Details of the Drug

General Information of Drug (ID: DMF5XQH)

• Drug Name: Methoxamine
• Synonyms: Methoxamedrin; Methoxamedrine; Methoxamin; Methoxaminum; Metossamina; Metoxamina; Pseudomethoxamine; Vasoxin; Vasoxine; Metossamina [DCIT]; Methoxamine (BAN); Methoxamine [INN:BAN]; Methoxaminum [INN-Latin]; Metoxamina [INN-Spanish]; AQ-387/40213491; Alpha-(1-Aminoethyl)-2,5-dimethoxybenzyl alcohol; DL-2-Amino-1-(2,5-dimethoxyphenyl)propanol; 2-Amino-1-(2,5-dimethoxyphenyl)-1-propanol; 2-Amino-1-(2,5-dimethoxyphenyl)propanol; 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol; 2-amino-1-[2,5-bis(methyloxy)phenyl]propan-1-ol

Indication

Disease Entry	ICD 11	Status	REF
Hypertension	BA00-BA04	Approved	[1]

• Therapeutic Class: Antihypertensive Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 211.26
  Logarithm of the Partition Coefficient (xlogp); 0.5
  Rotatable Bond Count (rotbonds); 4
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 4
• ADMET Property: MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.57623 micromolar/kg/day [2]
• Chemical Identifiers:
  Formula: C11H17NO3
  IUPAC Name: 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
  Canonical SMILES: CC(C(C1=C(C=CC(=C1)OC)OC)O)N
  InChI: InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3
  InChIKey: WJAJPNHVVFWKKL-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 6082
  ChEBI ID: CHEBI:6839
  CAS Number: 390-28-3
  DrugBank ID: DB00723
  TTD ID: D09GYT
  VARIDT ID: DR01182

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor alpha-1B (ADRA1B)	TTBRKXS	ADA1B_HUMAN	Stimulator	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Alpha-1D adrenergic receptor (ADRA1D)	OTW2CD1O	ADA1D_HUMAN	Protein Interaction/Cellular Processes	[4]

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Moderate	Additive hypertensive effects by the combination of Methoxamine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[5]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Methoxamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[6]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Levomilnacipran.	Chronic pain [MG30]	[7]
Selegiline	DM6034S	Moderate	Additive hypertensive effects by the combination of Methoxamine and Selegiline.	Depression [6A70-6A7Z]	[5]
Isocarboxazid	DMAF1NB	Moderate	Additive hypertensive effects by the combination of Methoxamine and Isocarboxazid.	Depression [6A70-6A7Z]	[5]
Milnacipran	DMBFE74	Moderate	Additive hypertensive effects by the combination of Methoxamine and Milnacipran.	Depression [6A70-6A7Z]	[7]
Tranylcypromine	DMGB5RE	Moderate	Additive hypertensive effects by the combination of Methoxamine and Tranylcypromine.	Depression [6A70-6A7Z]	[8]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Desvenlafaxine.	Depression [6A70-6A7Z]	[7]
Phenelzine	DMHIDUE	Moderate	Additive hypertensive effects by the combination of Methoxamine and Phenelzine.	Depression [6A70-6A7Z]	[5]
Procarbazine	DMIK367	Moderate	Additive hypertensive effects by the combination of Methoxamine and Procarbazine.	Hodgkin lymphoma [2B30]	[5]
Ozanimod	DMT6AM2	Moderate	Additive hypertensive effects by the combination of Methoxamine and Ozanimod.	Multiple sclerosis [8A40]	[5]
Sibutramine	DMFJTDI	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Sibutramine.	Obesity [5B80-5B81]	[9]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Methoxamine and Rasagiline.	Parkinsonism [8A00]	[5]

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 483).
• [2] 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
• [3] Activation of alpha1-adrenoceptors inhibits growth hormone secretion in humans. Exp Clin Endocrinol Diabetes. 2009 Oct;117(9):460-2.
• [4] Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane. Sci China C Life Sci. 2004 Aug;47(4):376-81. doi: 10.1360/03yc0109.
• [5] Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
• [6] Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
• [7] Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
• [8] Goldberg LI "Monoamine oxidase inhibitors: adverse reactions and possible mechanisms." JAMA 190 (1964): 456-62. [PMID: 14197995]
• [9] Mendelson J, Jones RT, Upton R, Jacob P 3rd "Methamphetamine and ethanol interactions in humans." Clin Pharmacol Ther 57 (1995): 559-68. [PMID: 7768079]