Details of the Drug

General Information of Drug (ID: DMHM93Y)

Drug Name

Meprobamate

Synonyms

meprobamate; Meprospan; Meprobamat; Equanil; Miltown; Amepromat; Meprocompren; Meproban; Tranmep; Meprobam; Dapaz; Metractyl; Meprotabs; Meprosin; Meprodil; Mepiosine; Libiolan; Crestanil; Calmiren; Ayeramate; Andaksin; Anatimon; Anathylmon; Holbamate; Despasmol; Cirponyl; Biobamat; Neuramate; Metranquil; Meprocon; Mepantin; Lepetown; Ipsotian; Equilium; Equatrate; Carbaxin; Biobamate; Ansiatan; Anastress; Miltamato; Meprotil; Meprotan; Meprosan; Meproleaf; Meprindon; Mepranil; Mepavlon; Margonil; Harmonin; Dicandiol; Calmadin; Auxietil; Anxietil; Ansiowas; Amepromat; Amosene; Andaxin; Aneural; Aneurol; Aneusral; Aneuxal; Aneuxral; Ansietan; Ansil; Anural; Anzil; Apascil; Apasil; Appetrol; Arcoban; Arpon; Artolon; Ataraxine; Atraxin; Ayermate; Bamate; Brobamate; Calmax; Cirpon; Coprobate; Cypron; Cyrpon; Deprol; Diron; Diurnal; Diurnaldiverondormabrol; Diveron; Dormabrol; Ecuanil; Edenal; Enorden; Epicur; Epikur; Equinil; Equitar; Erina; Estasil; Gadexyl; Gagexyl; Hartol; Kessobamate; Klort; Larten; Lepenil; Letyl; Mendel; Mepamtin; Meposed; Mepriam; Meprin; Meprobamato; Meprobamatum; Meprodiol; Meprol; Meprosa; Meprotanum; Meproten; Meprovan; Meprovanmeprozine; Meprozine; Meptran; Meptranactylmilprem; Micrainin; Milpath; Milprem; Miltann; Miltaun; Miltuan; Miltwon; Misedant; Morbam; Multaun; Nephentine; Nervonus; Oasil; Optarket;Orlevol; Orolevol; Pancalma; Panediol; Pankalma; Pathibamate; Paxin; Pensive; Perequietil; Perequil; Perquietil; Pertranquil; Pimal; Placidon; Placitate; Prequil; Probamato; Probamyl; Probate; Procalmadiol; Procalmadol; Procalmidol; Procarbamide; Promate; Promato; Proquanil; Protran; Quaname; Quanane; Quanil; Quietidon; Quivet; Rastenil; Reostral; Restenil; Restenyl; Restinal; Restinil; Robamate;Sadanyl; Scolazil; Sedabamate; Sedanil; Sedanyl; Sedazil; Sedoquil; Sedoselecta; Selene; Seril; Setran; Shalvaton; Sowell; Spantran; Stensolo; Tamate; Tensol; Tensonal; Trancot; Trankvilan; Tranlisant; Tranquilan; Tranquilate; Tranquilax; Tranquiline; Tranquilsan; Tranquinol; Trelmar; Urbil; Urbilat; Vistabamate; Wardamate; Wyseals; Zirpon; Component of Appetrol; Component of Bamadex; Component of Equalysen; Component of Milpath; Component of Milprem; Component of Miltrate; Equanil suspension; Meprobamat [German]; Meprobamate and Aspirin Tablets; Meprobamato [Italian]; Meprobamic acid; Meprocon CMC; Solevione anastress; Bamd 400; Bamo 400; Canquil 400; Miltown 600; PMB 200; PMB 400; Apo-Meprobamate; Appetrol-Sr; Canquil-400; Component of PMB-400; Equanil (TN); Equazine-M; Fas-Cile; Fas-Cile 200; Kesso-Bamate; Mar-Bate; Meprin (VAN); Mepro-Aspirin; Mepro-analgesic; Meprobamato [INN-Spanish]; Meprobamatum [INN-Latin]; Meprospan (TN); Meprospan-200; Meprospan-400; Milprem-200; Milprem-400; Miltown (TN); My-trans; Neo-Tran; PMB-200; PMB-400; Pan-tranquil; Q-Gesic; SK-Bamate; Tranquiline (Intra); Vio-Bamate; Cap-O-Tran; Carbamic acid 2-methyl-2-propyltrimethylene ester; Meprobamate (JAN/USP/INN); Meprobamate [USAN:INN:BAN:JAN]; Carbamic acid, 2-methyl-2-propyltrimethylene ester; [2-(carbamoyloxymethyl)-2-methylpentyl] carbamate; {2-[(carbamoyloxy)methyl]-2-methylpentyl} carbamate; 1,3-Propanediol, 2-methyl-2-propyl-, 1,3-dicarbamate; 1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate; 2,2-Di(carbamoyloxymethyl)pentane; 2-Methyl-2-n-propyl-1,3-propanediol dicarbamate; 2-Methyl-2-propyl-1,3-propanediol dicarbamate; 2-Methyl-2-propylpropane-1,3-diol dicarbamate; 2-Methyl-2-propyltrimethylene carbamate; 2-Metil-2-n-propil-1,3-propanediol dicarbamato; 2-Metil-2-n-propil-1,3-propanediol dicarbamato [Spanish]; 2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate; 3P Bamate; KAI-1455

