meprobamate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES.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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.847 Moderate 0.67
caco2-efflux Caco-2 efflux ratio (BA/AB) 2.056 Moderate 0.67
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 22.542 10^-6 cm/s Moderate 0.67
dh-clint Dog hepatocyte intrinsic clearance 2.630 uL/min/10^6 cells Moderate 0.67
dppb Dog plasma protein binding (% unbound) 85.310 % Moderate 0.67
fcs-ppb Fetal calf serum protein binding (% unbound) 84.210 % Moderate 0.67
herg hERG pIC50 4.132 pIC50 Moderate 0.67
hh-clint Human hepatocyte intrinsic clearance 1.742 uL/min/10^6 cells Moderate 0.67
hlm-clint Human liver microsomal intrinsic clearance 4.178 uL/min/mg protein Moderate 0.67
hppb Human plasma protein binding (% unbound) 89.640 % Moderate 0.67
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,MAP3K21,MAP3K7,MAPK7,NTRK2,PDK1,PDK2,PIK3CB,PIM2,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK 33
kinase-selectivity-class AXL,CAMK2D,CDK9,GRK2,STK33,TEK 6
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.571 Moderate 0.67
mh-clint Mouse hepatocyte intrinsic clearance 7.516 Moderate 0.67
mppb Mouse plasma protein binding (% unbound) 89.700 Moderate 0.67
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 7.889 Moderate 0.67
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 93.330 % Moderate 0.67
rh-clint Rat hepatocyte intrinsic clearance 1.507 uL/min/10^6 cells Moderate 0.67
rh-fuinc Rat hepatocyte fraction unbound in incubation 96.930 % Moderate 0.67
rppb Rat plasma protein binding (% unbound) 83.330 % Moderate 0.67
solubility-dd Solubility at pH 7.4 in DMSO 935.406 uM Moderate 0.67

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 484.67 46.14 178 1298 287668 90339303
Accidental overdose 195.16 46.14 52 1424 28221 90598750
Drug abuse 189.99 46.14 65 1411 82282 90544689
Completed suicide 154.17 46.14 65 1411 144993 90481978
Overdose 126.42 46.14 58 1418 157651 90469320
Accidental death 108.10 46.14 20 1456 2028 90624943
Respiratory arrest 83.23 46.14 28 1448 33283 90593688
Unresponsive to stimuli 71.94 46.14 26 1450 38095 90588876
Cardiac arrest 63.78 46.14 32 1444 104903 90522068
Pulmonary oedema 62.93 46.14 27 1449 62053 90564918
Drug screen positive 51.45 46.14 12 1464 3745 90623226

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
Toxicity to various agents 226.75 68.37 99 662 229037 42391537
Drug abuse 192.30 68.37 71 690 104700 42515874
Accidental overdose 158.80 68.37 45 716 28285 42592289
Respiratory arrest 123.10 68.37 37 724 28387 42592187
Cardiac arrest 74.63 68.37 37 724 109283 42511291
Overdose 69.97 68.37 35 726 105229 42515345

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 653.45 47.17 268 1911 480287 110106833
Drug abuse 369.53 47.17 136 2043 177275 110409845
Accidental overdose 325.01 47.17 92 2087 51742 110535378
Overdose 230.24 47.17 105 2074 233689 110353431
Respiratory arrest 183.29 47.17 61 2118 58238 110528882
Completed suicide 166.00 47.17 85 2094 242296 110344824
Cardiac arrest 125.86 47.17 66 2113 196687 110390433
Accidental death 97.16 47.17 22 2157 4987 110582133
Pulmonary oedema 82.48 47.17 40 2139 100619 110486501
Cardio-respiratory arrest 71.45 47.17 38 2141 115798 110471322
Pulmonary congestion 68.57 47.17 25 2154 30941 110556179
Unresponsive to stimuli 66.62 47.17 30 2149 63760 110523360
Drug screen positive 61.65 47.17 16 2163 6394 110580726
Death 48.69 47.17 64 2115 698805 109888315
Poisoning 48.16 47.17 19 2160 29086 110558034

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 D000927 Anticonvulsants
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 D011619 Psychotropic Drugs
MeSH PA D014151 Anti-Anxiety Agents
CHEBI has role CHEBI:35474 anxiolytic drug

Related Drugs by ATC class:

N05BC Carbamates 2 drugs
emylcamatemebutamate
N05CX Hypnotics and sedatives in combination, excl. barbiturates 5 drugs
clomethiazoledipiperonylaminoethanolemeproniummethaqualonemethylpentynol

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 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
7225 IUPHAR_LIGAND_ID
533 INN_ID
9I7LNY769Q UNII
6760 RXNORM
1904 MMSL
5051 MMSL
d00288 MMSL
001445 NDDF
387395007 SNOMEDCT_US
70864001 SNOMEDCT_US
9I7LNY769Q INXIGHT DRUGS

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