7Z]	[17]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Mecamylamine caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[15]
Procarbazine	DMIK367	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Procarbazine.	Hodgkin lymphoma [2B30]	[17]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Mecamylamine caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[15]
Propiomazine	DMKY8V1	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Propiomazine.	Insomnia [7A00-7A0Z]	[16]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Mecamylamine and ITI-007.	Insomnia [7A00-7A0Z]	[16]
Ozanimod	DMT6AM2	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Ozanimod.	Multiple sclerosis [8A40]	[17]
Promethazine	DM6I5GR	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Promethazine.	Nausea/vomiting [MD90]	[16]
Safinamide	DM0YWJC	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Safinamide.	Parkinsonism [8A00]	[17]
Rasagiline	DM3WKQ4	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Rasagiline.	Parkinsonism [8A00]	[17]
Levomepromazine	DMIKFEL	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Levomepromazine.	Psychotic disorder [6A20-6A25]	[16]
Quetiapine	DM1N62C	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Quetiapine.	Schizophrenia [6A20]	[16]
Mesoridazine	DM2ZGAN	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Mesoridazine.	Schizophrenia [6A20]	[16]
Thioridazine	DM35M8J	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Thioridazine.	Schizophrenia [6A20]	[16]
Aripiprazole	DM3NUMH	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Aripiprazole.	Schizophrenia [6A20]	[16]
Iloperidone	DM6AUFY	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Iloperidone.	Schizophrenia [6A20]	[16]
Paliperidone	DM7NPJS	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Paliperidone.	Schizophrenia [6A20]	[16]
Perphenazine	DMA4MRX	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Perphenazine.	Schizophrenia [6A20]	[16]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Molindone.	Schizophrenia [6A20]	[16]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Thiothixene.	Schizophrenia [6A20]	[16]
Trifluoperazine	DMKBYWI	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Trifluoperazine.	Schizophrenia [6A20]	[16]
Risperidone	DMN6DXL	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Risperidone.	Schizophrenia [6A20]	[16]
Amisulpride	DMSJVAM	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Amisulpride.	Schizophrenia [6A20]	[16]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Asenapine.	Schizophrenia [6A20]	[16]
Methdilazine	DMAUHQX	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[16]
Trimeprazine	DMEMV9D	Moderate	Additive hypotensive effects by the combination of Mecamylamine and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[18]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Quinoline yellow WS	E00309	24671	Colorant
Sunset yellow FCF	E00255	17730	Colorant
Brushite	E00392	104805	Diluent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Mecamylamine 2.5 mg tablet	2.5 mg	Oral Tablet	Oral
Mecamylamine Hydrochloride 2.5mg tablet	2.5mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3	BDDCS applied to over 900 drugs
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Mecamylamine (Inversine): an old antihypertensive with new research directions. J Hum Hypertens. 2002 Jul;16(7):453-7.
6	Atypical antipsychotics as noncompetitive inhibitors of alpha4beta2 and alpha7 neuronal nicotinic receptors. Neuropharmacology. 2009 Aug;57(2):183-91.
7	Functional versus chemical diversity: is biodiversity important for drug discovery. Trends Pharmacol Sci. 2002 May;23(5):225-31.
8	Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52.
9	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
10	The pipeline and future of drug development in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):904-22.
11	EP patent application no. 2774991, Drug delivery system for use in the treatment or diagnosis of neurological disorders.
12	Effects of ASM-024, a modulator of acetylcholine receptor function, on airway responsiveness and allergen-induced responses in patients with mild asthma. Can Respir J. 2015 Jul-Aug;22(4):230-4.
13	Therapeutic advances in the treatment of nicotine addiction: present and future. Ther Adv Chronic Dis. 2010 May; 1(3): 95-106.
14	Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92.
15	Allanby KD, Trounce JR "Excretion of mecamylamine after intravenous and oral administration." Br Med J 2 (1957): 1219-21. [PMID: 13472094]
16	Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
17	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
18	Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.