Indication

Disease Entry	ICD 11	Status	REF
Anxiety	N.A.	Approved	[1]
Anxiety disorder	6B00-6B0Z	Approved	[2]
Malaria	1F40-1F45	Approved	[3]
Ischemic reperfusion injury	DB98.B	Discontinued in Phase 1	[4]
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Therapeutic Class

Antianxiety Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

218.25

Logarithm of the Partition Coefficient (xlogp)

0.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is well absorbed from the gastrointestinal tract []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.6 mL/min/kg [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 10 hours [6]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 157.0936 micromolar/kg/day [7]
Unbound Fraction: The unbound fraction of drug in plasma is 1% [6]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.7 L/kg [6]
Water Solubility: The ability of drug to dissolve in water is measured as 3.4 mg/mL [5]

Chemical Identifiers

Formula: C9H18N2O4
IUPAC Name: [2-(carbamoyloxymethyl)-2-methylpentyl] carbamate
Canonical SMILES: CCCC(C)(COC(=O)N)COC(=O)N
InChI: InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
InChIKey: NPPQSCRMBWNHMW-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4064
ChEBI ID: CHEBI:6761
CAS Number: 57-53-4
DrugBank ID: DB00371
TTD ID: D0Y4AW
INTEDE ID: DR1029
ACDINA ID: D00398

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor alpha-1 (GABRA1)	TT1MPAY	GBRA1_HUMAN	Antagonist	[8]
Polypeptide deformylase (PDF)	TT9SL3Q	DEFM_HUMAN	Inhibitor	[3]
Protein kinase C epsilon (PRKCE)	TTBZ7OD	KPCE_HUMAN	Stimulator	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2E1 (CYP2E1)	DEVDYN7	CP2E1_HUMAN	Substrate	[10]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[11]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[12]

