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], [2]

Therapeutic Class

Antihypertensive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

211.26

Topological Polar Surface Area (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 [3]

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	[4]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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]	[15]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Methoxamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[16]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Levomilnacipran.	Chronic pain [MG30]	[17]
Selegiline	DM6034S	Moderate	Additive hypertensive effects by the combination of Methoxamine and Selegiline.	Depression [6A70-6A7Z]	[15]
Isocarboxazid	DMAF1NB	Moderate	Additive hypertensive effects by the combination of Methoxamine and Isocarboxazid.	Depression [6A70-6A7Z]	[15]
Milnacipran	DMBFE74	Moderate	Additive hypertensive effects by the combination of Methoxamine and Milnacipran.	Depression [6A70-6A7Z]	[17]
Tranylcypromine	DMGB5RE	Moderate	Additive hypertensive effects by the combination of Methoxamine and Tranylcypromine.	Depression [6A70-6A7Z]	[18]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Desvenlafaxine.	Depression [6A70-6A7Z]	[17]
Phenelzine	DMHIDUE	Moderate	Additive hypertensive effects by the combination of Methoxamine and Phenelzine.	Depression [6A70-6A7Z]	[15]
Procarbazine	DMIK367	Moderate	Additive hypertensive effects by the combination of Methoxamine and Procarbazine.	Hodgkin lymphoma [2B30]	[15]
Ozanimod	DMT6AM2	Moderate	Additive hypertensive effects by the combination of Methoxamine and Ozanimod.	Multiple sclerosis [8A40]	[15]
Sibutramine	DMFJTDI	Moderate	Increased risk of rapid heart rate by the combination of Methoxamine and Sibutramine.	Obesity [5B80-5B81]	[19]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Methoxamine and Rasagiline.	Parkinsonism [8A00]	[15]
-----------


⏷ Show the Full List of 13 DDI Information of This Drug

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	Drug information of Methoxamine, 2008. eduDrugs.
3	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
4	Activation of alpha1-adrenoceptors inhibits growth hormone secretion in humans. Exp Clin Endocrinol Diabetes. 2009 Oct;117(9):460-2.
5	Mirtazapine treatment after conditioning with methamphetamine alters subsequent expression of place preference. Drug Alcohol Depend. 2009 Jan 1;99(1-3):231-9.
6	Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91.
7	Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
8	A structure-activity relationship study of benzylic modifications of 4-[1-(1-naphthyl)ethyl]-1H-imidazoles on alpha 1- and alpha 2-adrenergic recep... J Med Chem. 1994 Jul 22;37(15):2328-33.
9	3-Benzisothiazolylpiperazine derivatives as potential atypical antipsychotic agents. J Med Chem. 1996 Jan 5;39(1):143-8.
10	An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment o... J Med Chem. 2006 Jun 1;49(11):3116-35.
11	A new arylpiperazine antipsychotic with high D2/D3/5-HT1A/alpha 1A-adrenergic affinity and a low potential for extrapyramidal effects. J Med Chem. 1994 Apr 15;37(8):1060-2.
12	Drug repositioning: identifying and developing new uses for existing drugs. Nat Rev Drug Discov. 2004 Aug;3(8):673-83.
13	Alpha- and beta-adrenoceptors: from the gene to the clinic. 2. Structure-activity relationships and therapeutic applications. J Med Chem. 1995 Sep 15;38(19):3681-716.
14	Alpha- and beta-adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification. J Med Chem. 1995 Sep 1;38(18):3415-44.
15	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
16	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
17	Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
18	Goldberg LI "Monoamine oxidase inhibitors: adverse reactions and possible mechanisms." JAMA 190 (1964): 456-62. [PMID: 14197995]
19	Mendelson J, Jones RT, Upton R, Jacob P 3rd "Methamphetamine and ethanol interactions in humans." Clin Pharmacol Ther 57 (1995): 559-68. [PMID: 7768079]