meprobamate ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
tranquillizers, propanediol and pentanediol derivatives 1704 57-53-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • meprobamate
  • meprobam
  • meprobamat
  • meproban
  • meprocompren
A carbamate with hypnotic, sedative, and some muscle relaxant properties, although in therapeutic doses reduction of anxiety rather than a direct effect may be responsible for muscle relaxation. Meprobamate has been reported to have anticonvulsant actions against petit mal seizures, but not against grand mal seizures (which may be exacerbated). It is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES. (From Martindale, The Extra Pharmacopoeia, 30th ed, p603)
  • Molecular weight: 218.25
  • Formula: C9H18N2O4
  • CLOGP: 0.92
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 104.64
  • ALOGS: -1.95
  • ROTB: 8

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.40 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 157.09 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 14 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 28, 1955 FDA MEDPOINTE PHARM HLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 426.51 46.36 171 1189 212328 50391436
Accidental overdose 183.86 46.36 51 1309 19482 50584282
Drug abuse 174.82 46.36 64 1296 59782 50543982
Completed suicide 129.04 46.36 65 1295 131824 50471940
Overdose 117.95 46.36 56 1304 99671 50504093
Accidental death 101.32 46.36 20 1340 1724 50602040
Respiratory arrest 72.40 46.36 28 1332 29981 50573783
Unresponsive to stimuli 61.39 46.36 25 1335 30584 50573180
Pulmonary oedema 56.15 46.36 27 1333 48911 50554853
Cardiac arrest 55.56 46.36 32 1328 83619 50520145

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 190.92 60.54 71 638 79812 29494006
Toxicity to various agents 183.52 60.54 86 623 173575 29400243
Accidental overdose 143.64 60.54 40 669 17553 29556265
Respiratory arrest 111.77 60.54 36 673 25797 29548021
Cardiac arrest 72.94 60.54 37 672 85554 29488264

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 505.68 42.09 236 1769 363277 64133450
Drug abuse 344.73 42.09 135 1870 132239 64364488
Accidental overdose 300.77 42.09 87 1918 33470 64463257
Overdose 163.09 42.09 85 1920 159481 64337246
Respiratory arrest 158.23 42.09 60 1945 52925 64443802
Completed suicide 136.03 42.09 85 1920 224329 64272398
Cardiac arrest 112.87 42.09 66 1939 153998 64342729
Accidental death 93.67 42.09 22 1983 3703 64493024
Pulmonary oedema 74.58 42.09 40 1965 78634 64418093
Pulmonary congestion 63.81 42.09 25 1980 23855 64472872
Cardio-respiratory arrest 61.11 42.09 38 1967 98355 64398372
Unresponsive to stimuli 57.39 42.09 29 1976 50364 64446363
Drug screen positive 51.74 42.09 15 1990 5714 64491013
Poisoning 45.03 42.09 19 1986 21860 64474867
Death 42.98 42.09 63 1942 482642 64014085

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05BC01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Carbamates
ATC N05BC51 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Carbamates
ATC N05CX01 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Hypnotics and sedatives in combination, excl. barbiturates
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D009125 Muscle Relaxants, Central
MeSH PA D009465 Neuromuscular Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Anxiety indication 48694002
Anxiety associated with Menopause indication
Pain with Tension and Anxiety indication
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Hypercholesterolemia contraindication 13644009
Lowered convulsive threshold contraindication 19260006
Myocardial infarction contraindication 22298006 DOID:5844
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Dementia contraindication 52448006
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Acute nephropathy contraindication 58574008
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Substance abuse contraindication 66214007
Diabetes mellitus contraindication 73211009 DOID:9351
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Uterine leiomyoma contraindication 95315005 DOID:13223
Anemia due to enzyme deficiency contraindication 111577008
Deep venous thrombosis contraindication 128053003
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Endometriosis contraindication 129103003
Mammography abnormal contraindication 168750009
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Acute intermittent porphyria contraindication 234422006 DOID:3890
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Endometrial carcinoma contraindication 254878006 DOID:2871
Chorea contraindication 271700006
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Acute erosive gastritis contraindication 444926003
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

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
GABA-A receptor alpha-2/beta-3/gamma-2 Ion channel AGONIST WOMBAT-PK CHEMBL
GABA-A receptor alpha-3/beta-3/gamma-2 Ion channel AGONIST WOMBAT-PK CHEMBL
GABA-A receptor alpha-5/beta-3/gamma-2 Ion channel AGONIST WOMBAT-PK CHEMBL
GABA-A receptor alpha-1/beta-3/gamma-2 Ion channel AGONIST WOMBAT-PK CHEMBL
Multidrug resistance protein 1 Transporter IC50 6.82 WOMBAT-PK

External reference:

IDSource
4017913 VUID
N0000146264 NUI
D00376 KEGG_DRUG
4017913 VANDF
C0025386 UMLSCUI
CHEBI:6761 CHEBI
CHEMBL979 ChEMBL_ID
DB00371 DRUGBANK_ID
D008620 MESH_DESCRIPTOR_UI
4064 PUBCHEM_CID
533 INN_ID
7225 IUPHAR_LIGAND_ID
9I7LNY769Q UNII
6760 RXNORM
1904 MMSL
5051 MMSL
d00288 MMSL
001445 NDDF
387395007 SNOMEDCT_US
70864001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MEPROBAMATE Human Prescription Drug Label 1 46708-019 TABLET 200 mg ORAL ANDA 12 sections
MEPROBAMATE Human Prescription Drug Label 1 46708-020 TABLET 400 mg ORAL ANDA 12 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 51672-4147 TABLET 200 mg ORAL ANDA 14 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 51672-4148 TABLET 400 mg ORAL ANDA 14 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 52549-4147 TABLET 200 mg ORAL ANDA 17 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 52549-4148 TABLET 400 mg ORAL ANDA 17 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 55111-640 TABLET 200 mg ORAL ANDA 12 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 55111-641 TABLET 400 mg ORAL ANDA 12 sections
Meprobamate Human Prescription Drug Label 1 62332-019 TABLET 200 mg ORAL ANDA 12 sections
Meprobamate Human Prescription Drug Label 1 62332-020 TABLET 400 mg ORAL ANDA 12 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 69097-974 TABLET 200 mg ORAL ANDA 13 sections
Meprobamate HUMAN PRESCRIPTION DRUG LABEL 1 69097-975 TABLET 400 mg ORAL ANDA 13 sections