nabilone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
cannabinoid receptors agonists 1862 51022-71-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nabilone
  • cesamet
  • LY 109514
  • LY-109514
cannabinol deriv; RN given refers to cpd without isomeric designation; structure
  • Molecular weight: 372.55
  • Formula: C24H36O3
  • CLOGP: 6.72
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -5.88
  • ROTB: 6
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 mg O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 20 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility) 0.00 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 4.947 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.923 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.887 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 39.902 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.220 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.240 % High 1
herg hERG pIC50 5.051 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 31.842 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 63.096 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.600 % High 1
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 54
kinase-selectivity-class EIF2AK3,GRK2 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.457 High 1
mh-clint Mouse hepatocyte intrinsic clearance 72.611 High 1
mppb Mouse plasma protein binding (% unbound) 0.470 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.632 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.240 % High 1
rh-clint Rat hepatocyte intrinsic clearance 86.298 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 0.410 % High 1
rppb Rat plasma protein binding (% unbound) 0.440 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 1.698 uM High 1

Approvals:

DateAgencyCompanyOrphan
Dec. 26, 1985 FDA MEDA PHARMS

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
White blood cell count abnormal 354.91 23.56 84 5445 7420 90615498
Somatic symptom disorder 129.16 23.56 32 5497 3409 90619509
Musculoskeletal stiffness 128.01 23.56 121 5408 296411 90326507
Sacroiliitis 127.53 23.56 33 5496 4186 90618732
Gait disturbance 125.41 23.56 113 5416 260383 90362535
Rheumatoid arthritis 105.91 23.56 120 5409 362494 90260424
Insomnia 89.98 23.56 106 5423 333368 90289550
Drug hypersensitivity 82.48 23.56 120 5409 463489 90159429
Mood altered 82.04 23.56 33 5496 17111 90605807
Mean cell haemoglobin concentration abnormal 74.33 23.56 12 5517 136 90622782
Acute psychosis 73.59 23.56 20 5509 3058 90619860
Pain 70.97 23.56 174 5355 996167 89626751
Therapeutic product effect incomplete 70.20 23.56 72 5457 193824 90429094
Lip and/or oral cavity cancer 68.87 23.56 15 5514 907 90622011
Therapeutic response shortened 63.50 23.56 30 5499 22849 90600069
Cognitive disorder 61.04 23.56 43 5486 69364 90553554
Occult blood 58.41 23.56 14 5515 1297 90621621
Cannabinoid hyperemesis syndrome 52.76 23.56 8 5521 58 90622860
Anaphylactic reaction 52.17 23.56 43 5486 87481 90535437
Thyroid cancer 47.87 23.56 17 5512 6267 90616651
Psychotic disorder 43.91 23.56 26 5503 31204 90591714
Dystonia 43.46 23.56 21 5508 16798 90606120
Ankylosing spondylitis 32.73 23.56 16 5513 13117 90609801
Blood pressure increased 31.97 23.56 49 5480 197168 90425750
Iron deficiency 31.02 23.56 14 5515 9598 90613320
Dyskinesia 30.64 23.56 22 5507 36512 90586406
Eyelid haematoma 28.97 23.56 5 5524 87 90622831
Lichen sclerosus 28.62 23.56 8 5521 1355 90621563
Orthostatic hypotension 25.85 23.56 21 5508 41806 90581112
Eyelid injury 25.65 23.56 5 5524 174 90622744
Spinal osteoarthritis 24.48 23.56 15 5514 19133 90603785
Strabismus 23.94 23.56 8 5521 2460 90620458
Aplastic anaemia 23.92 23.56 13 5516 13256 90609662

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
Inspiratory capacity decreased 456.90 48.70 90 2930 2877 42615438
Pelvic pain 192.89 48.70 45 2975 3209 42615106
Terminal insomnia 166.55 48.70 32 2988 887 42617428
Injection site warmth 132.39 48.70 32 2988 2651 42615664
Kidney infection 103.06 48.70 32 2988 6738 42611577
Oral herpes 99.65 48.70 32 2988 7512 42610803
Neck pain 97.86 48.70 46 2974 29968 42588347
Ocular hyperaemia 96.91 48.70 38 2982 15925 42602390
Injection site mass 95.62 48.70 32 2988 8543 42609772
Musculoskeletal pain 93.25 48.70 46 2974 33294 42585021
Burning sensation 83.58 48.70 37 2983 20976 42597339
Dry eye 77.15 48.70 32 2988 15474 42602841
Injection site reaction 76.72 48.70 32 2988 15689 42602626
Drug ineffective 73.36 48.70 146 2874 630051 41988264
Feeling hot 70.42 48.70 34 2986 23448 42594867
Injection site erythema 69.02 48.70 32 2988 20163 42598152
Back pain 65.04 48.70 64 2956 141712 42476603
Chest injury 56.49 48.70 15 3005 1807 42616508
Pain 52.70 48.70 75 2945 244773 42373542
Cardiac disorder 49.55 48.70 35 2985 48897 42569418