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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 Meprobamate (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Major	Additive CNS depression effects by the combination of Meprobamate and Oliceridine.	Acute pain [MG31]	[13]
Dihydrocodeine	DMB0FWL	Major	Additive CNS depression effects by the combination of Meprobamate and Dihydrocodeine.	Chronic pain [MG30]	[14]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Meprobamate and Olopatadine.	Conjunctiva disorder [9A60]	[15]
Propofol	DMB4OLE	Moderate	Additive CNS depression effects by the combination of Meprobamate and Propofol.	Corneal disease [9A76-9A78]	[16]
Alfentanil	DMVO0UB	Major	Additive CNS depression effects by the combination of Meprobamate and Alfentanil.	Corneal disease [9A76-9A78]	[13]
Remifentanil	DMZTXCH	Major	Additive CNS depression effects by the combination of Meprobamate and Remifentanil.	Corneal disease [9A76-9A78]	[13]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Meprobamate and Esketamine.	Depression [6A70-6A7Z]	[17]
Brimonidine	DMQLT4N	Moderate	Additive CNS depression effects by the combination of Meprobamate and Brimonidine.	Glaucoma [9C61]	[18]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Meprobamate and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[19]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Meprobamate and Lasmiditan.	Migraine [8A80]	[20]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Meprobamate and Flibanserin.	Mood disorder [6A60-6E23]	[21]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Meprobamate and Thalidomide.	Multiple myeloma [2A83]	[22]
Levomethadyl Acetate	DM06HG5	Major	Additive CNS depression effects by the combination of Meprobamate and Levomethadyl Acetate.	Opioid use disorder [6C43]	[14]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Meprobamate and Apraclonidine.	Optic nerve disorder [9C40]	[18]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Meprobamate and Dextropropoxyphene.	Pain [MG30-MG3Z]	[23]
Butorphanol	DM5KYPJ	Major	Additive CNS depression effects by the combination of Meprobamate and Butorphanol.	Pain [MG30-MG3Z]	[13]
Oxymorphone	DM65AGJ	Major	Additive CNS depression effects by the combination of Meprobamate and Oxymorphone.	Pain [MG30-MG3Z]	[13]
Levorphanol	DMGS80V	Major	Additive CNS depression effects by the combination of Meprobamate and Levorphanol.	Pain [MG30-MG3Z]	[13]
Dezocine	DMJDB0Y	Major	Additive CNS depression effects by the combination of Meprobamate and Dezocine.	Pain [MG30-MG3Z]	[13]
Nalbuphine	DMOSQGU	Major	Additive CNS depression effects by the combination of Meprobamate and Nalbuphine.	Pain [MG30-MG3Z]	[13]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Meprobamate and Buprenorphine.	Pain [MG30-MG3Z]	[24]
Hydrocodone	DMQ2JO5	Major	Additive CNS depression effects by the combination of Meprobamate and Hydrocodone.	Pain [MG30-MG3Z]	[13]
Meperidine	DMX4GND	Major	Additive CNS depression effects by the combination of Meprobamate and Meperidine.	Pain [MG30-MG3Z]	[13]
Oxycodone	DMXLKHV	Major	Additive CNS depression effects by the combination of Meprobamate and Oxycodone.	Pain [MG30-MG3Z]	[13]
Fentanyl	DM8WAHT	Major	Additive CNS depression effects by the combination of Meprobamate and Fentanyl.	Sensation disturbance [MB40]	[13]
Sufentanil	DMU7YEL	Major	Additive CNS depression effects by the combination of Meprobamate and Sufentanil.	Sensation disturbance [MB40]	[13]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Meprobamate 200 mg tablet	200 mg	Oral Tablet	Oral
Meprobamate 400 mg tablet	400 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Meprobamate FDA Label
2	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: 7225).
3	The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
4	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800026294)
5	BDDCS applied to over 900 drugs
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	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
8	DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
9	Protein kinase C, an elusive therapeutic target . Nat Rev Drug Discov. 2012 December; 11(12): 937-957.
10	Mechanisms of circadian rhythmicity of carbon tetrachloride hepatotoxicity. J Pharmacol Exp Ther. 2002 Jan;300(1):273-81.
11	Solid-phase synthesis of drug glucuronides by immobilized glucuronosyltransferase. J Med Chem. 1976 May;19(5):679-83.
12	Association between blood carisoprodol:meprobamate concentration ratios and CYP2C19 genotype in carisoprodol-drugged drivers: decreased metabolic capacity in heterozygous CYP2C191/CYP2C192 subjects? Pharmacogenetics. 2003 Jul;13(7):383-8.
13	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
14	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
15	Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
16	Gill SS, Wright EM, Reilly CS "Pharmacokinetic interaction of propofol and fentanyl: single bolus injection study." Br J Anaesth 65 (1990): 760-5. [PMID: 2265045]
17	Cerner Multum, Inc. "Australian Product Information.".
18	Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
19	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
20	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
21	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
22	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
23	Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
24	Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]