mecamylamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1646 60-40-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mecamylamine
  • mecamine
  • revertina
  • mecamylamine hydrochloride
  • mecamylamine HCl
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.
  • Molecular weight: 167.30
  • Formula: C11H21N
  • CLOGP: 2.82
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 1
  • TPSA: 12.03
  • ALOGS: -3.13
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 0 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 212 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.75 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 1, 1956 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC C02BB01 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, GANGLION-BLOCKING
Secondary and tertiary amines
FDA EPC N0000175641 Autonomic Ganglionic Blocker
FDA PE N0000175644 Decreased Autonomic Ganglionic Activity
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D005730 Ganglionic Blockers
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018733 Nicotinic Antagonists
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Neuronal acetylcholine receptor; alpha3/beta4 Ion channel NEGATIVE ALLOSTERIC MODULATOR Ki 6.22 WOMBAT-PK CHEMBL
Neuronal acetylcholine receptor; alpha4/beta4 Ion channel BLOCKER IC50 6.48 IUPHAR
Neuronal acetylcholine receptor; alpha4/beta2 Ion channel Ki 5.60 WOMBAT-PK
Neuronal acetylcholine receptor subunit alpha-7 Ion channel Ki 5.16 WOMBAT-PK
Neuronal acetylcholine receptor subunit alpha-6 Ion channel BLOCKER IC50 4.96 IUPHAR
Neuronal acetylcholine receptor subunit alpha-3 Ion channel BLOCKER IC50 6.41 IUPHAR
Neuronal acetylcholine receptor subunit alpha-4 Ion channel BLOCKER IC50 6.48 IUPHAR
Acetylcholine receptor subunit alpha Ion channel BLOCKER IC50 5.82 IUPHAR
Neuronal acetylcholine receptor; alpha3/beta2 Ion channel IC50 6.55 CHEMBL
Neuronal acetylcholine receptor; alpha2/beta4 Ion channel IC50 5.51 CHEMBL
Neuronal acetylcholine receptor; alpha3/alpha6/beta2/beta3 Ion channel IC50 4.96 CHEMBL
Acetylcholine receptor subunit alpha Ion channel IC50 6.22 CHEMBL

External reference:

IDSource
4019807 VUID
N0000147896 NUI
C0025029 UMLSCUI
D00611 KEGG_DRUG
4956DJR58O UNII
826-39-1 SECONDARY_CAS_RN
542 INN_ID
73277004 SNOMEDCT_US
4019807 VANDF
6673 RXNORM
372828008 SNOMEDCT_US
d00739 MMSL
004499 NDDF
4032 PUBCHEM_CID
CHEBI:6706 CHEBI
CHEMBL267936 ChEMBL_ID
DB00657 DRUGBANK_ID
CHEMBL1237082 ChEMBL_ID
CHEMBL1398031 ChEMBL_ID
D008464 MESH_DESCRIPTOR_UI
3990 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mecamylamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0722-7183 TABLET 2.50 mg ORAL ANDA 11 sections
Vecamyl HUMAN PRESCRIPTION DRUG LABEL 1 45043-558 TABLET 2.50 mg ORAL ANDA 11 sections
Vecamyl HUMAN PRESCRIPTION DRUG LABEL 1 69413-558 TABLET 2.50 mg ORAL ANDA 11 sections