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
Inspiratory capacity decreased 377.46 22.99 75 7648 2520 110579056
Terminal insomnia 148.59 22.99 33 7690 1905 110579671
Somatic symptom disorder 127.55 22.99 32 7691 3127 110578449
Pelvic pain 122.71 22.99 45 7678 15897 110565679
Sacroiliitis 117.67 22.99 33 7690 4945 110576631
Kidney infection 80.03 22.99 38 7685 25561 110556015
Injection site warmth 77.23 22.99 33 7690 17372 110564204
Injection site mass 72.27 22.99 35 7688 24578 110556998
Mood altered 70.72 22.99 33 7690 21342 110560234
Ankylosing spondylitis 70.59 22.99 30 7693 15582 110565994
Ocular hyperaemia 67.35 22.99 39 7684 39247 110542329
Lip and/or oral cavity cancer 63.03 22.99 15 7708 1175 110580401
Burning sensation 62.59 22.99 46 7677 69166 110512410
Acute psychosis 61.38 22.99 20 7703 4967 110576609
Oral herpes 59.68 22.99 35 7688 36045 110545531
Therapeutic response shortened 57.81 22.99 32 7691 29551 110552025
Musculoskeletal pain 55.32 22.99 66 7657 182957 110398619
Mean cell haemoglobin concentration abnormal 55.13 22.99 10 7713 203 110581373
Therapeutic product effect incomplete 53.82 22.99 72 7651 223733 110357843
Occult blood 51.69 22.99 14 7709 1842 110579734
Cannabinoid hyperemesis syndrome 49.11 22.99 8 7715 83 110581493
Cognitive disorder 49.06 22.99 44 7679 87467 110494109
Neck pain 48.51 22.99 51 7672 123079 110458497
Drug ineffective 46.55 22.99 219 7504 1520321 109061255
Thyroid cancer 45.81 22.99 17 7706 6197 110575379
Dry eye 45.80 22.99 35 7688 55758 110525818
Drug ineffective for unapproved indication 44.86 22.99 45 7678 102793 110478783
Feeling hot 43.71 22.99 42 7681 91064 110490512
Back pain 42.12 22.99 85 7638 370911 110210665
Blood pressure increased 41.76 22.99 69 7654 258304 110323272
Chest injury 39.25 22.99 13 7710 3396 110578180
Cardiac disorder 38.17 22.99 36 7687 76244 110505332
Pain 36.30 22.99 147 7576 954808 109626768
Arthralgia 36.22 22.99 128 7595 779504 109802072
Injection site erythema 35.29 22.99 38 7685 94138 110487438
Musculoskeletal stiffness 34.01 22.99 66 7657 279756 110301820
Dystonia 32.39 22.99 21 7702 25784 110555792
Injection site reaction 31.74 22.99 35 7688 89035 110492541
Psychotic disorder 31.32 22.99 27 7696 50910 110530666
Immune-mediated hepatitis 30.68 22.99 13 7710 6698 110574878
Incorrect dose administered 30.67 22.99 37 7686 103604 110477972
Joint swelling 29.06 22.99 82 7641 442763 110138813
Lichen sclerosus 28.77 22.99 8 7715 1160 110580416
Lower respiratory tract congestion 27.75 22.99 11 7712 4785 110576791
Strabismus 27.37 22.99 10 7713 3489 110578087
Eyelid haematoma 26.80 22.99 5 7718 119 110581457
Malaise 26.72 22.99 105 7618 671714 109909862
Eyelid injury 24.73 22.99 5 7718 183 110581393
Heart rate increased 24.00 22.99 39 7684 143795 110437781
Aplastic anaemia 23.88 22.99 17 7706 24291 110557285
Rash 23.72 22.99 14 7709 820950 109760626
Body temperature decreased 23.56 22.99 20 7703 36915 110544661

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC A04AD11 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
FDA CS M0003267 Cannabinoids
MeSH PA D000932 Antiemetics
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175782 Cannabinoid
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:74518 anti-obesity agent

Related Drugs by ATC class:

A04AD Other antiemetics 8 drugs
aprepitantcasopitantcerium oxalatechlorobutanoldronabinolmetopimazinerolapitantscopolamine

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Chemotherapy-induced nausea and vomiting indication 236084000
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Schizophrenia contraindication 58214004 DOID:5419
Hepatic failure contraindication 59927004
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Mania contraindication 231494001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.7 acidic

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
Cannabinoid receptor 1 GPCR AGONIST Ki 8.40 CHEMBL CHEMBL
Cannabinoid receptor 2 GPCR Ki 8.20 CHEMBL
Cannabinoid receptor 1 GPCR Ki 8.66 CHEMBL
Cannabinoid receptor 2 GPCR Ki 8.74 CHEMBL

External reference:

IDSource
4019352 VUID
N0000147524 NUI
D05099 KEGG_DRUG
4019352 VANDF
C0068333 UMLSCUI
CHEBI:135574 CHEBI
CHEMBL2218896 ChEMBL_ID
DB00486 DRUGBANK_ID
C011941 MESH_SUPPLEMENTAL_RECORD_UI
5284592 PUBCHEM_CID
9071 IUPHAR_LIGAND_ID
3930 INN_ID
2N4O9L084N UNII
31447 RXNORM
15778 MMSL
38357 MMSL
52672 MMSL
d04587 MMSL
001686 NDDF
322124005 SNOMEDCT_US
395806009 SNOMEDCT_US
2N4O9L084N INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cesamet HUMAN PRESCRIPTION DRUG LABEL 1 0187-1231 CAPSULE 1 mg ORAL NDA 22 sections